Title: Hotels in Chester, MD - Best Chester Hotels from £64 - Fully Refundable Options - Expedia.co.uk

  

[Holiday Rentals in Chester](https://expedia.co.uk/Chester-Holiday-Rentals.d3000440455.Travel-Guide-HolidayRentals)[Chester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chester.d3000440455.Car-Hire-Guide)[Chester Holidays](https://expedia.co.uk/Chester.d3000440455.Holidays-City-Breaks)

![Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is  at least 3 miles long.](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Patricia Knorr

# Find hotels in Chester, MD from £64

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## Go beyond your typical stay in Chester

Pool

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&amenities=POOL)

Sea view

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&amenities=OCEAN_VIEW)

Apart­ment

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&lodging=APARTMENT)

Family friendly

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&travelerType=family_friendly)

Pet friendly

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&amenities=PETS)

Hot tub

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&amenities=HOT_TUB)

Cottage

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&lodging=COTTAGE)

Waterpark

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&amenities=WATER_PARK)

## Check prices for these dates

Tonight

[17 Oct - 18 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[18 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2025-10-18&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[24 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top 10 Chester hotels and places to stay

![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)

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

![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.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

(906)

"Nice Holiday Inn Express with great water views."

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

Michael

£92

includes taxes & fees

16 Nov - 17 Nov

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

![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/bdf87bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Place Kent Narrows & Marina

Grasonville

9.4/10

Exceptional

(640)

"Nice location and restaurants galore in area. "

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

David

£123

includes taxes & fees

26 Oct - 27 Oct

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

![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/5b1966a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Single Room, 1 King Bed | 1 bedroom, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kent Island Resort

Stevensville

9.2/10

Wonderful

(114)

"Great INN super nice staff"

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

Eric

£182

includes taxes & fees

19 Oct - 20 Oct

[](https://www.expedia.co.uk/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/67adefe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, dinner and brunch served](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/0684bd50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, dinner and brunch served](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/768e2886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Westin Annapolis

Annapolis

8.6/10

Excellent

(1006)

"Would stay there again very soon "

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

Robert

£152

includes taxes & fees

27 Oct - 28 Oct

[](https://www.expedia.co.uk/Annapolis-Hotels-The-Westin-Annapolis.h1678710.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)

![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/e17d8d11.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

(1005)

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

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

Roberta

£121

includes taxes & fees

26 Oct - 27 Oct

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

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/122348e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/7f9539e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/f531cd56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/7e58a966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott Annapolis

Annapolis

8.6/10

Excellent

(1001)

"The room was great, and the staff was great. "

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

Mario

£85

includes taxes & fees

17 Nov - 18 Nov

[](https://www.expedia.co.uk/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/c1b842f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/be7252cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/5c9aedf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Inns of Annapolis

Historic District

9.0/10

Wonderful

(1861)

"The hotel was absolutely clean and close to the shops and restaurants. "

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

Trudy

£114

includes taxes & fees

2 Nov - 3 Nov

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

![Premium bedding, pillow-top beds, in-room safe, individually furnished](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/23865424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/76e0b277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/ff58e28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/e600218e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn & Suites Annapolis

Annapolis

8.2/10

Very good

(1010)

"We had a nice stay. "

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

L Craig

£80

includes taxes & fees

2 Nov - 3 Nov

[](https://www.expedia.co.uk/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/w5759h3834x0y6-7304a3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/76f6e3e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/cfbb67fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Crowne Plaza Annapolis by IHG

Annapolis

8.8/10

Excellent

(1003)

"Good location"

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

William Charles Reinhart

£85

includes taxes & fees

2 Nov - 3 Nov

[](https://www.expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information)

![Hypo-allergenic bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/f7bcd5fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/9ddea0cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/6281ec00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/7f54b5f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Annapolis

Annapolis

8.2/10

Very good

(1010)

"I had a lovely stay."

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

Kalynn

£71

includes taxes & fees

16 Nov - 17 Nov

[](https://www.expedia.co.uk/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis.h1641168.Hotel-Information)

![1 bedroom, hypo-allergenic bedding, desk, blackout curtains](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/6ea498fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/19214323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/9e6dd0ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

9.0/10

Wonderful

(1016)

"Great place to stay Friendly staff secure rooms Thank you "

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

Shirley

£82

includes taxes & fees

2 Nov - 3 Nov

[](https://www.expedia.co.uk/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information)

![Garden](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/3952dad0.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/1000000/10000/3100/3040/5575a0f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DoubleTree by Hilton Hotel Annapolis

Annapolis

8.6/10

Excellent

(1018)

"Comfortable place to stay, nice shopping area close by. "

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

Roya

£90

includes taxes & fees

19 Oct - 20 Oct

[](https://www.expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information)

![Egyptian cotton sheets, premium bedding, pillow-top beds, desk](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/6846c015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/fbea7cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e7e5362c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonesta ES Suites Annapolis

Edgewater

8.8/10

Excellent

(919)

"Had a great stay."

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

Melvin

£69

includes taxes & fees

16 Nov - 17 Nov

[](https://www.expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information)

![Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed, Non Smoking | Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/6d79f12f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 2 Queen Beds, Non Smoking | Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/f68fafe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/af281015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Annapolis Waterfront Hotel, Autograph Collection

Historic District

8.8/10

Excellent

(871)

"Clean room. Friendly staff awesome location. "

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

Brent

£172

includes taxes & fees

9 Nov - 10 Nov

[](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information)

![Free daily self-service breakfast ](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/ac9f5b9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/cea7f239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pillow-top beds, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/08fc01db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SpringHill Suites by Marriott Annapolis

Annapolis

9.0/10

Wonderful

(1010)

"Clean room, Good breakfast and friendly staff."

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

Margaret C

£86

includes taxes & fees

16 Nov - 17 Nov

[](https://www.expedia.co.uk/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/335c1120.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room, 2 Double Beds, Non Smoking | Bathroom | Combined shower/bathtub, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/516c17a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Coffee service](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/bf93fe2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/8f46f567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Village Inn Annapolis MD

Annapolis

6.2/10

(504)

"The room was very nice, clean and quiet. Great location"

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

William

£70

includes taxes & fees

2 Nov - 3 Nov

[](https://www.expedia.co.uk/Annapolis-Hotels-Village-Inn.h530229.Hotel-Information)

![Front of property – evening/night](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/d2860230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/cca95561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/9f06834f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Chesapeake Bay Beach Club

Stevensville

9.4/10

Exceptional

(422)

"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "

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

Rery

£179

includes taxes & fees

2 Nov - 3 Nov

[](https://www.expedia.co.uk/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information)

![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/59ba3f76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed, Non Smoking (Whirlpool) | In-room safe, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/21b35d2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/d39579fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room amenity](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/9a55b500.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express & Suites Annapolis by IHG

Annapolis

8.2/10

Very good

(1002)

"Staff at front desk were incredibly friendly and helpful!"

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

Nina

£89

includes taxes & fees

16 Nov - 17 Nov

[](https://www.expedia.co.uk/Annapolis-Hotels-Holiday-Inn-Express-Suites-Annapolis.h20333.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/10000/900/846/237feb4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/e94a05fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/900/846/4033d0a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Graduate by Hilton Annapolis

Annapolis

9.4/10

Exceptional

(1011)

"Staff was outstanding!"

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

Fred

£131

includes taxes & fees

10 Nov - 11 Nov

[](https://www.expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information)

![Outdoor banquet area](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/w2877h1800x0y0-f772721c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/b30d5f43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Double Queen First Level - Dog Friendly | View from room](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/0c190249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/ee1a612d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Tilghman Island Inn

Tilghman

9.6/10

Exceptional

(114)

"Great staff and food!"

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

Natalie

£164

includes taxes & fees

2 Nov - 3 Nov

[](https://www.expedia.co.uk/Tilghman-Hotels-The-Tilghman-Island-Inn.h59854328.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=2025-11-01&endDate=2025-11-02&regionId=3000440455&adults=2&sort=RECOMMENDED&openPlayBack=true)

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

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

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## Stay near popular Chester attractions

[](https://www.expedia.co.uk/Chesapeake-Exploration-Center-Hotels.0-l553248621561879491-0.Travel-Guide-Filter-Hotels)

### Chesapeake Exploration Center

Learn about the events happening in Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.

[See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621561879491)

## Learn more about Chester

Chester awaits: its island views, sunny weather, golf and more!

[See all hotels in Chester](https://www.expedia.co.uk/Hotel-Search?startDate=2025-11-01&endDate=2025-11-02&adults=2&regionId=3000440455)

![](https://mediaim.expedia.com/destination/2/5fdecfa9ea611e8f8d02038dea5d1c0a.jpg?impolicy=fcrop&w=900&h=547&p=1&q=high)

Photo by Patricia Knorr

## Top Chester Hotel Reviews

![Sonesta ES Suites Annapolis](//images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg)

### Sonesta ES Suites Annapolis

10/10 Excellent

"Our night at your hotel was just fine! Room was clean. Supply toiletries, towels for the bath and kitchen were as expected, neat and plentiful. There was a creak in the bathroom door, but that is a nitpick. Coffee maker was easy to operate. Breakfast was as expected, with some delay when coffee carafe and food service trays were empty. I would go back."

[](https://expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information)

![Best Western Annapolis](//images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg)

### Best Western Annapolis

10/10 Excellent

"Clean room, nice staff and plenty of parking "

[](https://expedia.co.uk/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information)

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

### Historic Inns of Annapolis

10/10 Excellent

"The hotel was absolutely clean and close to the shops and restaurants. "

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

![Graduate by Hilton Annapolis](//images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg)

### Graduate by Hilton Annapolis

10/10 Excellent

"Staff was outstanding!"

[](https://expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information)

![Annapolis Waterfront Hotel, Autograph Collection](//images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg)

### Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Clean room. Friendly staff awesome location. "

[](https://expedia.co.uk/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information)

![St Michaels Inn](//images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg)

### St Michaels Inn

10/10 Excellent

"yes"

[](https://expedia.co.uk/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information)

![The Westin Annapolis](//images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg)

### The Westin Annapolis

10/10 Excellent

"excellent service for our Remodelers Advantage Conference. Food was delicious and service to the rooms for snacks was great as well"

[](https://expedia.co.uk/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information)

![Country Inn & Suites by Radisson, Annapolis, MD](//images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg)

### Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"Bed linens were very disappointing. Pillows, sheets and blanket were flimsy and cheap. "

[](https://expedia.co.uk/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information)

![DoubleTree by Hilton Hotel Annapolis](//images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg)

### DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"The staff were uniformly attentive and friendly."

[](https://expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information)

## More cheap stays in Chester

![Best Western Annapolis](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Best Western Annapolis

2520 Riva Rd, Annapolis, MD

£64

16 Nov - 17 Nov

includes taxes & fees

7.6/10 Good! (1,011 reviews)

[](https://expedia.co.uk/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information)

![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### St Michaels Inn

1228 S Talbot Street, St. Michaels, MD

£73

28 Oct - 29 Oct

includes taxes & fees

8/10 Very Good! (1,007 reviews)

[](https://expedia.co.uk/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information)

![Hampton Inn & Suites Annapolis](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/23865424_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hampton Inn & Suites Annapolis

124 Womack Dr, Annapolis, MD

£80

2 Nov - 3 Nov

includes taxes & fees

8/10 Very Good! (1,007 reviews)

[](https://expedia.co.uk/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information)

![Quality Inn](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/ead5e21d_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Quality Inn

101 Vfw Ave, Grasonville, MD

£79

16 Nov - 17 Nov

includes taxes & fees

7.8/10 Good! (840 reviews)

[](https://expedia.co.uk/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information)

![Candlewood Suites Annapolis by IHG](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/9088c5e1_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Candlewood Suites Annapolis by IHG

1 Womack Dr, Annapolis, MD

£75

16 Nov - 17 Nov

includes taxes & fees

8.8/10 Excellent! (142 reviews)

[](https://expedia.co.uk/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information)

![Quality Inn](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/fbc96e63_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Quality Inn

8523 Ocean Gtwy, Easton, MD

£70

30 Oct - 31 Oct

includes taxes & fees

7.6/10 Good! (796 reviews)

[](https://expedia.co.uk/Easton-Hotels-Quality-Inn.h11364.Hotel-Information)

## Frequently asked questions

### Where can I find the best nightlife in Chester?

> Chester is a charming area with a laid-back atmosphere, but when it comes to nightlife, options are somewhat limited.
> 
>   
> 
> However, nearby Annapolis, just a short drive away, boasts a vibrant nightlife scene that's well worth the visit. In Annapolis, the historic downtown area features bustling bars and live music venues along West Street, where you can enjoy everything from casual pubs to upscale lounges.
> 
>   
> 
> For those who enjoy a lively waterfront experience, the area around Ego Alley is superb for sipping cocktails while watching boats glide by. If you're searching for a relaxed evening, consider heading to the local breweries or wine bars that often host events and tastings.

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

> You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chester.

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

> With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Chester hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings.

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

> Prices for hotels in Chester often vary, but you can find a great deal from £64 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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-   [Luxury Hotels in Northern Chesapeake Bay](https://www.expedia.co.uk/Northern-Chesapeake-Bay-Hotels-Luxury-Hotel.0-0-d6051456-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Preferred Hotels in Northern Chesapeake Bay](https://www.expedia.co.uk/Northern-Chesapeake-Bay-Hotels-Preferred.0-0-d6051456--bPreferred.Travel-Guide-Filter-Hotels)
-   [Motels in Northern Chesapeake Bay](https://www.expedia.co.uk/Northern-Chesapeake-Bay-Motels.d6051456-aaMotels.Travel-Guide-Accommodation)
-   [Gay-Friendly Hotels in Oyster Harbor](https://www.expedia.co.uk/Oyster-Harbor-Annapolis-Hotels-Gay-Friendly-Hotel.0-n553248635976482330-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Marriott Hotels & Resorts in Queenstown](https://www.expedia.co.uk/Queenstown-Hotels-Marriott-Hotels-Resorts.0-0-d56094--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels)
-   [Queenstown Hotels](https://www.expedia.co.uk/Queenstown-Hotels.d56094.Travel-Guide-Hotels)
-   [Rock Hall Hotels](https://www.expedia.co.uk/Rock-Hall-Hotels.d177447.Travel-Guide-Hotels)
-   [Selby-On-The-Bay Hotels](https://www.expedia.co.uk/Selby-On-The-Bay-Hotels.d553248634999271692.Travel-Guide-Hotels)
-   [Severna Park Hotels](https://www.expedia.co.uk/Severna-Park-Hotels.d156680.Travel-Guide-Hotels)
-   [Shady Side Hotels](https://www.expedia.co.uk/Shady-Side-Hotels.d6264943.Travel-Guide-Hotels)
-   [Sherwood Hotels](https://www.expedia.co.uk/Sherwood-Hotels.d6034722.Travel-Guide-Hotels)
-   [St. Michaels Hotels](https://www.expedia.co.uk/St-Michaels-Hotels.d5940.Travel-Guide-Hotels)
-   [Stevensville Hotels](https://www.expedia.co.uk/Stevensville-Hotels.d162393.Travel-Guide-Hotels)
-   [Wittman Hotels](https://www.expedia.co.uk/Wittman-Hotels.d3000440946.Travel-Guide-Hotels)
-   [Wye Mills Hotels](https://www.expedia.co.uk/Wye-Mills-Hotels.d6359185.Travel-Guide-Hotels)

-   [Flights to Annapolis](https://www.expedia.co.uk/Cheap-Flights-To-Annapolis.d6034082.Travel-Guide-Flights)
-   [Flights to Kent Island](https://www.expedia.co.uk/Cheap-Flights-To-Kent-Island.d553248635077608788.Travel-Guide-Flights)
-   [Flights to Northern Chesapeake Bay](https://www.expedia.co.uk/Cheap-Flights-To-Northern-Chesapeake-Bay.d6051456.Travel-Guide-Flights)
-   [Flights to Maryland](https://www.expedia.co.uk/Destinations-In-Maryland.d222.Flight-Destinations)
-   [Flights from Stevensville](https://www.expedia.co.uk/lp/flights/162393/flights-from-stevensville)
-   [Flights from Kent Island](https://www.expedia.co.uk/lp/flights/553248635077608788/flights-from-kent-island)
-   [Flights from Queenstown](https://www.expedia.co.uk/lp/flights/56094/flights-from-queenstown)
-   [Flights from Annapolis](https://www.expedia.co.uk/lp/flights/6034082/flights-from-annapolis)
-   [Flights from Northern Chesapeake Bay](https://www.expedia.co.uk/lp/flights/6051456/flights-from-northern-chesapeake-bay)

-   [Annapolis Holidays](https://www.expedia.co.uk/Annapolis.d6034082.Holidays-City-Breaks)
-   [Visit Gibson Island](https://www.expedia.co.uk/Gibson-Island.dx3000347885)
-   [Hammond-Harwood House](https://www.expedia.co.uk/Hammond-Harwood-House-Historic-District.d6077396.Attraction)
-   [Visit Kent Island](https://www.expedia.co.uk/Kent-Island.dx553248635077608788)
-   [Maryland Holidays](https://www.expedia.co.uk/Maryland.d222.Holidays-City-Breaks)
-   [Visit Maryland](https://www.expedia.co.uk/Maryland.dx222)
-   [U.s. Naval Academy](https://www.expedia.co.uk/US-Naval-Academy-Annapolis.d6077390.Attraction)
-   [Adventure Holiday Packages Gibson Island](https://www.expedia.co.uk/lp/theme-holidays/adventure-holidays/3000347885/Gibson-Island)
-   [All inclusive Holiday Packages Gibson Island](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/3000347885/Gibson-Island)

-   [Amigo Autos Rental Cars in Kent Island](https://www.expedia.co.uk/Amigo-Autos-Car-Rentals-In-Kent-Island.d553248635077608788-c1128.Car-Rental-Guide-Suppliers)
-   [Car hire Annapolis](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Annapolis.d6034082.Car-Hire-Guide)
-   [Car hire near Kent Island](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Kent-Island.d553248635077608788.Car-Hire-Guide)
-   [Car hire Queenstown](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Queenstown.d56094.Car-Hire-Guide)
-   [Express Travel Group Rental Cars in Northern Chesapeake Bay](https://www.expedia.co.uk/Express-Travel-Group-Car-Rentals-In-Northern-Chesapeake-Bay.d6051456-c1124.Car-Rental-Guide-Suppliers)
-   [Firefly Portugal Rental Cars in Kent Island](https://www.expedia.co.uk/Firefly-Portugal-Car-Rentals-In-Kent-Island.d553248635077608788-c1071.Car-Rental-Guide-Suppliers)
-   [Hertz Rental Cars in Maryland](https://www.expedia.co.uk/Hertz-Destinations-In-Maryland.d222-c40.Car-Rental-Destination-Suppliers)
-   [Mini Car Hire in Gibson Island](https://www.expedia.co.uk/Mini-Car-Rentals-In-Gibson-Island.d3000347885-tMini.Car-Rental-Guide-Class)
-   [Oryx Rent A Car Rental Cars in Northern Chesapeake Bay](https://www.expedia.co.uk/ORYX-Rent-A-Car-Car-Rentals-In-Northern-Chesapeake-Bay.d6051456-c1059.Car-Rental-Guide-Suppliers)
-   [Orlando Rental Cars in Gibson Island](https://www.expedia.co.uk/Orlando-Car-Rentals-In-Gibson-Island.d3000347885-c1047.Car-Rental-Guide-Suppliers)
-   [Suv Car Hire in Gibson Island](https://www.expedia.co.uk/SUV-Car-Rentals-In-Gibson-Island.d3000347885-tSUV.Car-Rental-Guide-Class)
-   [United Rental Cars in Kent Island](https://www.expedia.co.uk/United-Car-Rentals-In-Kent-Island.d553248635077608788-c1088.Car-Rental-Guide-Suppliers)

-   [Annapolis Holiday Rentals](https://www.expedia.co.uk/Annapolis-Holiday-Rentals.d6034082.Travel-Guide-HolidayRentals)
-   [Kent Island Holiday Rentals](https://www.expedia.co.uk/Kent-Island-Holiday-Rentals.d553248635077608788.Travel-Guide-HolidayRentals)

-   [Things to do in Maryland](https://www.expedia.co.uk/Things-To-Do-In-Maryland.d222.Travel-Guide-Activities)

-   [Book Hotels in Chester on Expedia.com](https://www.expedia.com/Chester-Hotels.d3000440455.Travel-Guide-Hotels)

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