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Search Hotels with Pool in Florida

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Check availability on Florida Hotels with Pool

Our top choices for Florida hotels with a pool

Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (3)
"Really happy with our stay and the way we felt at this hideaway "
United States
Edwin
The price is ฿5,057
฿5,563 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hideaway Inn Mt. Snow
Property grounds
Knotty Pine

Knotty Pine

Knotty Pine
2.5 star property
Bennington
9.0 out of 10, Wonderful, (31)
"The rooms were clean and well maintained. The staff was friendly. It is just a motel. "
United States
Martha
The price is ฿3,463
฿3,774 total
includes taxes & fees
18 Dec - 19 Dec
Knotty Pine
Indoor pool
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (988)
"Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful . "
United States
Dwight
The price is ฿2,966
฿3,312 total
includes taxes & fees
19 Dec - 20 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Gazebo
Cozy Corner Motel

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (887)
"Clean, Great Staff, Quiet"
United States
john
The price is ฿2,352
฿2,776 total
includes taxes & fees
17 Dec - 18 Dec
Cozy Corner Motel
Indoor pool, open 6:00 AM to 10 PM, pool loungers
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1004)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is ฿3,929
฿4,389 total
includes taxes & fees
15 Jan - 16 Jan 2026
Hotel Downstreet, an Ascend Collection Hotel
Exterior
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham
2.5 star property
Bennington
8.2 out of 10, Very good, (1002)
"Great location near historic downtown area, nice rooms. Overall, a very pleasant stay."
United States
Richard
The price is ฿3,184
฿3,471 total
includes taxes & fees
24 Dec - 25 Dec
Hotel Vervana, Trademark Collection by Wyndham
Seasonal outdoor pool
The Springs Motel

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (88)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is ฿3,698
฿4,057 total
includes taxes & fees
17 Dec - 18 Dec
The Springs Motel
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers
Maple Terrace Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (589)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
The price is ฿3,117
฿3,481 total
includes taxes & fees
17 Dec - 18 Dec
Maple Terrace Motel
Outdoor pool
Willows Motel Williamstown

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (994)
"Very friendly staff and fresh fruit at breakfast!"
United States
Justin
The price is ฿2,408
฿2,690 total
includes taxes & fees
17 Dec - 18 Dec
Willows Motel Williamstown
Seasonal outdoor pool
Berkshire Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is ฿2,707
฿3,024 total
includes taxes & fees
17 Dec - 18 Dec
Berkshire Inn
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

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
Amy 2-night trip
Posted 3 months ago
Jiminy Peak Mountain Resort

Frequently asked questions

What are some accommodation options 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: Offers a health club, an indoor pool and complimentary high-speed (wired) Internet access. The Williams Inn: Resort, 2-minute walk from Mount Snow. Provides a full-service spa, an outdoor pool and 2 hot tubs. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features free self parking and an outdoor pool.
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 Hoosac Range, Florida Town Hall and Reed Brook Preserve during your stay.
When is the best time to book a hotel with a pool in Florida?
Taking the local weather in Florida into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Florida are January, March, February and November, with each month seeing an average of 17 cm of snowfall.