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Find Hotels with a Pool in Florida, MA

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Check availability on Florida Hotels with a Pool

Tonight
Nov 27 - Nov 28
Tomorrow
Nov 28 - Nov 29
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Top Florida Hotels with a Pool

Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
  • Outdoor pool
  • Indoor pool
  • Pool umbrellas
8.8 out of 10, Excellent, (2149)
Mountain-view relaxation awaits at the indoor and outdoor pools after exploring Berkshire trails. Families appreciate the children's pool, playground, and game room, while skiers love the direct access to Jiminy Peak slopes.
The price is NT$2,322
NT$2,937 total
includes taxes & fees
Nov 29 - Nov 30
Vacation Village in the Berkshires
Property grounds
Knotty Pine

Knotty Pine

2.5 star property
Bennington
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
9.2 out of 10, Wonderful, (24)
The price is NT$3,448
NT$3,758 total
includes taxes & fees
Dec 29 - Dec 30
Knotty Pine
Seasonal outdoor pool
Farm Road Estate

Farm Road Estate

3.0 star property
West Dover
  • Pool
  • Spa
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
10.0 out of 10, Exceptional, (76)
Pool days become alpine adventures at the seasonal outdoor swimming area of this mountain-view estate. Après-ski relaxation continues with massages, kayaking, and ice skating, while the restaurant serves delicious meals to fuel outdoor explorations.
Farm Road Estate
Indoor pool, open 6:00 AM to 10 PM, sun loungers
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
North Adams
  • Indoor pool
  • Pool loungers
  • Hot tub
8.8 out of 10, Excellent, (1009)
Refreshing waters await in the pristine indoor pool, complemented by a surprisingly warm hot tub for post-exploration relaxation. Stylish rooms with mountain views, a 24-hour fitness center, and peaceful ambiance create a rejuvenating retreat.
The price is NT$3,358
NT$3,751 total
includes taxes & fees
Dec 20 - Dec 21
Hotel Downstreet, an Ascend Collection Hotel
Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Indoor pool
8.0 out of 10, Very Good, (972)
Swimmers splash in the pristine indoor pool from 7 AM to 9 PM, complemented by an on-site health club for complete wellness. Hiking trails and skiing opportunities nearby make this centrally located hotel an ideal family-friendly retreat.
The price is NT$2,799
NT$3,127 total
includes taxes & fees
Nov 29 - Nov 30
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Seasonal outdoor pool
The Springs Motel

The Springs Motel

2.0 star property
New Ashford
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Microwave
9.2 out of 10, Wonderful, (87)
Surrounded by mountain views, the seasonal outdoor pool offers summer relaxation with comfortable lounge chairs and hangout spots. Guests love the well-appointed rooms, friendly staff, and outdoor entertainment areas featuring firepits and charcoal grills.
The price is NT$3,787
NT$4,154 total
includes taxes & fees
Nov 29 - Nov 30
The Springs Motel
Outdoor pool
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3.0 star property
West Dover
  • Outdoor pool
  • 2 hot tubs
8.8 out of 10, Excellent, (242)
Mountain adventures meet aquatic relaxation at this ski-in/ski-out retreat. Swimmers enjoy the refreshing outdoor pool while spa-goers indulge in massages and body wraps at NatureSpa after thrilling days on Mount Snow's slopes.
The price is NT$4,836
NT$5,787 total
includes taxes & fees
Dec 1 - Dec 2
Mount Snow Grand Summit Resort
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
  • Breakfast included
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Business services
9.2 out of 10, Wonderful, (884)
Families splash in the lazy river while adventure seekers prepare for nearby hiking trails and cross-country skiing. This family-run motel balances aquatic fun with mountain recreation, creating perfect days that end with sunset barbecues in the garden.
The price is NT$2,342
NT$2,765 total
includes taxes & fees
Dec 2 - Dec 3
Cozy Corner Motel
Exterior
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 star property
Bennington
  • Pool loungers
8.2 out of 10, Very Good, (1002)
Mountain adventure meets poolside relaxation at this pristine retreat. Seasonal swimming combines with tennis courts and fitness facilities, while nearby skiing, hiking, and kayaking await. Gardens offer peaceful respite after exploring Bennington's museums and churches.
The price is NT$3,251
NT$3,544 total
includes taxes & fees
Dec 4 - Dec 5
Hotel Vervana, Trademark Collection by Wyndham
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.
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Top Florida Hotel Reviews

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

10/10 Excellent
"Staff was friendly, room was very nice and really appreciate the breakfast."
Eileen 1-night trip
Posted 2 days ago
Hampton Inn & Suites Greenfield

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Frequently asked questions

What are some accommodations with pools in Florida?
Blue Vista Motor Lodge: 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: Provides free self parking, an indoor pool, and complimentary wireless internet access. Hotel Downstreet, an Ascend Collection Hotel: Features a health club, an indoor pool, and complimentary wired internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Williams Inn: Offers a sauna, an outdoor pool, and continental.
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, Hoosac Range, and Reed Brook Preserve 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.