Title: Book the Best Hotels with POOL in Massey in 2025 | Expedia.ca [Hotels in Massey](https://expedia.ca/Massey-Hotels.d3000440702.Travel-Guide-Hotels)[Vacation Rentals in Massey](https://expedia.ca/Massey-Vacation-Rentals.d3000440702.Travel-Guide-VacationRentals)[Massey Car Rentals](https://expedia.ca/Car-Rentals-In-Massey.d3000440702.Car-Rental-Guide)[Massey Vacation Packages](https://expedia.ca/Massey.d3000440702.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Massey, MD ![](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 Massey Hotels with a Pool Tonight [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=3000440702&startDate=2025-10-19&endDate=2025-10-20&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=3000440702&startDate=2025-10-20&endDate=2025-10-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=3000440702&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=3000440702&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Massey Hotels with a Pool ![Lobby](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/b37bb6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 restaurants, breakfast, dinner, brunch served; Italian cuisine](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/627f8961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Treatment room](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/df9b48b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 restaurants, breakfast, dinner, brunch served; Italian cuisine](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/6194bcdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bally's Dover Casino Resort Dover 8.8/10 Excellent (3208) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $100 CA $137 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/600000/597800/597727/197f84f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/600000/597800/597727/eb92d4c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/600000/597800/597727/2f695952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/600000/597800/597727/286149bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Dover by IHG Dover 8.8/10 Excellent (1004) "We stay here every year and love it. Rooms are really spacious and clean. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Hoang Tram CA $157 CA $174 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Dover-Hotels-Holiday-Inn-Express-Hotel-Suites-Dover.h597727.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1840000/1831100/1831095/5ce1d09b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1840000/1831100/1831095/c1d84f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1840000/1831100/1831095/a7d5fb8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1840000/1831100/1831095/d6298f2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Dover 8.8/10 Excellent (1007) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) james CA $116 CA $129 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Dover-Hotels-Comfort-Inn-Suites.h1831095.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2240000/2232400/2232384/73c245f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2240000/2232400/2232384/w3837h2557x3y3-582029e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2240000/2232400/2232384/e0530621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 16.00 per person)](https://images.trvl-media.com/lodging/3000000/2240000/2232400/2232384/eab21539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Dover Dover 8.8/10 Excellent (1007) "Great staff n facility " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Annette CA $148 CA $165 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Dover-Hotels-Hilton-Garden-Inn-Dover.h2232384.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/4dc8f4ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/959c2292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/da06d995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown Chestertown 8.6/10 Excellent (831) "The thermostat controls were easy to adjust. Night desk lady was friendly and pleasant. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charlie CA $143 CA $159 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/791afcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/a0c80d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/53ee3fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Middletown Middletown 9.2/10 Wonderful (295) "One of the best hotels I have ever stayed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jean CA $151 CA $168 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/726148e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6cc4a825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/50463ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/c38ba9d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Middletown Middletown 8.8/10 Excellent (843) "Enjoyed the amenities and great location for shops nearby " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $140 CA $156 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/42300/42248/1185bc50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/42300/42248/2a23e7f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/1000000/50000/42300/42248/7377e77e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/42300/42248/41c3a52c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Dover Dover 7.2/10 Good (1006) " Clean and comfortable and walking distance for food options " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom CA $119 CA $133 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Dover-Hotels-Comfort-Suites-Dover.h42248.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2120000/2115100/2115064/d83a3b46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2120000/2115100/2115064/558d764a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2120000/2115100/2115064/e37ca31f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2120000/2115100/2115064/06272618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn And Suites Dover 8.4/10 Very good (1006) "Nathan or Nate was professional, efficient and polite at the front desk." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rickie CA $132 CA $146 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Dover-Hotels-Sleep-Inn-And-Suites.h2115064.Hotel-Information) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/817be2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/e1ce6cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/b90292fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/8628f41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Smyrna 7.6/10 Good (1008) "Wonerful place, all good..Hotel,area, staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $124 CA $138 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Dover-Hotels-Quality-Inn.h1781239.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=2025-11-02&endDate=2025-11-03®ionId=3000440702&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Massey Hotel Reviews ## Frequently asked questions ### What are some hotels with pools in Massey? > [Bally's Dover Casino Resort](https://www.expedia.ca/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.Hotel-Information): Hotel steps from Dover Downs Casino. Features 5 restaurants, an indoor pool, and 5 bars. [Comfort Inn & Suites](https://www.expedia.ca/Dover-Hotels-Comfort-Inn-Suites.h1831095.Hotel-Information): Hotel located near Dover Downs Casino. Offers buffet, an indoor pool, and complimentary wired internet access. [Red Roof Inn & Suites Dover Downtown](https://www.expedia.ca/Dover-Hotels-Red-Roof-Inn-Suites-Dover-Downtown.h887960.Hotel-Information): Features buffet, an indoor pool, and complimentary wired internet access. [Holiday Inn Express & Suites Middletown by IHG](https://www.expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information): Hotel located near Dover Downs Casino. Offers daily, a seasonal outdoor pool, and free self parking. [Comfort Suites Dover](https://www.expedia.ca/Dover-Hotels-Comfort-Suites-Dover.h42248.Hotel-Information): Features 20 restaurants, an indoor pool, and buffet. ### What is there to see and do in Massey? > The picturesque setting of Betterton Beach and Chestertown Dog Park showcase the area's natural beauty. Discover sights such as Tilmon's Island Winery, Hack's Point Marina, and Middletown Town Hall during your stay. ### When is the best time to book a hotel with a pool in Massey? > You may want to think about a place to stay that has an outdoor pool if you plan to visit Massey in the warmest months of July, August, or June when the average temp is 73°F. Lodging offering an indoor pool may be the way to go if you come to town 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 - More ways to book - [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) - [Apartments in Betterton](https://www.expedia.ca/Betterton-Apartments.d3000440429-aaApartments.Travel-Guide-Accommodation) - [Hotels near Betterton Beach](https://www.expedia.ca/Betterton-Beach-Hotels.0-l553248635983992889-0.Travel-Guide-Filter-Hotels) - [Cottages in Betterton](https://www.expedia.ca/Betterton-Cottages.d3000440429-aaCottages.Travel-Guide-Accommodation) - [Betterton Hotels](https://www.expedia.ca/Betterton-Hotels.d3000440429.Travel-Guide-Hotels) - 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