Title: Book the Best Hotels with POOL in Chester in 2025 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d3000440455.Travel-Guide-Hotels)[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 with a Pool in Chester, MD from CA $125 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chester Hotels with a Pool Tonight [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-11-21&endDate=2025-11-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 22 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-11-22&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Hotels with a Pool ![Indoor pool, open 5 AM to 11 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/b307a535.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/6468097d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Kent Island Marina Grasonville 9.0/10 Wonderful (1001) "Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberta CA $143 CA $159 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/cd0addda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/16010c68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/4e51f020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/fbc96e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Easton 7.6/10 Good (816) "Everything was clean; staff friendly; breakfast great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $114 CA $125 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Easton-Hotels-Quality-Inn.h11364.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/67743db3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/1e3401a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/25d29217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Second Floor Bay View Double Room with Balcony ](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/4f8f8af7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Knapps Narrows Marina & Inn Tilghman 9.4/10 Exceptional (355) "Yes. room was spotless and staff was awesome!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank CA $140 CA $155 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/26f606ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/76eda657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/ac21726a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/5f0e7ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### St Michaels Inn St. Michaels 8.2/10 Very good (1000) "clean and comfy, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tamara CA $147 CA $162 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/068178f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3968d160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/160d338a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/c77ff2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Kent Narrows Inn Grasonville 8.0/10 Very good (1001) "Our room was clean, smelled great, and the breakfast was good with many options." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $129 CA $143 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/b2a10ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/028c45ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/ead5e21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/76d50f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Grasonville 7.8/10 Good (852) "room was nice breakfast was good and the staff was very friendly and helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Esai CA $130 CA $145 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.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) ![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) ![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 (125) "The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $176 CA $245 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![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) ![1 bedroom, hypo-allergenic bedding, desk, blackout drapes](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) ### Country Inn & Suites by Radisson, Annapolis, MD Annapolis 9.0/10 Wonderful (1001) "Wonderful country inn!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $125 CA $142 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/97d2d16a.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.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 (924) "nice, clean, up to date, budget friendly hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) mike CA $134 CA $149 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/97742239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/w1504h992x0y8-f18eeee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/e5b90fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/baedfd04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Easton Easton 9.0/10 Wonderful (547) "Super pet friendly, fresh cookies, and very clean rooms. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan CA $180 CA $198 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Easton-Hotels-Hampton-Inn-Easton.h1432437.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=2025-12-05&endDate=2025-12-06®ionId=3000440455&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_3000440455) ## Top Chester Hotel Reviews ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Everything was great" [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Hampton Inn & Suites Annapolis](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/23865424_y.jpg) ### Hampton Inn & Suites Annapolis 10/10 Excellent "The courtesy of the staff. " [](https://expedia.ca/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) ![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg) ### St Michaels Inn 10/10 Excellent "This is a charming little inn conveniently located right in St Michaels. The staff was great, the rooms clean, and plenty of parking. In the warmer months you can enjoy the pool and roomy outdoor seating areas." [](https://expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.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 10/10 Excellent "Very good clean rooms location and comfortable " [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.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 10/10 Excellent "Friendly staff. Enjoyed the room. " [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "Our room had a large bed along with a pull out sofa. I didn’t realize we would have a kitchen with stove, fridge, plates, and cookware. The room was spacious, the pool was fun to hang out. " [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![SpringHill Suites by Marriott Annapolis](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg) ### SpringHill Suites by Marriott Annapolis 10/10 Excellent "very friendly staff" [](https://expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg) ### The Westin Annapolis 10/10 Excellent "Amazing " [](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Courtyard by Marriott Annapolis](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/122348e3_y.jpg) ### Courtyard by Marriott Annapolis 10/10 Excellent "The staff was extremely courteous! Most especially, Teresa DuBose, the Operational Manager, that went out of her way to make our stay fantastic! " [](https://expedia.ca/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Chester? > [Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!](https://www.expedia.ca/Chester-Hotels-Waterfront-Home-On-3-Acres-Fish.h33554342.Hotel-Information): Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. [Historic Inns of Annapolis](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information): Offers buffet, an indoor pool, and free self parking. [DoubleTree by Hilton Hotel Annapolis](https://www.expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information): Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. [Graduate by Hilton Annapolis](https://www.expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information): Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool, and a snack bar/deli. [Sonesta ES Suites Annapolis](https://www.expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information): Features buffet, a seasonal outdoor pool, and complimentary wired internet access. ### What is there to see and do in Chester? > Enjoy a stroll along the shore at Sandy Point Beach and Bay Ridge Beach. Discover sights such as Northern Chesapeake Bay, Matapeake State Park, and Eastern Neck National Wildlife Refuge during your stay. ### When is the best time to book a hotel with a pool in Chester? > You may want to think about a place to stay with an outdoor swimming pool if you plan to visit Chester in the warmest months of July, August, or June when the average temperature is 74°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temp is 39°F. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [5 Star Hotels in Kent Island](https://www.expedia.ca/5Star-Kent-Island-Hotels.s50-0-d553248635077608788.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Stevensville](https://www.expedia.ca/5Star-Stevensville-Hotels.s50-0-d162393.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Boutique-Hotel.0-n553248635976473602-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Hotels-With-Hot-Tubs.0-n553248635976473602-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Lake Hotels in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Lake-Hotels.0-n553248635976473602-0-tLakeHotels.Travel-Guide-Filter-Hotels) - 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