Title: Book The Best Hotels in Chester, MD for 2026 from CA $115 - Fully Refundable Options - Expedia.ca

[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d3000440455.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d3000440455.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d3000440455.Destination-Travel-Guides)

![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 CA $115

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## Go beyond your typical stay in Chester

Spa

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-23&d1=2025-12-23&endDate=2025-12-25&d2=2025-12-25&amenities=SPA_ON_SITE)

Resort

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-23&d1=2025-12-23&endDate=2025-12-25&d2=2025-12-25&lodging=HOTEL_RESORT)

Cabin

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-23&d1=2025-12-23&endDate=2025-12-25&d2=2025-12-25&lodging=CABIN)

Apart hotel

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-23&d1=2025-12-23&endDate=2025-12-25&d2=2025-12-25&lodging=APART_HOTEL)

Ryokan

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-23&d1=2025-12-23&endDate=2025-12-25&d2=2025-12-25&lodging=RYOKAN)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-23&d1=2025-12-23&endDate=2025-12-25&d2=2025-12-25&travelerType=family_friendly)

Farm

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-23&d1=2025-12-23&endDate=2025-12-25&d2=2025-12-25&lodging=AGRITOURISM)

Castle

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-23&d1=2025-12-23&endDate=2025-12-25&d2=2025-12-25&lodging=CASTLE)

House­boat

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-23&d1=2025-12-23&endDate=2025-12-25&d2=2025-12-25&lodging=HOUSE_BOAT)

Capsule hotel

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-23&d1=2025-12-23&endDate=2025-12-25&d2=2025-12-25&lodging=CAPSULE_HOTEL)

Ocean view

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-23&d1=2025-12-23&endDate=2025-12-25&d2=2025-12-25&amenities=OCEAN_VIEW)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2025-12-23&d1=2025-12-23&endDate=2025-12-25&d2=2025-12-25&amenities=PETS)

## Check prices for these dates

Tonight

[Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-09&endDate=2025-12-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-10&endDate=2025-12-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester hotels

![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](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/6b94b388.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

(930)

"the cleanliness of the rooms and hotel is awesome"

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

Leniya

Traveling with partner

CA $120

CA $133 total

includes taxes & fees

Jan 3 - Jan 4, 2026

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

![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/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)

### Hilton Garden Inn Kent Island Marina

Grasonville

9.0/10

Wonderful

(1001)

"The room was large and clean"

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

Tom

CA $143

CA $159 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.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)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/d4b92367.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)

### DoubleTree by Hilton Hotel Annapolis

Annapolis

8.6/10

Excellent

(1014)

"Great Hotel, Amazing location, very clean, everyone is friendly and helpful."

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

Tatiana

CA $106

CA $120 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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/e60ed5ff.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

9.6/10

Exceptional

(674)

"Our room was very clean, spacious and comfy."

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

Angela

Traveling with partner

CA $160

CA $178 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.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)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/04365757.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

(1000)

"The rooms were clean, comfortable and spacious."

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

Bridgett

Traveling for leisure

CA $213

CA $243 total

includes taxes & fees

Dec 24 - Dec 25

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

![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)

![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/29901fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Kent Island Resort

Stevensville

9.2/10

Wonderful

(128)

"It \[inn\] is located right on the water in a beautiful setting."

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

Eric

Traveling for leisure

CA $176

CA $244 total

includes taxes & fees

Dec 11 - Dec 12

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

![Room, 2 Queen Beds, Balcony](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/fb8e8cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, pillowtop 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)

![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/f68fafe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Annapolis Waterfront Hotel, Autograph Collection

Historic District

8.8/10

Excellent

(881)

"clean and close to everything"

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

Kelly

CA $246

CA $280 total

includes taxes & fees

Dec 15 - Dec 16

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

![Premium bedding, pillowtop 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)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/a336329e.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

(1003)

"Our room was very spacious, bedroom, living,kitchen with all the appliances that we needed."

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

aldo

Traveling with family

CA $125

CA $142 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.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)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/7e58a966.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)

### Courtyard by Marriott Annapolis

Annapolis

8.6/10

Excellent

(1000)

"Room is clean and spacious."

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

Lesley

Traveling for leisure

CA $134

CA $153 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.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

(1007)

"Very nice clean and newer room finishes."

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

Florbela

Traveling for leisure

CA $134

CA $153 total

includes taxes & fees

Dec 25 - Dec 26

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

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

![Lobby](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802.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)

![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)

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

Annapolis

9.0/10

Wonderful

(1000)

"room was clean and comfortable"

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

William

Traveling for leisure

CA $120

CA $137 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Hypo-allergenic bedding, down comforters, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/f7bcd5fc.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)

![Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/6281ec00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/57bd9cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Annapolis

Annapolis

8.2/10

Very good

(1000)

"I liked the spacious room and Jacuzzi."

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

Andre

CA $105

CA $120 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis.h1641168.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/be7252cc.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)

![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

(1907)

"the location was perfect for exploring downtown Annapolis!"

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

Christine

Traveling for leisure

[](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.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)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/5f8f1383.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, 1 King Bed, Non Smoking (Whirlpool)](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/21b35d2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express & Suites Annapolis by IHG

Annapolis

8.2/10

Very good

(1000)

"Clean room and friendly staff!"

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

Silvia

Traveling with partner

CA $111

CA $126 total

includes taxes & fees

Dec 20 - Dec 21

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

![Suite, 1 Bedroom, Terrace | Living area](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/8ee1610f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 2 Queen Beds, Accessible (Hearing)](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/aeb43618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/21c4fc7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Annapolis Downtown

Annapolis

8.6/10

Excellent

(1004)

"This hotel was fine for one night and in a desirable location in downtown Annapolis"

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

Brian

Traveling for leisure

CA $110

CA $125 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.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)

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

![Ballroom](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/b42a3a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Chesapeake Bay Beach Club

Stevensville

9.4/10

Exceptional

(429)

"Lovely outside areas to relax in like the gardens and fire pits."

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

Tamara

Traveling with partner

CA $255

CA $318 total

includes taxes & fees

Dec 14 - Dec 15

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

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

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079.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

(962)

"the room was nice and clean"

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

Tom

CA $126

CA $143 total

includes taxes & fees

Dec 29 - Dec 30

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

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

![Pillowtop 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)

![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/cea7f239.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)

### SpringHill Suites by Marriott Annapolis

Annapolis

9.0/10

Wonderful

(1000)

"Very clean hotel and convenient hotel location."

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

Tony

Traveling for leisure

CA $140

CA $159 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.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)

![Boating](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/b187b396.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)

![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)

### The Tilghman Island Inn

Tilghman

9.6/10

Exceptional

(120)

"Beautiful location on the water."

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

gwen

Traveling for leisure

CA $277

CA $305 total

includes taxes & fees

Dec 11 - Dec 12

[](https://www.expedia.ca/Tilghman-Hotels-The-Tilghman-Island-Inn.h59854328.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)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/e94a05fd.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/ca081b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Graduate by Hilton Annapolis

Annapolis

9.4/10

Exceptional

(1002)

"Nice big rooms, comfortable beds."

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

Margaret

CA $194

CA $221 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.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.ca/Hotel-Search?startDate=2025-12-23&endDate=2025-12-24&regionId=3000440455&adults=2&sort=RECOMMENDED&openPlayBack=true)

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

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## Learn more about Chester

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

[See all hotels in Chester](https://www.expedia.ca/Hotel-Search?startDate=2025-12-23&endDate=2025-12-24&adults=2&regionId=3000440455)

![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=900&h=547&p=1&q=high)

Photo by Patricia Knorr

### Stay near popular Chester attractions

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

#### Chesapeake Exploration Center

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

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

## More cheap stays in Chester

![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

CA $146

CA $161 total

Dec 17 - Dec 18

includes taxes & fees

8/10 Very Good! (1,001 reviews)

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

![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

CA $101

CA $115 total

Dec 19 - Dec 20

includes taxes & fees

7.6/10 Good! (1,001 reviews)

[](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.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

CA $125

CA $142 total

Dec 17 - Dec 18

includes taxes & fees

8/10 Very Good! (1,000 reviews)

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

![Candlewood Suites Annapolis by IHG](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/f27fb62d_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Candlewood Suites Annapolis by IHG

1 Womack Dr Annapolis MD

CA $116

CA $133 total

Dec 14 - Dec 15

includes taxes & fees

8.8/10 Excellent! (176 reviews)

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

![Best Western Kent Narrows Inn](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3968d160_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

CA $115

CA $128 total

Dec 30 - Dec 31

includes taxes & fees

8/10 Very Good! (1,002 reviews)

[](https://expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.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

CA $112

CA $123 total

Dec 28 - Dec 29

includes taxes & fees

7.6/10 Good! (824 reviews)

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

## Hotels in Chester with star-rating

![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg)

5 Star Hotels

3 properties

[](https://expedia.ca/5Star-Chester-Hotels.s50-0-d3000440455.Travel-Guide-Filter-Hotels)

![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg)

4 Star Hotels

6 properties

[](https://expedia.ca/4Star-Chester-Hotels.s40-0-d3000440455.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg)

3 Star Hotels

74 properties

[](https://expedia.ca/3Star-Chester-Hotels.s30-0-d3000440455.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg)

2 Star Hotels

80 properties

[](https://expedia.ca/2Star-Chester-Hotels.s20-0-d3000440455.Travel-Guide-Filter-Hotels)

## Recent reviews of Chester hotels

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

### DoubleTree by Hilton Hotel Annapolis

5/5 Excellent

"Clean upscale rooom..bed was amazing "

A verified traveller stayed at DoubleTree by Hilton Hotel Annapolis

Posted 13 hours ago

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

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

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

5/5 Excellent

"Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet."

A verified traveller stayed at Country Inn & Suites by Radisson, Annapolis, MD

Posted 2 days ago

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

![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg)

### Crowne Plaza Annapolis by IHG

5/5 Excellent

"Excellent from check in to check out, highly recommend!"

A verified traveller stayed at Crowne Plaza Annapolis by IHG

Posted 2 days ago

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

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

### Historic Inns of Annapolis

5/5 Excellent

"Love this inn for the location and ambience. The staff is always so friendly and accurate."

A verified traveller stayed at Historic Inns of Annapolis

Posted 3 days ago

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

![Fairfield Inn & Suites By Marriott Annapolis](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/ba30667e_y.jpg)

### Fairfield Inn & Suites By Marriott Annapolis

5/5 Excellent

"Rooms are clean, comfortable and give you a cool non-boxy vibe "

A verified traveller stayed at Fairfield Inn & Suites By Marriott Annapolis

Posted 4 days ago

[](https://expedia.ca/Annapolis-Hotels-Fairfield-Inn-Suites-By-Marriott-Annapolis.h100975886.Hotel-Information)

![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg)

### Hilton Garden Inn Annapolis Downtown

5/5 Excellent

"Excelente the staff and everything was very nice "

A verified traveller stayed at Hilton Garden Inn Annapolis Downtown

Posted 4 days ago

[](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information)

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

### Annapolis Waterfront Hotel, Autograph Collection

5/5 Excellent

"Great location, nice and clean "

A verified traveller stayed at Annapolis Waterfront Hotel, Autograph Collection

Posted 4 days ago

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

![Candlewood Suites Annapolis by IHG](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/f27fb62d_y.jpg)

### Candlewood Suites Annapolis by IHG

5/5 Excellent

"The room was very tidy. I love having a full size fridge as well as a microwave! These are great conveniences to have."

A verified traveller stayed at Candlewood Suites Annapolis by IHG

Posted 6 days ago

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

![Hilton Garden Inn Kent Island Marina](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/367a733a_y.jpg)

### Hilton Garden Inn Kent Island Marina

5/5 Excellent

"Spacious layout with lovely bay view. Quiet."

A verified traveller stayed at Hilton Garden Inn Kent Island Marina

Posted 6 days ago

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

## Frequently asked questions

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

> 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?

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

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

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- [Flights to Kent Island ](https://www.expedia.ca/Cheap-Flights-To-Kent-Island.d553248635077608788.Travel-Guide-Flights)
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- [Stevensville Vacation Rentals ](https://www.expedia.ca/Stevensville-Vacation-Rentals.d162393.Travel-Guide-VacationRentals)

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

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