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) ![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 # Find Hotels with a Pool in Chesapeake Beach, MD from CA $133 - ![](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 [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2025-11-20&endDate=2025-11-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2025-11-21&endDate=2025-11-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=88967&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=88967&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top 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) ![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) ![Interior](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4750fa1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rod 'N' Reel Resort Chesapeake Beach 8.4/10 Very good (1001) "Clean room, friendly & helpful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne CA $125 CA $167 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.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) ![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) ![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) ![Balcony view](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/1e3401a3.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 $154 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.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) ![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) ![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) ### Holiday Inn Express Prince Frederick by IHG Prince Frederick 8.8/10 Excellent (683) "Was clean and great area. Great breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darlene CA $144 CA $175 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Prince-Frederick-Hotels-Holiday-Inn-Express-Prince-Frederick.h281565.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661950/8dc6445a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661950/72d7a9c5.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) ### Springhill Suites by Marriott Prince Frederick Prince Frederick 8.6/10 Excellent (925) "This place is amazing, super clean and the staff is top notch " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $136 CA $151 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Prince-Frederick-Hotels-Springhill-Suites-By-Marriott-Prince-Frederick.h1661950.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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/08593556.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) ### 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 $145 CA $160 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.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) ![Waterfront Suite | Living area](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/0787536d.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 (88) "Very relaxing stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne CA $196 CA $277 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1650000/1644700/1644617/cfc0c560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Solomons Solomons 8.6/10 Excellent (637) "Was a great and pleasant experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARLON CA $150 CA $167 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Solomons-Hotels-Hilton-Garden-Inn-Solomons.h1644617.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/aabd7b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/a336c972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/488be20b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/10bef897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relaxing, peaceful house in Calvert County, Md close to beach towns and DC. Owings 10/10 Exceptional (48) "We love this place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joan K. CA $150 CA $349 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Close-To-North-Chesapeake-Beach.h71116837.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/e773fcbe.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) ![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) ### Sonesta ES Suites Annapolis Edgewater 8.8/10 Excellent (950) "Nice breakfast, clean room, great parking" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy CA $117 CA $133 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.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) ![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) ![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) ### Anchored Inn at Hidden Harbour Marina Deale 9.4/10 Exceptional (468) "Overnight stay - all went as expected" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $214 CA $244 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.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=2025-12-04&endDate=2025-12-05®ionId=88967&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chesapeake Beach Hotel Reviews ![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) ![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) ![Hilton Garden Inn Solomons](https://images.trvl-media.com/lodging/2000000/1650000/1644700/1644617/7fd50c6e_y.jpg) ### Hilton Garden Inn Solomons 10/10 Excellent "Everything you expect from a Hilton Garden Inn stay with no issues to report. " [](https://expedia.ca/Solomons-Hotels-Hilton-Garden-Inn-Solomons.h1644617.Hotel-Information) ![Holiday Inn Express Prince Frederick by IHG](https://images.trvl-media.com/lodging/1000000/290000/281600/281565/4e09e32f_y.jpg) ### Holiday Inn Express Prince Frederick by IHG 10/10 Excellent " Good" [](https://expedia.ca/Prince-Frederick-Hotels-Holiday-Inn-Express-Prince-Frederick.h281565.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 "Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay. " [](https://expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.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 clean hotel and convenient hotel location. Priced right, clise to d I wntown Annapolis and Town Center. Staff was superb " [](https://expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![Wingate by Wyndham Waldorf/Washington DC Area](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503681/599fcbb8_y.jpg) ### Wingate by Wyndham Waldorf/Washington DC Area 10/10 Excellent "The room was awesome " [](https://expedia.ca/Waldorf-Hotels-Baymont-By-Wyndham-Waldorf.h1503681.Hotel-Information) ![Quality Suites Waldorf](https://images.trvl-media.com/lodging/1000000/550000/543800/543785/407e0467_y.jpg) ### Quality Suites Waldorf 10/10 Excellent "The only thing was the room doesn’t have a curtain blocking the outside light." [](https://expedia.ca/Waldorf-Hotels-Comfort-Suites-Waldorf.h543785.Hotel-Information) ![Courtyard Marriott Waldorf](https://images.trvl-media.com/lodging/3000000/2310000/2301400/2301328/5e52a70b_y.jpg) ### Courtyard Marriott Waldorf 10/10 Excellent "Very clean " [](https://expedia.ca/Waldorf-Hotels-Courtyard-Marriott-Waldorf.h2301328.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. [Spark by Hilton Waldorf](https://www.expedia.ca/Waldorf-Hotels-Spark-By-Hilton-Waldorf.h26379.Hotel-Information): Features buffet, an indoor pool, and free self parking. [Holiday Inn Express Waldorf by IHG](https://www.expedia.ca/Waldorf-Hotels-Holiday-Inn-Express-Waldorf.h25493.Hotel-Information): Offers a snack bar/deli, a seasonal outdoor pool, and full. [Candlewood Suites Annapolis by IHG](https://www.expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information): Provides a snack bar/deli, an indoor pool, and daily. ### 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, Bruce Gabrielson's Surf Art Gallery and Museum, and Breezy Point Beach. 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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[Flights from Calvert County](https://www.expedia.ca/lp/flights/553248635083908238/flights-from-calvert-county) - [Chesapeake Beach Water Park](https://www.expedia.ca/Chesapeake-Beach-Water-Park-Chesapeake-Beach.d553248621532662257.Vacation-Attraction) - [Visit Churchton](https://www.expedia.ca/Churchton.dx6247936) - [Visit Dares Beach](https://www.expedia.ca/Dares-Beach.dx553248635975876513) - [Visit Deale](https://www.expedia.ca/Deale.dx55664) - [Car rental Deale](https://www.expedia.ca/Car-Rentals-In-Deale.d55664.Car-Rental-Guide) - [Car rental North Beach](https://www.expedia.ca/Car-Rentals-In-North-Beach.d138967.Car-Rental-Guide) - [Record Rent A Car Rental Cars in Sunderland](https://www.expedia.ca/Record-Rent-A-Car-Car-Rentals-In-Sunderland.d3000440915-c30.Car-Rental-Guide-Suppliers) - [Things to do in Calvert County](https://www.expedia.ca/Things-To-Do-In-Calvert-County.d553248635083908238.Travel-Guide-Activities) - [Book Hotels with a Pool in Chesapeake Beach on Expedia.com](https://www.expedia.com/Chesapeake-Beach-Hotels-Hotel-With-Pool.0-0-d88967-tHotelwithPool.Travel-Guide-Filter-Hotels)