Title: Book the Best Hotels with POOL in Florida in 2025 | Expedia.ca [Hotels in Florida](https://expedia.ca/Florida-Hotels.d553248634999031091.Travel-Guide-Hotels)[Vacation Rentals in Florida](https://expedia.ca/Florida-Vacation-Rentals.d553248634999031091.Travel-Guide-VacationRentals)[Florida Car Rentals](https://expedia.ca/Car-Rentals-In-Florida.d553248634999031091.Car-Rental-Guide)[Florida Vacation Packages](https://expedia.ca/Florida.d553248634999031091.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/24e6a66c6164d8030df4681f43cd39e6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Chris Addams # Find Hotels with a Pool in Florida, MA from CA $123 ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check availability on Florida Hotels with a Pool Tonight [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-10-06&endDate=2025-10-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-10-07&endDate=2025-10-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Florida Hotels with a Pool ![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/2b2e1d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/137f5231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Tent](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/e9560cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Tent](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/b96863a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Huttopia Berkshires Williamstown 10/10 Exceptional (4) "Perfect place for a relaxing getaway! We loved everything! " CA $137 CA $153 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/52cb5a56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, 1 King Bed, Patio | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/5e670f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, 1 King Bed, Patio | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/d7f7feed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/69831a98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Springs Motel New Ashford 9.2/10 Wonderful (72) "Quiet and quaint place. I have stayed a couple of times." CA $139 CA $153 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/New-Ashford-Hotels-The-Springs-Motel.h95124564.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/439bea3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Studio | Private kitchen](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/0716f688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment, 1 Bedroom, Kitchen](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/0e6d6310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 1 King Bed with Sofa bed, Kitchen | Private kitchen](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/f2112a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Knotty Pine Bennington 9.0/10 Wonderful (2) "Very quiet. Evening staff efficient and helpful upon arrival. Breakfast was posted to start at 7 AM but food and drink was not ready. Left without breakfast. " CA $215 CA $234 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Bennington-Hotels-Knotty-Pine.h119106200.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/7549d558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/4a1f06eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/75e29869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/w1290h860x0y968-0dd10b20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Willows Motel Williamstown Williamstown 9.0/10 Wonderful (957) "Very quaint inn, comfortable beds, very clean. Most cheerful staff and great fresh fruit and variety at breakfast." CA $124 CA $139 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Williamstown-Hotels-Willows-Motel-Williamstown.h1753359.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/caece0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Double Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/53d12ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/af22be9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/44727a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Corner Motel Williamstown 9.2/10 Wonderful (867) "Very nice staff, nice breakfast" CA $104 CA $123 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/3cc5cffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/e8fee166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/d878b297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/d594b2f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn At Quail Run Wilmington 9.0/10 Wonderful (66) "Property was just as described, it was great staying there, outdoors was beautiful." CA $258 CA $284 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Wilmington-Hotels-The-Inn-At-Quail-Run.h1153540.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/42933ea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/a441dd28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/d56bdb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Greenfield Greenfield 8.6/10 Excellent (860) "The rooms were well appointed, the free breakfast was very good, the staff was friendly, and the location was convenient. " CA $224 CA $250 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ![Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/92f285fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/df923dad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/9d6fa2c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/c64cd286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Terrace Motel Williamstown 9.6/10 Exceptional (579) "Excellent place. Bountiful view. " CA $138 CA $154 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/04000126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/a8d66378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/ed219351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/5200a28c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den Dover 9.4/10 Exceptional (16) "So cute and in such a great area! It was a perfect stay" CA $60 CA $363 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-Den.h36778065.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) ![Suite](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/ef2d6927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/9685c82c.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) ### Mountaineer Inn West Dover 8.6/10 Excellent (522) "Easy check in and out. Beautiful location" CA $114 CA $132 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/West-Dover-Hotels-Mountaineer-Inn.h82906124.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=553248634999031091&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Florida Hotel Reviews ![Berkshire Inn](//images.trvl-media.com/lodging/1000000/300000/297200/297173/c3ce1b97_y.jpg) ### Berkshire Inn 10/10 Excellent "Nicely remodeled " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) ![Vacation Village in the Berkshires](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Great!" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Howard Johnson by Wyndham Williamstown](//images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/f5e7ded9_y.jpg) ### Howard Johnson by Wyndham Williamstown 10/10 Excellent "Staff was very nice and room was super clean. Also very comfortable bed! " [](https://expedia.ca/Williamstown-Hotels-Howard-Johnson-By-Wyndham-Williamstown.h1498642.Hotel-Information) ![The Porches Inn at Mass MoCA](//images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "Great place to spend an autumn night." [](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.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 "Great place to stay!" [](https://expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information) ![Hotel Vervana, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/b33626c2_y.jpg) ### Hotel Vervana, Trademark Collection by Wyndham 10/10 Excellent "Friendly staff easy check in accessible to different places" [](https://expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information) ![Best Western Bennington](//images.trvl-media.com/lodging/1000000/20000/16400/16323/5ad1b90e_y.jpg) ### Best Western Bennington 10/10 Excellent "Great stay" [](https://expedia.ca/Bennington-Hotels-Best-Western-Bennington.h16323.Hotel-Information) ![Hampton Inn & Suites Greenfield](//images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6_y.jpg) ### Hampton Inn & Suites Greenfield 10/10 Excellent "Staff friendly and helpful" [](https://expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Totally perfect for mass mocha" [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Florida? > [Blue Vista Motor Lodge](https://www.expedia.ca/North-Adams-Hotels-Blue-Vista-Motor-Lodge.h84362148.Hotel-Information): Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. [Vacation Village in the Berkshires](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information): Features free self parking, an indoor pool, and complimentary wireless internet access. [The Williams Inn](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information): Offers a health club, an indoor pool, and complimentary wired internet access. [Hotel Downstreet, an Ascend Collection Hotel](https://www.expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information): Condo resort, 1-minute walk from Jiminy Peak Mountain Resort. Features 2 restaurants, an outdoor pool, and 2 bars. [Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information): Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. ### What is there to see and do in Florida? > The picturesque setting of Deerfield River and Green Mountain National Forest showcase the area's natural beauty. Discover sights such as Florida Town Hall, Reed Brook Preserve, and Florida Free Library during your stay. ### When is the best time to book a hotel with a pool in Florida? > Taking into account the local weather in Florida is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Florida are January, March, February, and November, with each month seeing an average of 7 inches of snowfall. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in North Adams](https://www.expedia.ca/4Star-North-Adams-Hotels.s40-0-d9137.Travel-Guide-Filter-Hotels) - [Farmstay in Adams](https://www.expedia.ca/Adams-Agritourism.d6005393-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Adams](https://www.expedia.ca/Adams-Apart-Hotels.d6005393-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Adams](https://www.expedia.ca/Adams-Bed-And-Breakfast.d6005393-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Adams](https://www.expedia.ca/Adams-Chalets.d6005393-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Adams](https://www.expedia.ca/Adams-Guest-Houses.d6005393-aaGuestHouses.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Beach-Hotel.0-0-d6005393-tBeachHotel.Travel-Guide-Filter-Hotels) - 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