Title: Book the Best Hotels with POOL in Jamaica in 2025 | Expedia.ca [Hotels in Jamaica](https://expedia.ca/Jamaica-Hotels.d184052.Travel-Guide-Hotels)[Vacation Rentals in Jamaica](https://expedia.ca/Jamaica-Vacation-Rentals.d184052.Travel-Guide-VacationRentals)[Flights to Jamaica](https://expedia.ca/Cheap-Flights-To-Jamaica.d184052.Travel-Guide-Flights)[Jamaica Car Rentals](https://expedia.ca/Car-Rentals-In-Jamaica.d184052.Car-Rental-Guide)[Jamaica Vacation Packages](https://expedia.ca/Jamaica.d184052.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/5e96b8e74a3fe03dd3d1f81bf3b2ae7e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Jamaica, VT from CA $97 ![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 Jamaica Hotels with a Pool Tonight [Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=184052&startDate=2025-09-24&endDate=2025-09-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=184052&startDate=2025-09-25&endDate=2025-09-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=184052&startDate=2025-09-26&endDate=2025-09-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=184052&startDate=2025-10-03&endDate=2025-10-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Jamaica Hotels with a Pool ## Our top choices for Jamaica hotels with a pool ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/3b0c7cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/80ab5ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/31952972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/1c3d8a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Upper Pass Lodge at Magic Mountain Londonderry 8.2/10 Very good (665) "If this property was updated it would be a wonderful place to stay but as is it’s like a very old motel. I would not stay there again. " CA $88 CA $97 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Londonderry-Hotels-The-Upper-Pass-Lodge-At-Magic-Mountain.h1445790.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/322811f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/32bcc2b6.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/9000000/8790000/8784400/8784377/776c9b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/dd202f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Brattleboro I-91 Brattleboro 8.6/10 Excellent (691) "This was a nice stay, thanks" CA $202 CA $222 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/2f9ec6a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/1bf7bbfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/8c8403c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/6d2f8f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Black Mountain Inn Brattleboro 7.4/10 Good (465) "Excellent staff!" CA $193 CA $212 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/058b0dfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/707e42f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/e51d292e.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/1000000/850000/845500/845427/2680e185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG Brattleboro 8.8/10 Excellent (1004) "Good room, great breakfast options " CA $234 CA $257 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/w776h446x0y3-b969a7b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/1d2c94d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/96a629e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pointe at Castle Hill Resort Cavendish 8.8/10 Excellent (891) "One day stay all went well" CA $176 CA $201 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/e0c2a7a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/c6f78187.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/fddae827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Equinox Golf Resort & Spa Manchester 7.4/10 Good (532) "Beautiful hotel. So much history. Large pool and hot tub, with spa. Selection of restaurants at the hotel " CA $146 CA $234 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/c09bb59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/dd07686d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/8693102d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/ac7a6ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Gentian Lodge at Magic Mountain Londonderry 9.2/10 Wonderful (108) "Lisa was great!" CA $230 CA $254 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Londonderry-Hotels-Blue-Gentian-Lodge-At-Magic-Mountain.h14586320.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/w3835h2559x0y0-b5950146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/w3835h2559x0y0-24a9373a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/w3835h2558x0y0-ab7af499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn and Suites Manchester Manchester Center 9.6/10 Exceptional (1006) "Excellent hotel!!! " CA $213 CA $234 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/01c7428c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/dfe673e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/7d61f01d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/ef2d6927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountaineer Inn West Dover 8.6/10 Excellent (514) "Clean, beautiful area." CA $134 CA $155 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/West-Dover-Hotels-Mountaineer-Inn.h82906124.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/c8c582d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Guesthouse C](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/309a4723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Guesthouse B | Living area](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/98f6f22e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Guesthouse A](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/102e0e1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aspen At Manchester Manchester Center 8.8/10 Excellent (592) "Very nice hotel. Clean and looked recently remodeled. It was very quiet, allowing me to relax. Will stay here again when in the area." CA $156 CA $186 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Bennington-Hotels-Aspen-At-Manchester.h10254459.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=2025-10-08&endDate=2025-10-09®ionId=184052&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Jamaica Hotel Reviews ![Hampton Inn Brattleboro](//images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Good location and value" [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Hampton Inn and Suites Manchester](//images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg) ### Hampton Inn and Suites Manchester 10/10 Excellent "I want to go back to this Hotel again in the future." [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![The Black Bear Lodge at Stratton Mountain Resort](//images.trvl-media.com/lodging/1000000/810000/800800/800765/a75b732a_y.jpg) ### The Black Bear Lodge at Stratton Mountain Resort 10/10 Excellent "Convenient to " [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Pointe at Castle Hill Resort](//images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Friendly people " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Mount Snow Grand Summit Resort](//images.trvl-media.com/lodging/1000000/670000/663200/663170/effe663b_y.jpg) ### Mount Snow Grand Summit Resort 10/10 Excellent "Absolutely beautiful. Staff is super helpful & polite. Room is very nice, wish it had a mini fridge. " [](https://expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information) ![The Equinox Golf Resort & Spa](//images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg) ### The Equinox Golf Resort & Spa 10/10 Excellent "Beautiful hotel. So much history. Large pool and hot tub, with spa. Selection of restaurants at the hotel " [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Colonial Motel And Spa](//images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "It met my needs" [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Comfort Inn & Suites Brattleboro I-91](//images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg) ### Comfort Inn & Suites Brattleboro I-91 10/10 Excellent "This was a nice stay, thanks" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Kimpton Taconic Hotel by IHG](//images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377_y.jpg) ### Kimpton Taconic Hotel by IHG 10/10 Excellent "Great checkout. Friendliness." [](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Jamaica? > [The Equinox Golf Resort & Spa](https://www.expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information): Features a seasonal outdoor pool, an indoor pool, and 4 restaurants. [Hampton Inn Brattleboro](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information): Offers complimentary wired internet access, an indoor pool, and free self parking. [Hampton Inn and Suites Manchester](https://www.expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information): Provides buffet, an indoor pool, and complimentary wired internet access. [Pointe at Castle Hill Resort](https://www.expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information): Features a full-service spa, an indoor pool, and free self parking. [The Putney Inn](https://www.expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information): Features complimentary bicycles, a seasonal outdoor pool, and a 24-hour fitness center. ### What is there to see and do in Jamaica? > Spend some time experiencing the great outdoors at Green Mountain National Forest and Winhall River. Discover sights such as Jamaica State Park, Ball Mountain Dam, and Hot Glass Works during your stay. ### When is the best time to book a hotel with a pool in Jamaica? > Taking into account the local weather in Jamaica can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 24°F. The snowiest months in Jamaica are January, March, November, and February, with each month seeing an average of 9 inches of snowfall. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in South Londonderry](https://www.expedia.ca/4Star-South-Londonderry-Hotels.s40-0-d184074.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Stratton](https://www.expedia.ca/5Star-Stratton-Hotels.s50-0-d163002.Travel-Guide-Filter-Hotels) - [B&B in Bondville](https://www.expedia.ca/Bondville-Bed-And-Breakfast.d6049474-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Bondville](https://www.expedia.ca/Bondville-Guest-Houses.d6049474-aaGuestHouses.Travel-Guide-Accommodation) - [Luxury Hotels in Bondville](https://www.expedia.ca/Bondville-Hotels-Luxury-Hotel.0-0-d6049474-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Bondville](https://www.expedia.ca/Bondville-Hotels-Shopping-Hotel.0-0-d6049474-tShoppingHotel.Travel-Guide-Filter-Hotels) - 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