Title: Book the Best Hotels with POOL in Chesapeake Beach in 2026 | Expedia.ca [Chesapeake Beach Travel Guide](https://expedia.ca/Chesapeake-Beach.dx88967)[Hotels in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Hotels.d88967.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Vacation-Rentals.d88967.Travel-Guide-VacationRentals)[Chesapeake Beach Car Rentals](https://expedia.ca/Car-Rentals-In-Chesapeake-Beach.d88967.Car-Rental-Guide)[Chesapeake Beach Vacation Packages](https://expedia.ca/Chesapeake-Beach.d88967.Destination-Travel-Guides) ![Boardwalk along the Chesapeake Bay.](https://images.trvl-media.com/place/88967/e2079c3a-0245-4a90-abab-4255f259a6e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ronanne Vinson ![](https://images.trvl-media.com/place/88967/e2079c3a-0245-4a90-abab-4255f259a6e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Chesapeake Beach Hotels with a Pool Tonight [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2026-01-14&endDate=2026-01-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 15 - Jan 16](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2026-01-15&endDate=2026-01-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesapeake Beach hotels with a pool ![Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/9f6ae80a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4750fa1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/43373394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/d3121313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rod 'N' Reel Resort [](https://www.expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) Chesapeake Beach 8.4/10 Very good (1,000 reviews) "Really liked the new Rod n Reel. Everything checked out. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pablo CA $105 CA $144 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.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/bc6750c1.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) ![Dining](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/e9e3336f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/5eb26742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### St Michaels Inn [](https://www.expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) St. Michaels 8.2/10 Very good (1,000 reviews) "Good value and close to downtown." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $135 CA $149 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.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) ![View from property](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/e01c273a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/d898936b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/86e1ff48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Knapps Narrows Marina & Inn [](https://www.expedia.ca/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.Hotel-Information) Tilghman 9.4/10 Exceptional (365 reviews) "nice clean room staff very nice would stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) mario CA $139 CA $153 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/6e7f4df6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/0efeb5e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/c982427d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/8af764c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wylder Tilghman Island [](https://www.expedia.ca/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information) Tilghman 8.8/10 Excellent (91 reviews) "Very relaxing stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne CA $161 CA $238 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information) ![Indoor pool, free cabanas](https://images.trvl-media.com/lodging/1000000/30000/25500/25493/d6e164ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/1000000/30000/25500/25493/bf8dbd62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/30000/25500/25493/9a1d7d08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25500/25493/cb263920.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Waldorf by IHG [](https://www.expedia.ca/Waldorf-Hotels-Holiday-Inn-Express-Waldorf.h25493.Hotel-Information) Waldorf 8.2/10 Very good (1,001 reviews) "The breakfast was very good. Rooms were very clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra CA $136 CA $151 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Waldorf-Hotels-Holiday-Inn-Express-Waldorf.h25493.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/06cdc3cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/814e7667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/da259258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/8dfe0c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anchored Inn at Hidden Harbour Marina [](https://www.expedia.ca/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information) Deale 9.4/10 Exceptional (473 reviews) "Beautiful place to stay, we stay their one to two times a year." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marjorie CA $186 CA $212 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661950/a89ed648.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661950/caa02936.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661950/744584e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661950/f2d60961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Springhill Suites by Marriott Prince Frederick [](https://www.expedia.ca/Prince-Frederick-Hotels-Springhill-Suites-By-Marriott-Prince-Frederick.h1661950.Hotel-Information) Prince Frederick 8.6/10 Excellent (945 reviews) "The room was clean & very comfortable. Check-in was easy & the desk clerk was very helpful. The breakfast buffet was great with a lot of very good options. Have stayed here several times and have never been disappointed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judith CA $158 CA $176 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Prince-Frederick-Hotels-Springhill-Suites-By-Marriott-Prince-Frederick.h1661950.Hotel-Information) ![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) ![Egyptian cotton sheets, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/c12dde92.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) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/a8e6d435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta ES Suites Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) Edgewater 8.8/10 Excellent (976 reviews) "Plenty of space for our group - nice layout! Nice showers & very clean! Breakfast was exceptional! Very pleased with the stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammy CA $126 CA $144 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1650000/1644700/1644617/148fc459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1650000/1644700/1644617/b6e72f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/2000000/1650000/1644700/1644617/664d45fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1650000/1644700/1644617/0b056987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Solomons [](https://www.expedia.ca/Solomons-Hotels-Hilton-Garden-Inn-Solomons.h1644617.Hotel-Information) Solomons 8.6/10 Excellent (642 reviews) "Was a great and pleasant experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARLON CA $159 CA $177 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Solomons-Hotels-Hilton-Garden-Inn-Solomons.h1644617.Hotel-Information) ![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) ![Boating](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/b187b396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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 [](https://www.expedia.ca/Tilghman-Hotels-The-Tilghman-Island-Inn.h59854328.Hotel-Information) Tilghman 9.6/10 Exceptional (121 reviews) "Great room and water view! Staff is very friendly and welcoming. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole CA $278 CA $305 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29®ionId=88967&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chesapeake Beach Hotel Reviews ![Rod 'N' Reel Resort](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5_y.jpg) ### Rod 'N' Reel Resort 10/10 Excellent "perfect bed, perfect shower, yummy coffee. even encountered a Great blue heron. thank you so much, Ron 'N' Reel!" [](https://expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.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 "Great " [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Residence Inn by Marriott Waldorf](https://images.trvl-media.com/lodging/3000000/2680000/2675800/2675705/7669562a_y.jpg) ### Residence Inn by Marriott Waldorf 10/10 Excellent "Yea it was good and nice " [](https://expedia.ca/Waldorf-Hotels-Residence-Inn-By-Marriott-Waldorf.h2675705.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 "We use this property for business travel .Good clean property, nice location. Good breakfast and coffee. Reasonably priced (except parking fee)" [](https://expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![Springhill Suites by Marriott Prince Frederick](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661950/39882431_y.jpg) ### Springhill Suites by Marriott Prince Frederick 10/10 Excellent "The room was clean & very comfortable. Check-in was easy & the desk clerk was very helpful. The breakfast buffet was great with a lot of very good options. Have stayed here several times and have never been disappointed." [](https://expedia.ca/Prince-Frederick-Hotels-Springhill-Suites-By-Marriott-Prince-Frederick.h1661950.Hotel-Information) ![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg) ### Inn at Perry Cabin 10/10 Excellent "We had a great stay, hotel was very clean and food was great" [](https://expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![Hilton Garden Inn Solomons](https://images.trvl-media.com/lodging/2000000/1650000/1644700/1644617/7fd50c6e_y.jpg) ### Hilton Garden Inn Solomons 10/10 Excellent "Arrived early , still able to get checked in. Minor problem with electronic door locks , but handled prompley." [](https://expedia.ca/Solomons-Hotels-Hilton-Garden-Inn-Solomons.h1644617.Hotel-Information) ![Towneplace Suites by Marriott Clinton at Joint Base Andrews](https://images.trvl-media.com/lodging/3000000/2310000/2308600/2308579/eb7a3f7b_y.jpg) ### Towneplace Suites by Marriott Clinton at Joint Base Andrews 10/10 Excellent "I grabbed a yogurt and didi not have time to enjoy a full breakfast. " [](https://expedia.ca/Waldorf-Hotels-Towneplace-Suites-By-Marriott-Clinton-At-Joint-Base-Andrews.h2308579.Hotel-Information) ![Holiday Inn Express Waldorf by IHG](https://images.trvl-media.com/lodging/1000000/30000/25500/25493/9a1d7d08_y.jpg) ### Holiday Inn Express Waldorf by IHG 10/10 Excellent "My room was clean and well kept. The staff was very friendly and helpful. I was glad to see a turkey bacon option at breakfast. The breakfast buffet was nice. " [](https://expedia.ca/Waldorf-Hotels-Holiday-Inn-Express-Waldorf.h25493.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Chesapeake Beach? ### What is there to see and do in Chesapeake Beach? ### When is the best time to book a hotel with a pool in Chesapeake Beach? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [5 Star Hotels in Rose Haven ](https://www.expedia.ca/5Star-Rose-Haven-Hotels.s50-0-d153066.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Hotels-With-A-Lazy-River.0-0-d178235-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Benedict ](https://www.expedia.ca/Benedict-Hotels-Cheap-Hotels.0-0-d3000347809-tCheapHotels.Travel-Guide-Filter-Hotels) - 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