Title: Hotels in Chestertown, MD - Best Chestertown Hotels from £43 - Fully Refundable Options - Expedia.co.uk

 

[Chestertown Travel Guide](https://expedia.co.uk/Chestertown.dx7215)[Holiday Rentals in Chestertown](https://expedia.co.uk/Chestertown-Holiday-Rentals.d7215.Travel-Guide-HolidayRentals)[Chestertown Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chestertown.d7215.Car-Hire-Guide)[Chestertown Holidays](https://expedia.co.uk/Chestertown.d7215.Holidays-City-Breaks)

![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49/aerial-view-historic-waterfront-town-river-bridge-autumn.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find hotels in Chestertown, MD from £43

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## Go beyond your typical stay in Chestertown

Pet friendly

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-10&d1=2025-12-10&endDate=2025-12-12&d2=2025-12-12&amenities=PETS)

Pool

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-10&d1=2025-12-10&endDate=2025-12-12&d2=2025-12-12&amenities=POOL)

House­boat

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-10&d1=2025-12-10&endDate=2025-12-12&d2=2025-12-12&lodging=HOUSE_BOAT)

Hot tub

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-10&d1=2025-12-10&endDate=2025-12-12&d2=2025-12-12&amenities=HOT_TUB)

Apart­ment

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-10&d1=2025-12-10&endDate=2025-12-12&d2=2025-12-12&lodging=APARTMENT)

Cottage

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-10&d1=2025-12-10&endDate=2025-12-12&d2=2025-12-12&lodging=COTTAGE)

Family friendly

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-10&d1=2025-12-10&endDate=2025-12-12&d2=2025-12-12&travelerType=family_friendly)

Waterpark

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-10&d1=2025-12-10&endDate=2025-12-12&d2=2025-12-12&amenities=WATER_PARK)

## Check prices for these dates

Tonight

[26 Nov - 27 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2025-11-26&endDate=2025-11-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[27 Nov - 28 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2025-11-27&endDate=2025-11-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[28 Nov - 30 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top 10 Chestertown hotels and places to stay

![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast ](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/da06d995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/959c2292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn & Suites Chestertown

Chestertown

8.6/10

Excellent

(855)

"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Santa

£86

includes taxes & fees

30 Nov - 1 Dec

[](https://www.expedia.co.uk/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information)

![Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/25360cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/8b9992bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/cbce9d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Red Roof Inn & Suites Chestertown

Chestertown

7.2/10

Good

(417)

"This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Derek

£61

includes taxes & fees

3 Dec - 4 Dec

[](https://www.expedia.co.uk/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information)

![Private beach nearby, sun-loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/b3c72334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/72a73d25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/01b06110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach nearby, sun-loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/2b5c3ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Lodge at Great Oak Landing

Chestertown

8.0/10

Very good

(76)

"Very nice rooms, "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephania

£86

includes taxes & fees

2 Dec - 3 Dec

[](https://www.expedia.co.uk/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information)

![Front of property – evening/night](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/4ed42fd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/1af5cb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/44b6c861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/5800905c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Driftwood Inn

Chestertown

5.2/10

(175)

"Rooms are clean, staf was helpful "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Daryl

£54

includes taxes & fees

24 Dec - 25 Dec

[](https://www.expedia.co.uk/Chestertown-Hotels-Driftwood-Inn.h4862316.Hotel-Information)

![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/8051c714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Non Smoking | Premium bedding, in-room safe, desk, blackout curtains](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/bb9281c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/dfe0704f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/b1fff75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Rossville

7.0/10

Good

(1073)

"Easy check in and out. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrew

£56

includes taxes & fees

3 Dec - 4 Dec

[](https://www.expedia.co.uk/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/a8fad934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom | Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/6b94b388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/5139c564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

9.2/10

Wonderful

(925)

"nice, clean, up to date, budget friendly hotel"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

mike

£67

includes taxes & fees

1 Dec - 2 Dec

[](https://www.expedia.co.uk/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/7de3cb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/114f1de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/0c8b9f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/12e4e2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country Inn & Suites by Radisson, Baltimore North, MD

Rossville

7.2/10

Good

(1004)

"The reason I booked this hotel was because it had a hot tub and pool. These were both closed for "the season" without notification. If I knew that, I would have booked elsewhere. Everything else was just ok."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Brian

£73

includes taxes & fees

21 Dec - 22 Dec

[](https://www.expedia.co.uk/Baltimore-Hotels-Country-Inn-Suites-By-Radisson.h2410000.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/25ad1d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/05b80e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Two queen studio suite | Desk, blackout curtains, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/4152f194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

9.4/10

Exceptional

(1008)

"Would stay again"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dena

£69

includes taxes & fees

2 Dec - 3 Dec

[](https://www.expedia.co.uk/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information)

![Desk, free WiFi, bed sheets, alarm clocks](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast ](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/29162b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/abecbdac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/0c88ebfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn & Suites Bel Air I-95 Exit 77A

Edgewood

7.4/10

Good

(1024)

"Staff was very friendly. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ashlee

£54

includes taxes & fees

27 Nov - 28 Nov

[](https://www.expedia.co.uk/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite (2 Queen Beds with Sofa bed) | Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/65534781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/19c3b260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/a9a9ef59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Plus Hotel & Conference Center

Medford

7.8/10

Good

(1001)

"Yes I love how the room was, I had an amazing stay, the staff was nice and easy to manage I loved it thank you "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carmen

£79

includes taxes & fees

14 Dec - 15 Dec

[](https://www.expedia.co.uk/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/0fca1b7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast ](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/9f4cdea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/9c87ac97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/c6592633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn & Suites Aberdeen near APG

Aberdeen

7.8/10

Good

(799)

"The front desk staff were friendly and welcoming!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bonnie

£65

includes taxes & fees

21 Dec - 22 Dec

[](https://www.expedia.co.uk/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/47756559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, individually furnished, desk](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/6d549ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/8dff74ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/0ab02da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn & Suites Baltimore/Aberdeen

Aberdeen

9.0/10

Wonderful

(592)

"Wonderful room and location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Caren

£77

includes taxes & fees

19 Dec - 20 Dec

[](https://www.expedia.co.uk/Aberdeen-Hotels-Hampton-Inn-Suites-BaltimoreAberdeen.h15990289.Hotel-Information)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/c1cd1534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/ee9bd670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/1c55f3cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Americas Best Value Inn Edgewood

Edgewood

5.6/10

(1005)

"I love staying here. The prices are always reasonable, the staff are always so nice & helpful. The area is kept clean there's stores close to this hotel all around so convient! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christeena

£43

includes taxes & fees

27 Nov - 28 Nov

[](https://www.expedia.co.uk/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/367a733a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/d03cf3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/6468097d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/66a1e121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Kent Island Marina

Grasonville

9.0/10

Wonderful

(1003)

"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Roberta

£101

includes taxes & fees

3 Dec - 4 Dec

[](https://www.expedia.co.uk/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/9e72db94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/8890e17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/e60ed5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Place Kent Narrows & Marina

Grasonville

9.4/10

Exceptional

(663)

"My favorite hotel "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jen

£98

includes taxes & fees

30 Nov - 1 Dec

[](https://www.expedia.co.uk/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/180b8972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/5177cf8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Non Smoking (One-Bedroom) | In-room safe, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/fb66f5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Combined shower/bathtub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/e64b8ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Super 8 by Wyndham Aberdeen MD

Aberdeen

7.0/10

Good

(855)

"Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shelly

£43

includes taxes & fees

16 Dec - 17 Dec

[](https://www.expedia.co.uk/Aberdeen-Hotels-Super-8-By-Wyndham-Aberdeen-MD.h50106.Hotel-Information)

![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, desk, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/ad2aa516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/0dd46a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/7c3be532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott White Marsh

Nottingham

8.6/10

Excellent

(1005)

"Great place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

brian

£80

includes taxes & fees

10 Dec - 11 Dec

[](https://www.expedia.co.uk/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/dd2808c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, free cots/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/0707a932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/61b9d981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Combined shower/bathtub, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/304c53d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Super 8 by Wyndham Baltimore/Essex Area

Essex

5.4/10

(407)

"Just a nice quiet cool place clean rooms and the bed is away from the door lol"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jamelle

£66

includes taxes & fees

1 Dec - 2 Dec

[](https://www.expedia.co.uk/Baltimore-Hotels-Super-8-By-Wyndham-BaltimoreEssex-Area.h49889.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/932b25b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/b83d6711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One queen bed suite non smoking | Hypo-allergenic bedding, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/d9f316c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/e0847094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Baltimore/White Marsh

Nottingham

7.6/10

Good

(1008)

"Breakfast lady fabulous Staff very friendly "

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Alan

£77

includes taxes & fees

3 Dec - 4 Dec

[](https://www.expedia.co.uk/Baltimore-Hotels-Hampton-Inn-BaltimoreWhite-Marsh.h57004.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/600/507/ef21026e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, desk, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/600/507/0de2177e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/600/507/250ceaaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/600/507/e2e5d244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Aberdeen by IHG

Aberdeen

8.6/10

Excellent

(425)

"Kid friendly for sure! The room and hotel is clean and comfy, no complaints! Chlorine smell a bit strong in pool area but it didn’t bother me. We missed breakfast so not sure about that but everything else was great!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gabrielle

£93

includes taxes & fees

28 Nov - 29 Nov

[](https://www.expedia.co.uk/Aberdeen-Hotels-Holiday-Inn-Express-Aberdeen.h507.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.co.uk/Hotel-Search?startDate=2025-12-10&endDate=2025-12-11&regionId=7215&adults=2&sort=RECOMMENDED&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_FR-DE-MX-UK_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

Black Friday Sale

Save up to 40% on select hotels.

[Book now](https://expedia.co.uk/cheap-deals?rfrr=HTG_BF_PROMO_7215)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Hotels.d7215.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Hotels.d7215.Travel-Guide-Hotels)

## Stay near popular Chestertown attractions

[](https://www.expedia.co.uk/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels)

### Washington College

4.1/5 (45 reviews)

Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

[See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621561000403)

[](https://www.expedia.co.uk/Rolphs-Wharf-Marina-Hotels.0-l553248621561879605-0.Travel-Guide-Filter-Hotels)

### Rolphs Wharf Marina

Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.

[See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621561879605)

[](https://www.expedia.co.uk/Chestertown-Historic-District-Hotels.0-l950929327394992128-0.Travel-Guide-Filter-Hotels)

### Chestertown Historic District

Find out about the history of Chestertown with a stop at Chestertown Historic District. Experience the area's festivals and art scene.

[See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=950929327394992128)

[](https://www.expedia.co.uk/Crumpton-Auction-Hotels.0-l553248621532662415-0.Travel-Guide-Filter-Hotels)

### Crumpton Auction

Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area.

[See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621532662415)

[](https://www.expedia.co.uk/Historical-Society-Of-Kent-County-Maryland-Hotels.0-l553248621561000400-0.Travel-Guide-Filter-Hotels)

### Historical Society of Kent County Maryland

You can spend an afternoon browsing the exhibits at Historical Society of Kent County Maryland during your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

[See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621561000400)

[](https://www.expedia.co.uk/River-Arts-Chestertown-Hotels.0-l553248621532662298-0.Travel-Guide-Filter-Hotels)

### River Arts Chestertown

Enjoy the student vibe when you visit River Arts Chestertown during your trip to Chestertown. Take in the festivals in this family-friendly area.

[See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621532662298)

[](https://www.expedia.co.uk/Wilmer-Park-Hotels.0-l553248621561000402-0.Travel-Guide-Filter-Hotels)

### Wilmer Park

Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.

[See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621561000402)

[](https://www.expedia.co.uk/Kings-Town-Park-Hotels.0-l924439594043392000-0.Travel-Guide-Filter-Hotels)

### Kings Town Park

Kings Town Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.

[See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=924439594043392000)

## Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

[See all hotels in Chestertown](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-10&endDate=2025-12-11&adults=2&regionId=7215)

![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=900&h=314&p=1&q=high)

## Top Chestertown Hotel Reviews

![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg)

### Comfort Inn & Suites Chestertown

10/10 Excellent

"N/A"

[](https://expedia.co.uk/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information)

![Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg)

### Pendry Baltimore

10/10 Excellent

"Clean room, valet services, front desk, restaurant bar service"

[](https://expedia.co.uk/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information)

![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg)

### Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent

"Clean and quiet "

[](https://expedia.co.uk/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information)

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg)

### Historic Inns of Annapolis

10/10 Excellent

"Good location"

[](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information)

![Hampton Inn Baltimore Bayview Campus](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/e92cee9e_y.jpg)

### Hampton Inn Baltimore Bayview Campus

10/10 Excellent

"All of the above. "

[](https://expedia.co.uk/Baltimore-Hotels-Hampton-Inn-Baltimore-Bayview-Campus.h23830804.Hotel-Information)

![The Inn at Henderson's Wharf, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/38664fff_y.jpg)

### The Inn at Henderson's Wharf, an Ascend Collection Hotel

10/10 Excellent

"Never have a bad stay here. Rooms are always clean, staff is always friendly. Coffee machine is wonderful. Happy Hour was great each night. This is a must stay if in Fells Point!"

[](https://expedia.co.uk/Baltimore-Hotels-The-Inn-At-Hendersons-Wharf.h889993.Hotel-Information)

![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5_y.jpg)

### Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent

"Pretty clean and nice. Kids enjoyed the pool. Overall it was pretty good!"

[](https://expedia.co.uk/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information)

![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg)

### Best Western Plus Hotel & Conference Center

10/10 Excellent

"The room was clean, the variety of food for breakfast made hit the mark for our various appetites. The parking was sufficient. The staff was great! After checking out and on the road, I realized I left my medication in the fridge in the room. I called the front desk and the staff member was courteous and helpful. They held my medication until I was able to pick it up later that afternoon. Most importantly, they kept it refrigerated! That made me want to stay there whenever traveling and also recommend it to others. Thank you!"

[](https://expedia.co.uk/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information)

![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg)

### Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent

"Good Location and friendly staff....."

[](https://expedia.co.uk/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information)

## More cheap stays in Chestertown

![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Best Western Plus Hotel & Conference Center

5625 O'Donnell Street Baltimore MD

£79

14 Dec - 15 Dec

includes taxes & fees

7.6/10 Good! (1,002 reviews)

[](https://expedia.co.uk/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information)

![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Quality Inn & Suites Bel Air I-95 Exit 77A

2112a Emmorton Park Road Edgewood MD

£54

27 Nov - 28 Nov

includes taxes & fees

7.2/10 Good! (1,018 reviews)

[](https://expedia.co.uk/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information)

![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Fairfield Inn & Suites by Marriott White Marsh

8477 Cordon Way Baltimore MD

£80

10 Dec - 11 Dec

includes taxes & fees

8.4/10 Very Good! (1,003 reviews)

[](https://expedia.co.uk/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information)

![Americas Best Value Inn Edgewood](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Americas Best Value Inn Edgewood

1709 Edgewood Road Edgewood MD

£43

27 Nov - 28 Nov

includes taxes & fees

5.6/10 (1,001 reviews)

[](https://expedia.co.uk/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information)

![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hampton Inn & Suites Edgewood/Aberdeen-South

2110 Emmorton Park Rd Edgewood MD

£69

2 Dec - 3 Dec

includes taxes & fees

9.2/10 Wonderful! (1,007 reviews)

[](https://expedia.co.uk/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information)

![Comfort Inn & Suites Aberdeen near APG](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/0fca1b7b_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Comfort Inn & Suites Aberdeen near APG

980 Hospitality Way Aberdeen MD

£65

21 Dec - 22 Dec

includes taxes & fees

7.8/10 Good! (797 reviews)

[](https://expedia.co.uk/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.Hotel-Information)

## Find out more about Chestertown

### Top reasons to visit Chestertown

-   **Historic Charm:** Explore the picturesque streets adorned with colonial architecture, reflecting Chestertown's rich history.
-   **Outdoor Activities:** Enjoy a variety of outdoor pursuits, from boating at Tolchester Marina to leisurely strolls along scenic waterfronts.
-   **Beautiful Parks:** Relax in local parks and picnic areas, perfect for family gatherings amidst nature.
-   **Vibrant Community:** Experience the warm hospitality of Chestertown, with welcoming accommodations for all types of travellers.
-   **Scenic Beauty:** Revel in the stunning landscapes of the Eastern Shore, ideal for a relaxing getaway.

### Find great hotels near Chestertown

Discover a charming selection of hotels in Chestertown, Maryland, perfect for every traveller. Whether you're seeking pet-friendly accommodations, business-themed stays, or LGBTQIA welcoming environments, Chestertown offers a variety of options to suit your needs. With its picturesque surroundings and warm hospitality, you're sure to find the best Chestertown hotels that provide a memorable vacation experience.

-   **[Quality Inn & Suites Bel Air I-95 Exit 77A:](https://www.expedia.co.uk/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information)** Ideal for business travellers, Quality Inn & Suites Bel Air I-95 Exit 77A combines comfort with functionality. Located 13.0km from Chestertown, this hotel offers a range of services tailored to meet the needs of professionals on the go. Guests appreciate the well-equipped business centre, complimentary Wi-Fi, and meeting facilities. The hotel’s spacious rooms are designed for relaxation after a busy day, making it a perfect retreat for those looking to balance work and leisure.
-   **[Red Roof Inn Aberdeen:](https://www.expedia.co.uk/Aberdeen-Hotels-Red-Roof-Inn-Aberdeen.h12576.Hotel-Information)** Embracing inclusivity, Red Roof Inn Aberdeen is a welcoming haven for LGBTQIA travellers and their furry companions. Located 13.7km from Chestertown, this hotel is committed to providing a safe and friendly environment. It accommodates pets with specific policies in place, ensuring both human and animal guests feel at home. The property is known for its comfortable rooms and convenience, making it an ideal choice for those seeking a pet-friendly stay that celebrates diversity.
-   **[Americas Best Value Inn Edgewood:](https://www.expedia.co.uk/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information)** Situated 13.0km from Chestertown, Americas Best Value Inn Edgewood is a charming option for pet owners looking for affordable lodging. This hotel allows pets and offers a friendly atmosphere for both guests and their four-legged friends. With flexible pet policies and comfortable rooms, it caters to those who appreciate convenience without compromising on quality. Guests enjoy easy access to local attractions while feeling at home in this welcoming environment.

### Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of historical charm and outdoor adventures. Explore the picturesque streets lined with colonial architecture, or head to the nearby Tolchester Marina for a day of boating on the Chesapeake Bay. The Eastern Shore’s scenic beauty provides a perfect backdrop for family-friendly activities, making it an ideal destination for those seeking relaxation and friendly encounters. Discover the unique vibes of this charming town and its surrounding areas during your visit.

-   **[Worton:](https://www.expedia.co.uk/Worton-Hotels.d3000440948.Travel-Guide-Hotels)** Located a mere 2.5km from Chestertown, Worton offers a delightful escape for outdoor enthusiasts and nature lovers. The town boasts scenic landscapes, perfect for leisurely walks and picnics. Visitors flock here during spring and summer months for its vibrant recreational areas, including nearby beaches and marinas. Notable attractions include a national state park that invites exploration and adventure, making it an ideal spot for those wishing to soak in Maryland's natural beauty.
-   **[Georgetown:](https://www.expedia.co.uk/Georgetown-Hotels.d553248635975874069.Travel-Guide-Hotels)** Nestled within the vicinity of Chestertown, Georgetown is a charming village that attracts visitors with its outdoor experiences and romantic settings. Peak travel times occur during the warm summer months, when guests can enjoy various recreational activities. The village is home to a sports facility stadium and access to a national state park, both of which are perfect for those seeking an active holiday. The quaint atmosphere combined with adventurous pursuits makes Georgetown a lovely addition to your itinerary.
-   **[Tolchester Beach:](https://www.expedia.co.uk/Tolchester-Beach-Hotels.d553248635975848245.Travel-Guide-Hotels)** This picturesque village, located close to Chestertown, is a hidden gem for beach lovers and outdoor adventurers alike. Tolchester Beach sees a consistent flow of visitors, particularly in late spring and summer. The scenic boardwalk along the beach invites leisurely strolls, while the proximity to marinas and a national state park enhances its appeal. With its inviting atmosphere and beautiful landscapes, Tolchester Beach is perfect for a relaxing day by the water or an adventure-filled outing.

### Things to do in and around Chestertown

Chestertown, Maryland, offers a delightful blend of outdoor activities and scenic beauty, perfect for a relaxing holiday. Visitors can enjoy educational experiences, explore recreational areas, and stroll along the picturesque boardwalk. A highlight for families and friends is the picnic area, ideal for enjoying a leisurely meal amidst nature. Chestertown promises a charming getaway filled with enjoyable activities and beautiful landscapes.

**Shopping**

In Chestertown, you can enjoy quaint shops for unique gifts. If you're up for a drive, visit Queenstown Premium Outlets for a variety of brands, 10.6km away, or explore Westown, a family-friendly shopping centre, 14.9km away, offering a great mix of stores.

**Recreation**

Experience the energetic atmosphere at Ripken Stadium, only 13.7km from Chestertown, where you can enjoy various sporting events. Alternatively, Queenstown Harbor Golf Club and Queenstown Harbor Golf Links, both 10.6km away, offer stunning outdoor settings for a round of golf amidst beautiful landscapes.

**Adventure**

Explore the Emmorton Recreation & Tennis Center, 14.9km from Chestertown, for thrilling tennis matches and recreational activities. Experience the Annapolis Sailing School, 17.4km away, where you can enjoy sailing lessons amidst scenic waters. Alternatively, head to the Tose Family Tennis Center, also 17.4km distant, for more tennis excitement.

**Nightlife**

In Chestertown, the Garfield Center for the Arts at the Prince Theatre offers a vibrant cultural experience, while the nearby Church Hill Theatre and Everett Theatre provide additional entertainment options, all featuring a charming atmosphere perfect for families and couples seeking a delightful night out.

### Booking tips and Expedia advantages for Chestertown

To save money on your trip to Chestertown, consider visiting during the off-peak months of January to February or November, when accommodation rates are lower. Booking your stay on a Tuesday can also yield savings compared to weekends. Use Expedia’s search tool to find budget-friendly hotel options, and don't forget to check for military discounts. Combine your hotel with flights and activities for additional savings. For free activities, explore the charming town and its scenic waterfront. Planning your visit during these times can significantly enhance your budget while enjoying Chestertown's offerings.

-   **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Chestertown are January to February and November, where the prices are slightly lower. This is in comparison to June to July and October, where prices are slightly higher.
-   **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Chestertown is Tuesday. The most expensive day to stay in Chestertown is Saturday.
-   **Find cheap hotels on Expedia:** Utilise Expedia’s search tool to refine your preferences such as budget, desired location, and the type of hotel you favour. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
-   **Consider bundling your trip:** You can save money by combining your hotel stay in Chestertown with your flights and activities through an Expedia package.

### Find the best attractions in Chestertown

Chestertown offers a delightful blend of outdoor activities and scenic beauty, making it perfect for a beachside family holiday. Visitors can explore the charming historic district, relax in local parks, and enjoy the picturesque waterfront. For those keen on outdoor adventures, the area boasts beautiful beaches and urban parks, providing ample opportunities for relaxation and recreation amidst stunning surroundings.

-   **Washington College:** Nestled in the heart of Chestertown, Washington College boasts a rich history and vibrant campus life, offering a unique blend of academic excellence and cultural events. Stroll through its picturesque grounds and enjoy the charming architecture that reflects its storied past.
-   **Rolphs Wharf Marina:** For those seeking adventure, Rolphs Wharf Marina is a haven for outdoor enthusiasts. Engage in various water activities, relax by the beach, or simply soak in the stunning views of the Chester River, making it an ideal spot for a day of exploration.
-   **Historical Society of Kent County Maryland:** Immerse yourself in the local heritage at the Historical Society of Kent County Maryland. This museum offers fascinating exhibits that illuminate the region's history, culture, and traditions, providing a deeper understanding of Chestertown's past.

### Best time to go to Chestertown

The best time to visit Chestertown is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

| **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** |
| --- | --- | --- | --- | --- | --- |
| January | 34.2°F (1.2°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low |
| February | 36.9°F (2.7°C) | Light Rain | Mostly Sunny | Average | Slightly Low |
| March | 43.7°F (6.5°C) | Light Rain | Mostly Sunny | Average | Average |
| April | 54.3°F (12.4°C) | Light Rain | Mostly Sunny | Slightly High | Average |
| May | 63.7°F (17.6°C) | Light Rain | Mostly Sunny | Average | Average |
| June | 72.1°F (22.3°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High |
| July | 77.4°F (25.2°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High |
| August | 75.6°F (24.2°C) | Light Rain | Mostly Sunny | Average | Slightly High |
| September | 69.4°F (20.8°C) | Light Rain | Mostly Sunny | Average | Average |
| October | 59.2°F (15.1°C) | Light Rain | Mostly Sunny | Average | Average |
| November | 47.3°F (8.5°C) | Light Rain | Mostly Sunny | Slightly Low | Average |
| December | 40.1°F (4.5°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low |

### The nearest major airports for your trip to Chestertown

To reach Chestertown, Maryland, tourists can fly into several major airports. Washington, DC ([DCA](https://www.expedia.co.uk/Ronald-Reagan-Washington-National-Airport-Hotels.0-aDCA-0.Travel-Guide-Filter-Hotels) - Ronald Reagan Washington National) is situated 36.0km away, with luxurious hotels like [Salamander Washington DC](https://www.expedia.co.uk/Washington-Hotels-Salamander-Washington-DC.h1044257.Hotel-Information) and InterContinental Washington D.C. - The Wharf, both only 1.2km from the airport. Baltimore, MD ([BWI](https://www.expedia.co.uk/Baltimore-Washington-Intl-Thurgood-Marshall-Airport-Hotels.0-aBWI-0.Travel-Guide-Filter-Hotels) - Baltimore Washington International Thurgood Marshall) is closer at 31.2km, featuring exquisite options such as [Sagamore Pendry Baltimore](https://www.expedia.co.uk/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) and [The Ivy Hotel](https://www.expedia.co.uk/Baltimore-Hotels-The-Ivy-Hotel.h9343273.Hotel-Information). Alternatively, Baltimore, MD (MTN - Martin State) is 12.4km away, offering accommodations like [Canopy by Hilton Baltimore Harbor Point](https://www.expedia.co.uk/Baltimore-Hotels-Canopy-By-Hilton-Baltimore-Harbor-Point.h45976006.Hotel-Information) and [Hyatt Place Baltimore Inner Harbor](https://www.expedia.co.uk/Baltimore-Hotels-Hyatt-Place-Baltimore-Inner-Harbor.h8842065.Hotel-Information). Each airport provides convenient access to the respective hotels for a comfortable stay.

## Frequently asked questions

### What is the best area to stay in Chestertown?

> Great Oak Landing is the premier area to stay in Chestertown, Maryland, highly favoured by our travellers. Nestled along the picturesque Chester River, this serene neighbourhood offers stunning waterfront views and easy access to nature's beauty. Guests can enjoy leisurely strolls along the riverwalk or explore the nearby parks, making it a fantastic spot for outdoor enthusiasts.
> 
>   
> 
> For couples seeking a tranquil escape, Great Oak Landing provides a romantic backdrop for quality time together. Imagine sipping coffee on your private balcony while watching the sunrise over the water or enjoying a sunset picnic on the riverbank. The intimate setting is great for creating cherished memories.
> 
>   
> 
> Families will also appreciate the area, as it combines relaxation with family-friendly activities. The spacious rooms and proximity to local attractions mean there's something for everyone, from exploring the charming town centre to engaging in water sports on the Chester River.

### What are the best hotels in Chestertown that travellers recommend?

> The Lodge at Great Oak Landing is a charming getaway in Chestertown, rated 7.8 by guests. This hotel offers a picturesque setting with an onsite golf course, superb for those looking to enjoy a leisurely game amidst stunning natural surroundings. The attentive staff and inviting space create a lovely retreat for all visitors.

### What are the best family hotels in Chestertown?

> The Lodge at Great Oak Landing in Chestertown is a delightful option for families seeking a relaxing getaway. This charming property boasts a refreshing pool, great for kids to splash around and enjoy sunny days, along with a playground that guarantees endless fun for the little ones. Find more [child-friendly accommodations in Chestertown](https://www.expedia.co.uk/Chestertown-Hotels-Family-Friendly-Hotel.0-0-d7215-tFamilyFriendlyHotel.Travel-Guide-Filter-Hotels).

### What are the best budget hotels in Chestertown?

> For travellers seeking budget-friendly accommodations in Chestertown, the [Comfort Inn & Suites Chestertown](https://www.expedia.co.uk/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) stands out with an excellent review score of 8.6. This inviting hotel offers a range of family-friendly amenities, including a seasonal outdoor pool and complimentary breakfast, ensuring a delightful start to your day. Families will appreciate the child-friendly window design and the availability of cribs, making it a great choice for those traveling with little ones. Plus, the convenience of free WiFi and self-parking adds to the overall value.
> 
>   
> 
> Another excellent option is the Red Roof Inn & Suites Chestertown, which scores a solid 7.4 in guest reviews. This hotel also provides a friendly setting for families, featuring free cribs and a sofa bed that can accommodate larger groups. The free long-distance calls and in-room internet make it easy to stay connected during your travels. Located in the historical district, this property offers unique charm alongside practicality without breaking the bank.
> 
>   
> 
> For those interested in a slightly different experience, The Lodge at Great Oak Landing, with a review score of 7.8, caters well to couples and those looking for a scenic getaway. Nestled by the water, it features a shared outdoor pool and beachfront access, great for romantic strolls on the sand. Golf enthusiasts will also find delight in the on-site golf course, adding an adventurous twist to their stay. View all [budget hotels in Chestertown](https://www.expedia.co.uk/Chestertown-Hotels-Budget-Hotels.0-0-d7215-tBudgetHotels.Travel-Guide-Filter-Hotels).

### When is the best time to go to Chestertown?

> The most popular time to visit Chestertown is during the vibrant summer months, particularly July. With average temperatures reaching around 28°C, this is when the town truly comes alive with outdoor activities, festivals, and events. The warm weather invites visitors to enjoy the scenic waterfront, explore the charming streets filled with historic architecture, and take part in local celebrations.
> 
>   
> 
> As you plan your visit, bear in mind that the peak tourist season runs from June to August. This bustling time offers a plethora of activities, from boating on the Chester River to strolling through the lively farmers' market. The atmosphere is electric, with plenty of opportunities for outdoor dining, allowing you to savour local seafood while soaking up the sun. Engaging with the local community at various events can enhance your experience, making it a memorable adventure.
> 
>   
> 
> For those who prefer a quieter experience, consider visiting Chestertown in the shoulder season of late September or early October. The weather remains pleasant, with temperatures around 22°C, and you can enjoy the stunning autumn foliage without the summer crowds. It's an excellent time for leisurely walks along the river or visiting nearby wineries, where you can indulge in tastings amidst beautiful fall scenery.

### Can I cancel my hotel reservation on Expedia?

> Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Chestertown hotel for you.

### How can I save on a Chestertown hotel booking with Expedia?

> Members always get our best prices. Find our best Chestertown hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.

### How much is the nightly rate at a Chestertown hotel?

> Prices for hotels in Chestertown often vary, but you can find a great deal from £43 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)