Title: Book the Best Hotels with POOL in Montego Bay in 2026 | Expedia.ca [Vacation Rentals in Ocean City](https://expedia.ca/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals)[Flights to Ocean City](https://expedia.ca/Cheap-Flights-To-Ocean-City.d9151.Travel-Guide-Flights)[Things to do in Ocean City](https://expedia.ca/Things-To-Do-In-Ocean-City.d9151.Travel-Guide-Activities)[Montego Bay Car Rentals](https://expedia.ca/Car-Rentals-In-Montego-Bay.d553248635976479127.Car-Rental-Guide)[Montego Bay Vacations](https://expedia.ca/Montego-Bay.d553248635976479127.Destination-Travel-Guides) ![Assateague Island Wild Ponies on the Beach](https://images.trvl-media.com/place/553248635976479127/e0dbbd5e-3261-4bdf-8ca4-d3650dac5032.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Montego Bay, MD from CA $91 - ![](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 Montego Bay Hotels with a Pool Tonight [Dec 20 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976479127&startDate=2025-12-20&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976479127&startDate=2025-12-21&endDate=2025-12-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976479127&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976479127&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Montego Bay hotels with a pool ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/df24e03e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/ad9cdd0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/8ccc8362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/7811430e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Hotel Ocean City Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-Grand-Hotel-Ocean-City-Oceanfront.h800771.Hotel-Information) Downtown Ocean City 9.0/10 Wonderful (3358) "Yes, I great place y to o stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $66 CA $94 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Ocean-City-Hotels-Grand-Hotel-Ocean-City-Oceanfront.h800771.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/9000000/8310000/8308900/8308889/82eaf0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/9000000/8310000/8308900/8308889/8c7cbe42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/9000000/8310000/8308900/8308889/7a6e2611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/9000000/8310000/8308900/8308889/7773575b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fenwick Shores, Tapestry Collection by Hilton [](https://www.expedia.ca/Rehoboth-Beach-Hotels-Fenwick-Shores.h8308889.Hotel-Information) Fenwick Island 9.4/10 Exceptional (697) "Another great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $112 CA $125 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Rehoboth-Beach-Hotels-Fenwick-Shores.h8308889.Hotel-Information) ![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/9050a3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/e607fa92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/41a02ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/54e2685b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Place Hotel [](https://www.expedia.ca/Ocean-City-Hotels-Park-Place-Hotel.h13279522.Hotel-Information) Downtown Ocean City 9.2/10 Wonderful (1058) "Great location, friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yun-Ping [](https://www.expedia.ca/Ocean-City-Hotels-Park-Place-Hotel.h13279522.Hotel-Information) ![Indoor pool, open 6:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/2ddc1565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; beach views](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/406f4e95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/5bca3c15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee shop](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/b7952863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Ocean City Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-Dunes-Manor-Hotel-And-Dunes-Suites.h7731419.Hotel-Information) Midtown Ocean City 9.0/10 Wonderful (1103) "Love the fact that the hotel is footsteps away from the beach and the view is amazing!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elliott CA $101 CA $113 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Ocean-City-Hotels-Dunes-Manor-Hotel-And-Dunes-Suites.h7731419.Hotel-Information) ![Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/2b54bb5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed, Balcony, Partial Ocean View | View from room](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/9ca3b695.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/a68045c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/49cf595a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Ocean City Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-DoubleTree-By-Hilton-Ocean-City-Oceanfront.h15096.Hotel-Information) Midtown Ocean City 9.0/10 Wonderful (1000) "Beautiful and spotless room. The oceanfront view was so nice to wake up to in the morning. The staff were all very friendly. The restaurant on site Marlin Moon was outstanding. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin CA $115 CA $129 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Ocean-City-Hotels-DoubleTree-By-Hilton-Ocean-City-Oceanfront.h15096.Hotel-Information) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/6000000/5130000/5121500/5121459/1116dd7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5130000/5121500/5121459/w5760h3835x0y5-8a7d75bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5130000/5121500/5121459/w5760h3835x0y5-52ff0f65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/6000000/5130000/5121500/5121459/w5760h3837x0y0-4aa509f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Ocean City/Bayfront-Convention Center [](https://www.expedia.ca/Ocean-City-Hotels-Hampton-Inn-Suites-Ocean-City.h5121459.Hotel-Information) Midtown Ocean City 8.8/10 Excellent (1000) "Very clean comfortable stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keiyanna CA $81 CA $91 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Ocean-City-Hotels-Hampton-Inn-Suites-Ocean-City.h5121459.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/70000/63000/62960/c71224e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/70000/63000/62960/97e80f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/70000/63000/62960/2fcfbe0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds (No Pets Allowed)](https://images.trvl-media.com/lodging/1000000/70000/63000/62960/w1199h797x1y1-f09ca5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fenwick Inn [](https://www.expedia.ca/Ocean-City-Hotels-Fenwick-Inn.h62960.Hotel-Information) North Ocean City 8.8/10 Excellent (2000) "Clean room, friendly staff. Great roof top bar/restaurant." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jane [](https://www.expedia.ca/Ocean-City-Hotels-Fenwick-Inn.h62960.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/83b7c1f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/793897ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/a9dfd72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/w3837h2556x3y3-8b958879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Ocean City / Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-Hyatt-Place-Ocean-City-Oceanfront.h23511859.Hotel-Information) Downtown Ocean City 9.0/10 Wonderful (1590) "Room was excellent, very clean, not dated at all, location oceanfront was great - fantastic view of the sunrise. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $109 CA $123 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Ocean-City-Hotels-Hyatt-Place-Ocean-City-Oceanfront.h23511859.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879813/895b5f01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879813/435b930e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879813/w4500h2777x0y0-067da199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879813/2f5a06d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru by Hilton Ocean City Bayside [](https://www.expedia.ca/Ocean-City-Hotels-Tru-By-Hilton-Ocean-City-Bayside.h48879813.Hotel-Information) Midtown Ocean City 9.0/10 Wonderful (1004) "Clean rooms, safe parking and very friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Criss CA $95 CA $106 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Ocean-City-Hotels-Tru-By-Hilton-Ocean-City-Bayside.h48879813.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1990000/1981500/1981450/065faa68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1990000/1981500/1981450/b01386b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![NEW Building - Standard Room, 2 Double Beds, City View | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1990000/1981500/1981450/342df8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![NEW Building - Deluxe Room, 2 Double Beds, Bay View](https://images.trvl-media.com/lodging/2000000/1990000/1981500/1981450/3fa4f773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Bum Inn [](https://www.expedia.ca/Ocean-City-Hotels-Beach-Bum-Inn.h1981450.Hotel-Information) Downtown Ocean City 8.2/10 Very good (235) "Room was clean and just gave off that Beach Vibe. The staff was very friendly. OCMD best kept secret. We will be back! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James [](https://www.expedia.ca/Ocean-City-Hotels-Beach-Bum-Inn.h1981450.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=2026-01-03&endDate=2026-01-04®ionId=553248635976479127&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Montego Bay Hotel Reviews ![Grand Hotel Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/35e46ff3_y.jpg) ### Grand Hotel Ocean City Oceanfront 10/10 Excellent "Courteous staff, nice clean room with ocean view " [](https://expedia.ca/Ocean-City-Hotels-Grand-Hotel-Ocean-City-Oceanfront.h800771.Hotel-Information) ![Hilton Ocean City Oceanfront Suites](https://images.trvl-media.com/lodging/1000000/30000/27700/27630/502613d6_y.jpg) ### Hilton Ocean City Oceanfront Suites 10/10 Excellent "the room was spotless-and I am picky! The staff was friendly and helpful." [](https://expedia.ca/Ocean-City-Hotels-Hilton-Ocean-City-Oceanfront-Suites.h27630.Hotel-Information) ![Hilton Garden Inn Ocean City Oceanfront](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/10d78993_y.jpg) ### Hilton Garden Inn Ocean City Oceanfront 10/10 Excellent "Friendly staff, clean hotel, great food and service at Solstice as well! Late check out was a bonus too! Thank you for your Hospitality " [](https://expedia.ca/Ocean-City-Hotels-Dunes-Manor-Hotel-And-Dunes-Suites.h7731419.Hotel-Information) ![Fenwick Inn](https://images.trvl-media.com/lodging/1000000/70000/63000/62960/971dc050_y.jpg) ### Fenwick Inn 10/10 Excellent "Yes " [](https://expedia.ca/Ocean-City-Hotels-Fenwick-Inn.h62960.Hotel-Information) ![Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/10000/2300/2292/e439a1ab_y.jpg) ### Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront 10/10 Excellent "The hotel is older, but the rooms are updated. We’ve stayed here many times. They’re pet friendly, which is a big plus. " [](https://expedia.ca/Ocean-City-Hotels-Howard-Johnson-Plaza-Hotel-By-Wyndham-Ocean-City-Oceanfront.h2292.Hotel-Information) ![Gold Leaf Hotel of Dewey - Rehoboth Beach](https://images.trvl-media.com/lodging/18000000/17450000/17444200/17444119/1e642696_y.jpg) ### Gold Leaf Hotel of Dewey - Rehoboth Beach 10/10 Excellent "Clean room" [](https://expedia.ca/Rehoboth-Beach-Hotels-Gold-Leaf-Hotel-Of-Dewey-Rehoboth-Beach.h17444119.Hotel-Information) ![Hyatt Place Dewey Beach](https://images.trvl-media.com/lodging/7000000/6100000/6099400/6099301/8944382c_y.jpg) ### Hyatt Place Dewey Beach 10/10 Excellent "Awesome " [](https://expedia.ca/Rehoboth-Beach-Hotels-Hyatt-Place-Dewey-Beach.h6099301.Hotel-Information) ![Carousel Resort Hotel & Condominiums](https://images.trvl-media.com/lodging/1000000/20000/16200/16138/72fa8dcb_y.jpg) ### Carousel Resort Hotel & Condominiums 10/10 Excellent "Yes, everything was great, i love this hotel" [](https://expedia.ca/Ocean-City-Hotels-Carousel-Resort-Hotel-Condominiums.h16138.Hotel-Information) ![Princess Royale Oceanfront Resort](https://images.trvl-media.com/lodging/1000000/30000/22000/21981/b0fe2b94_y.jpg) ### Princess Royale Oceanfront Resort 10/10 Excellent "The entire stay was amazing! We will definitely be booking a future vacation. " [](https://expedia.ca/Ocean-City-Hotels-Princess-Royale-Oceanfront-Resort.h21981.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Montego Bay? ### What is there to see and do in Montego Bay? ### When is the best time to book a hotel with a pool in Montego Bay? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [B&B in Bishopville ](https://www.expedia.ca/Bishopville-Bed-And-Breakfast.d3000440430-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Bishopville Hotels ](https://www.expedia.ca/Bishopville-Hotels.d3000440430.Travel-Guide-Hotels) - [Mountain Hotels in Caine Woods ](https://www.expedia.ca/Caine-Woods-Ocean-City-Hotels-Mountain-Hotels.0-n553248635976482130-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Caine Woods ](https://www.expedia.ca/Caine-Woods-Ocean-City-Hotels-Pet-Friendly-Hotel.0-n553248635976482130-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - 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