Title: Holiday Rentals Chestertown from £211: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

[Chestertown Travel Guide](https://expedia.co.uk/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.co.uk/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[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/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[17 Apr - 19 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[26 Jun - 28 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[24 Jul - 26 Jul](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chestertown holiday rentals

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/w1322h734x2y1-d973a563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/5cb9165d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/92366292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### First Floor Studio Apartment in Historic Chestertown

[](https://www.expedia.co.uk/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

Chestertown

9.6/10

Exceptional

(108 reviews)

"Every thing was great"

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

lesia k.

£123

includes taxes & fees

6 Apr - 7 Apr

[](https://www.expedia.co.uk/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w1024h677x0y0-664bab42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w876h683x74y0-d9537acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w584h683x220y0-d805a755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w509h683x257y0-37962ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Guest Suite for up to 2 in a Victorian on the Chester River

[](https://www.expedia.co.uk/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information)

Millington

9.6/10

Exceptional

(20 reviews)

"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."

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

Cynthia C.

£98

includes taxes & fees

14 Apr - 15 Apr

[](https://www.expedia.co.uk/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/w1014h600x10y12-4e8a8c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/w1024h592x0y17-9d1e8161.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/598d88e9_edited_b6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/819180d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 18th Cent. Charm in Historic Downtown Annapolis

[](https://www.expedia.co.uk/Annapolis-Hotels-18th-Cent-Charm-In-Historic-Downtown-Annapolis.h92564827.Hotel-Information)

Historic District

9.0/10

Wonderful

(14 reviews)

"Great experience"

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

David P.

£258

includes taxes & fees

2 Apr - 3 Apr

[](https://www.expedia.co.uk/Annapolis-Hotels-18th-Cent-Charm-In-Historic-Downtown-Annapolis.h92564827.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/2a64ee56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/737f2153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table football](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/44a64359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/30ebd57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 2 bedroom duplex located conveniently near Route 50 East and West. 

[](https://www.expedia.co.uk/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

Grasonville

9.6/10

Exceptional

(12 reviews)

"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "

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

Joe C.

£319

includes taxes & fees

6 Apr - 7 Apr

[](https://www.expedia.co.uk/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/fc34c762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/7e2b4765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/081c863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/c9b926ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2br home w/ parking in downtown Annapolis

[](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information)

Historic District

10/10

Exceptional

(75 reviews)

"Welcoming host, great location and easy parking "

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

Chris B.

£280

includes taxes & fees

2 Apr - 3 Apr

[](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/86c67d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/cf034cb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/76b495fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/02f199f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amazing Modern house with a full kitchen and parking 

[](https://www.expedia.co.uk/Smyrna-Hotels-Amazing-Modern-House-With-A-Full-Kitchen-And-Parking.h101539294.Hotel-Information)

Smyrna

9.2/10

Wonderful

(10 reviews)

"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "

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

Laurie S.

£212

includes taxes & fees

7 Apr - 8 Apr

[](https://www.expedia.co.uk/Smyrna-Hotels-Amazing-Modern-House-With-A-Full-Kitchen-And-Parking.h101539294.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/e5c30638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/a70d4b32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/86c425c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/3a482076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large 2 bedroom house with private parking in a nice neighborhood

[](https://www.expedia.co.uk/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

Arnold

9.4/10

Exceptional

(37 reviews)

"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "

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

Traci L.

£247

includes taxes & fees

5 Apr - 6 Apr

[](https://www.expedia.co.uk/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/1f4387ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/6a6e65f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/226d6f82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, offices](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/7fa2b473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hidden Fells Point Gem / Private Courtyard Patio

[](https://www.expedia.co.uk/Baltimore-Hotels-At-Fells-Point-Courtyard-Your-Historically-Restored-Apartment.h19008016.Hotel-Information)

Fells Point

9.6/10

Exceptional

(94 reviews)

"Awesome place, great location"

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

Mark M.

£158

includes taxes & fees

5 Apr - 6 Apr

[](https://www.expedia.co.uk/Baltimore-Hotels-At-Fells-Point-Courtyard-Your-Historically-Restored-Apartment.h19008016.Hotel-Information)

![Smart TV, printers](https://images.trvl-media.com/lodging/125000000/124570000/124564400/124564327/4e1114bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/125000000/124570000/124564400/124564327/9a6a354d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124570000/124564400/124564327/9169d391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124570000/124564400/124564327/be38f55e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Boho Oasis 2 Bed 1 Bath home in Baltimore City!

[](https://www.expedia.co.uk/Baltimore-Hotels-Boho-Oasis-2-Bed-1-Bath-Home-In-Baltimore-City.h124564327.Hotel-Information)

Berea

9.6/10

Exceptional

(5 reviews)

"House kept very clean and neighborhood was really quiet at night! Will be staying again."

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

Pai’Syn

£201

includes taxes & fees

3 Apr - 4 Apr

[](https://www.expedia.co.uk/Baltimore-Hotels-Boho-Oasis-2-Bed-1-Bath-Home-In-Baltimore-City.h124564327.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/a71c8e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/7d796cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/c53ddff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/w1024h678x0y5-f3e384c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Coastal/Country Home w/3 Acres & Sauna!

[](https://www.expedia.co.uk/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

Stevensville

9.6/10

Exceptional

(35 reviews)

"Great stay, would do it again."

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

Brandon D.

£211

includes taxes & fees

8 Apr - 9 Apr

[](https://www.expedia.co.uk/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/05f7fb5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/7f5de9e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/f65b9e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/a673c6f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom house in Aberdeen with WiFi and AC

[](https://www.expedia.co.uk/Aberdeen-Hotels-Charming-2-Bedroom-House-In-Aberdeen-With-WiFi-And-AC.h111819612.Hotel-Information)

Aberdeen

7.6/10

Good

(13 reviews)

"Met our needs. Great stay."

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

Robert C.

£73

includes taxes & fees

5 Apr - 6 Apr

[](https://www.expedia.co.uk/Aberdeen-Hotels-Charming-2-Bedroom-House-In-Aberdeen-With-WiFi-And-AC.h111819612.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/7d6d0051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/7a413e7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/4c5f6f69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/141e2e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### High Tide Haven Suite

[](https://www.expedia.co.uk/Still-Pond-Hotels-High-Tide-Haven-Suite.h120248155.Hotel-Information)

Kent County

£155

includes taxes & fees

2 Apr - 3 Apr

[](https://www.expedia.co.uk/Still-Pond-Hotels-High-Tide-Haven-Suite.h120248155.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/a2c7c68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/8ae0a25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/21befbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/4cfce214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bayside Cottage steps from Rock Hall Harbor

[](https://www.expedia.co.uk/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information)

Rock Hall

10/10

Exceptional

(2 reviews)

"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"

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

Dorothy R.

£268

includes taxes & fees

20 Apr - 21 Apr

[](https://www.expedia.co.uk/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/b1ed4047.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/66cb9c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/cc9a4892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/139d479a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

[](https://www.expedia.co.uk/Pasadena-Hotels-FLOHOM-14-Luxury-Houseboat-With-Chesapeake-Bay-Panoramic-Views.h118717298.Hotel-Information)

Pasadena

£323

includes taxes & fees

5 Apr - 6 Apr

[](https://www.expedia.co.uk/Pasadena-Hotels-FLOHOM-14-Luxury-Houseboat-With-Chesapeake-Bay-Panoramic-Views.h118717298.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/1aa587de_edited_b1ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h908x3y2-e4e5546a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1514h908x8y2-08d635bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h906x3y0-7a94439d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Row Home | Hot Tub - 1 Block from Gate 1!

[](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Row-Home-Hot-Tub-1-Block-From-Gate-1.h117588789.Hotel-Information)

Historic District

10/10

Exceptional

(5 reviews)

"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "

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

Tracie B.

£535

includes taxes & fees

6 Apr - 7 Apr

[](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Row-Home-Hot-Tub-1-Block-From-Gate-1.h117588789.Hotel-Information)

![Oven, stovetop](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/009658d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/f5323c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/f21ef3f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/1e2f03eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 40' Bristol sailboat with spectacular views

[](https://www.expedia.co.uk/Stevensville-Hotels-40-Bristol-Sailboat-With-Spectacular-Views.h120855751.Hotel-Information)

Stevensville

£326

includes taxes & fees

5 Apr - 6 Apr

[](https://www.expedia.co.uk/Stevensville-Hotels-40-Bristol-Sailboat-With-Spectacular-Views.h120855751.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/57f188cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/12356e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relax on Kent Island in a 4 Bedroom Home w/Waterview!

[](https://www.expedia.co.uk/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

Stevensville

9.8/10

Exceptional

(43 reviews)

"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"

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

Supriya V.

£221

includes taxes & fees

5 Apr - 6 Apr

[](https://www.expedia.co.uk/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/01162ab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/0cd3925a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/3d8089a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/e26e59da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

[](https://www.expedia.co.uk/Havre-De-Grace-Hotels-Cozy-2-Bedroom-Apartment-With-WiFi.h113298347.Hotel-Information)

Havre de Grace

10/10

Exceptional

(5 reviews)

"It is a warm and welcoming little home away from home. We will be back!"

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

Brittany C.

£162

includes taxes & fees

6 Apr - 7 Apr

[](https://www.expedia.co.uk/Havre-De-Grace-Hotels-Cozy-2-Bedroom-Apartment-With-WiFi.h113298347.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-479799f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-414422dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/673d3dea_edited_40cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-e0efb6c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Grandma’s Cottage will wrap around you like a warm hug

[](https://www.expedia.co.uk/Betterton-Hotels-Grandmas-Cottage-Will-Wrap-Around-You-Like-A-Warm-Hug.h113586648.Hotel-Information)

Betterton

£316

includes taxes & fees

9 Apr - 10 Apr

[](https://www.expedia.co.uk/Betterton-Hotels-Grandmas-Cottage-Will-Wrap-Around-You-Like-A-Warm-Hug.h113586648.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/b4e88275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/b0be7e2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/ee75c514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/5a5ec3f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

[](https://www.expedia.co.uk/Rock-Hall-Hotels-Walk-To-Everything-Rock-Hall-From-This-1st-Floor-Apartment-Sleeps-4.h104005223.Hotel-Information)

Rock Hall

10/10

Exceptional

(18 reviews)

"Close to Main Street. Very nice and spacious accommodations."

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

Michael D.

£216

includes taxes & fees

2 Apr - 3 Apr

[](https://www.expedia.co.uk/Rock-Hall-Hotels-Walk-To-Everything-Rock-Hall-From-This-1st-Floor-Apartment-Sleeps-4.h104005223.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=2026-04-15&endDate=2026-04-16&regionId=7215&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find holiday rentals that suit your style

Private holiday homes

[](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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=VACATION_HOME)

Cottages

[](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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=COTTAGE)

Apartments

[](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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=APARTMENT)

Condos

[](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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=CONDO)

Houseboats

[](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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=HOUSE_BOAT)

Cabins

[](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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=CABIN)

Residences

[](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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=RESIDENCE)

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## Top Chestertown Hotel Reviews

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg)

### Historic Inns of Annapolis

10/10 Excellent

"The parking valet was wonderful- so easy to park and also gave us recommendations of where to eat! Front desk personnel were also lovely. "

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

6/10 Okay

"Breakfast had plenty of choices for the family. The pool was supposed to be heated and it was not the majority of the days, with ceiling tiles falling down."

[](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/1000000/440000/433700/433663/6e9faa08_y.jpg)

### Hilton Garden Inn Baltimore/White Marsh

8/10 Good

"Breakfast, was delicious."

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

![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/40d24dc0_y.jpg)

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

2/10 Terrible

"Hotel is nasty straight up hood"

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

![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/5d79a398_y.jpg)

### Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent

"It was great!!! I would absolutely stay there again. Clean, friendly staff, comfy, quiet…"

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

![Home2 Suites by Hilton Baltimore/White Marsh](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/e611db61_y.jpg)

### Home2 Suites by Hilton Baltimore/White Marsh

8/10 Good

"Breakfast was nice"

[](https://expedia.co.uk/Baltimore-Hotels-Home2-Suites-By-Hilton-BaltimoreWhite-Marsh.h5991951.Hotel-Information)

![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda_y.jpg)

### Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Clean"

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

![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/c6a165a6_y.jpg)

### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good

"My Family and I enjoyed our stay here as well as the variety of breakfast options. Fell short of giving it an excellent review because we were initially given a room that seem to have mould on the bathroom ceiling, however, our room was changed once we complained and the new room was very clean. Will definitely recommend a stay here."

[](https://expedia.co.uk/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information)

![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/2b57d3ba_y.jpg)

### Hampton Inn Baltimore/Glen Burnie

10/10 Excellent

"A house problem means a one night local area stay. No issues with registration, good rate and clean room."

[](https://expedia.co.uk/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information)

## Find out more about Chestertown

**Everything you need to know about** **Chestertown** **holiday rentals**

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Chestertown holiday rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestertown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Chestertown holiday rentals we have selected for you start as low as £211 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Chestertown rentals**

At Expedia, we put the best Chestertown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

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- [South Wales Holiday Rentals ](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals)
- [North Wales Holiday Rentals ](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals)
- [London Holiday Rentals ](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals)
- [York Holiday Rentals ](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals)
- [Blackpool Holiday Rentals ](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals)
- [Isle of Wight Holiday Rentals ](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations)
- [Scarborough Holiday Rentals ](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals)
- [Edinburgh Holiday Rentals ](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals)
- [Bath Holiday Rentals ](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals)
- [Bournemouth Holiday Rentals ](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals)
- [England Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations)
- [Scotland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations)
- [Cornwall Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations)
- [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations)
- [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations)

## Frequently asked questions

### Are there holiday rentals in Chestertown?

### What are some of the best holiday rentals that Chestertown has to offer?

### How many holiday rentals are there in Chestertown?

### What can I see and do in Chestertown?

### What are holiday rentals like in Chestertown?

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