Title: Book the Best Hotels with POOL in Chesapeake Beach in 2025 | 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)[Things to do in Chesapeake Beach](https://expedia.ca/Things-To-Do-In-Chesapeake-Beach.d88967.Travel-Guide-Activities)[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) ![](https://mediaim.expedia.com/destination/2/a9547e3e3a06984ae8df1712c3d277fb.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ronanne Vinson # Find Hotels with a Pool in Chesapeake Beach, MD from CA $141 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2025-10-05&endDate=2025-10-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2025-10-06&endDate=2025-10-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chesapeake Beach Hotels with a Pool ![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) ![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) ![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) ### Knapps Narrows Marina & Inn Tilghman 9.4/10 Exceptional (342) "Beautiful view!" CA $140 CA $153 total includes taxes & fees Oct 7 - Oct 8 [](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) ![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) ![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) ![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 (1002) "Great location, free parking, free breakfast excellent staff." CA $128 CA $141 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/90332b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/48995b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, Garden View | Private kitchen](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/c6a32c3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House | In-room dining](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/49f997cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Legacy Villa Upper Marlboro CA $235 CA $265 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Upper-Marlboro-Hotels-Legacy-Villa.h114870697.Hotel-Information) ![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) ![Marina](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/27bb8cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Studio Suite | Balcony](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5.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 Chesapeake Beach 8.4/10 Very good (1001) "Great place to stay." CA $187 CA $236 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/290000/281600/281565/d4acde56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/290000/281600/281565/56ebe044.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/281600/281565/fc7bcc94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/290000/281600/281565/6371b691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Prince Frederick by IHG Prince Frederick 8.8/10 Excellent (671) "Will be stay again soon " CA $144 CA $175 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Prince-Frederick-Hotels-Holiday-Inn-Express-Prince-Frederick.h281565.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/937d59ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/72a927ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Widows Walk Suite | Terrace/patio](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/ba45b764.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) ### Wylder Tilghman Island Tilghman 8.8/10 Excellent (82) "Very relaxing stay." CA $236 CA $321 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661950/0adf657e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661950/39882431.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661950/8dc6445a.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 Prince Frederick 8.6/10 Excellent (917) "clean, quiet and helpful staff." CA $148 CA $164 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Prince-Frederick-Hotels-Springhill-Suites-By-Marriott-Prince-Frederick.h1661950.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1650000/1644700/1644617/7fd50c6e.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) ![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 Solomons 8.6/10 Excellent (627) "Nice Stay" CA $177 CA $197 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Solomons-Hotels-Hilton-Garden-Inn-Solomons.h1644617.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/662e8b88.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) ![Marina](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/f924cfad.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 Deale 9.4/10 Exceptional (456) "The view from the balcony is the best, whether at night or the day time. The outside bar everyone is so friendly. I have stayed here a few times and every time I come to the area, I will only stay here. I highly recommend it !" CA $250 CA $285 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/65faa113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free breakfast](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/81d032fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 Deluxe Double, queen fire place](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/6d7108e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/6594eb94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### George Brooks House B&B St. Michaels 8.6/10 Excellent (64) "Gorgeous quaint historic house. Friendly owner, close to town " CA $276 CA $304 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.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=2025-10-20&endDate=2025-10-21®ionId=88967&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chesapeake Beach Hotel Reviews ![Holiday Inn Express Waldorf by IHG](//images.trvl-media.com/lodging/1000000/30000/25500/25493/9a1d7d08_y.jpg) ### Holiday Inn Express Waldorf by IHG 10/10 Excellent "Clean and the food is good. " [](https://expedia.ca/Waldorf-Hotels-Holiday-Inn-Express-Waldorf.h25493.Hotel-Information) ![Rod 'N' Reel Resort](//images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5_y.jpg) ### Rod 'N' Reel Resort 10/10 Excellent "Everything was so nice " [](https://expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Sonesta ES Suites Annapolis](//images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "The hotel was nice. The first room I got was still a mess because housekeeping didn’t clean that room. So I was given another room, which was clean as a whistle. Very good stay. I would definitely go back. Service was top tier." [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Anchored Inn at Hidden Harbour Marina](//images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/1068537c_y.jpg) ### Anchored Inn at Hidden Harbour Marina 10/10 Excellent "The view from the balcony is the best, whether at night or the day time. The outside bar everyone is so friendly. I have stayed here a few times and every time I come to the area, I will only stay here. I highly recommend it !" [](https://expedia.ca/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information) ![Residence Inn by Marriott Waldorf](//images.trvl-media.com/lodging/3000000/2680000/2675800/2675705/7669562a_y.jpg) ### Residence Inn by Marriott Waldorf 10/10 Excellent "Nice suite. Terribly noisy. It’s 2:21 am and doors are shutting loudly. It’s a nice room, but not much sleep. " [](https://expedia.ca/Waldorf-Hotels-Residence-Inn-By-Marriott-Waldorf.h2675705.Hotel-Information) ![Courtyard Marriott Waldorf](//images.trvl-media.com/lodging/3000000/2310000/2301400/2301328/5e52a70b_y.jpg) ### Courtyard Marriott Waldorf 10/10 Excellent "Nice stay." [](https://expedia.ca/Waldorf-Hotels-Courtyard-Marriott-Waldorf.h2301328.Hotel-Information) ![Hilton Garden Inn Solomons](//images.trvl-media.com/lodging/2000000/1650000/1644700/1644617/7fd50c6e_y.jpg) ### Hilton Garden Inn Solomons 10/10 Excellent "Nice Stay" [](https://expedia.ca/Solomons-Hotels-Hilton-Garden-Inn-Solomons.h1644617.Hotel-Information) ![Wingate by Wyndham Waldorf/Washington DC Area](//images.trvl-media.com/lodging/2000000/1510000/1503700/1503681/599fcbb8_y.jpg) ### Wingate by Wyndham Waldorf/Washington DC Area 10/10 Excellent "For what we paid, it was a great hotel. It was clean and quiet. There was ample parking and the front desk was professional. Its not luxury but I didnt pay for luxury. Felt it was worth it and its near alot of things. Not walkable, but its drivable. Near other hotels. " [](https://expedia.ca/Waldorf-Hotels-Baymont-By-Wyndham-Waldorf.h1503681.Hotel-Information) ![St Michaels Inn](//images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg) ### St Michaels Inn 10/10 Excellent "Easy Check In & quite area" [](https://expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Chesapeake Beach? > [Rod 'N' Reel Resort](https://www.expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information): Features a seasonal outdoor pool, an indoor pool, and 2 restaurants. [Sonesta ES Suites Annapolis](https://www.expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information): Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. [SpringHill Suites by Marriott Annapolis](https://www.expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information): Provides a snack bar/deli, an indoor pool, and daily. [St Michaels Inn](https://www.expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information): Features daily, a seasonal outdoor pool, and free self parking. [The Wildset](https://www.expedia.ca/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information): Offers a full-service spa, an outdoor pool, and 2 bars. ### What is there to see and do in Chesapeake Beach? > Make a point to visit attractions like Chesapeake Beach Water Park and Chesapeake Beach Railway Museum. During your stay, check out sights such as Rod n Reel Charter Fishing, Breezy Point Beach, and Bruce Gabrielson's Surf Art Gallery and Museum. The beaches and restaurants are just some of the things to enjoy while you're in the area. ### When is the best time to book a hotel with a pool in Chesapeake Beach? > You may want to consider an accommodation with an outdoor swimming pool if you plan to visit Chesapeake Beach in the hottest months of July, August, or June when the average temperature is 75°F. 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