TOP Hotels with Swimming Pool in Florida, MA for 2026

Q: What are some accommodation options with pools in Florida?

Blue Vista Motor Lodge : Aparthotel, 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 : Hotel, 6-minute walk from Massachusetts Museum of Contemporary Art. Provides daily, an indoor pool and free self parking. Hotel Downstreet, an Ascend Collection Hotel : Hotel, 1-minute walk from Green Mountain National Forest. Features daily, a seasonal outdoor pool and free self parking. FairBridge Inn Express : Hotel, 1-minute walk from Jiminy Peak Mountain Resort. Features 2 hot tubs, an outdoor pool and 2 outdoor tennis courts. Hotel Vervana, Trademark Collection by Wyndham : Features a health club, an indoor pool and free valet parking.

A forested area with a waterfall cascading over rocks.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Florida Hotels with Swimming Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Florida hotels with a pool

Hotel Downstreet, an Ascend Collection Hotel

North Adams

Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.

₹17,329 total

includes taxes & fees

24 Aug - 25 Aug

Fairfield Inn & Suites by Marriott Williamstown

Williamstown

Swim indoors year-round at this welcoming retreat with an indoor pool, hot tub, and extended pool hours for ultimate relaxation.

₹24,162 total

includes taxes & fees

24 Aug - 25 Aug

The Porches Inn at Mass MoCA

North Adams

Float peacefully day or night at this 24-hour outdoor pool and hot tub sanctuary.

₹27,302 total

includes taxes & fees

17 Aug - 18 Aug

Willows Motel Williamstown

Williamstown

Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.

₹11,169 total

includes taxes & fees

3 Aug - 4 Aug

Cozy Corner Motel

Williamstown

Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.

₹10,709 total

includes taxes & fees

30 Jul - 31 Jul

Hampton Inn Bennington

Bennington

Dive into year-round aquatic bliss at this Bennington retreat with an immaculate indoor pool and thoughtful amenities.

₹19,324 total

includes taxes & fees

16 Aug - 17 Aug

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers

Maple Terrace Motel

Williamstown

Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.

₹14,993 total

includes taxes & fees

9 Aug - 10 Aug

The Springs Motel

New Ashford

Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.

₹14,182 total

includes taxes & fees

28 Jul - 29 Jul

View all properties

Choose what matters most at hotels with a pool in Florida

Breakfast included

4 stars

Top Florida Hotel Reviews

Jiminy Peak Mountain Resort

10/10 Excellent

"Had everything we needed and even more"

Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent

"The lady who checked us in was nice and very helpful, the room was perfectly clean, beds made. Seen a few people staying there with their dogs, the parking lot has alot of spaces available and there's a vending machine for drinks and snacks in the lobby. They also have breakfast between 7:00am-10:00am it's not the best but it's still good and filling!"

Frequently asked questions

What are some accommodation options with pools in Florida?

Blue Vista Motor Lodge: Aparthotel, 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: Hotel, 6-minute walk from Massachusetts Museum of Contemporary Art. Provides daily, an indoor pool and free self parking. Hotel Downstreet, an Ascend Collection Hotel: Hotel, 1-minute walk from Green Mountain National Forest. Features daily, a seasonal outdoor pool and free self parking. FairBridge Inn Express: Hotel, 1-minute walk from Jiminy Peak Mountain Resort. Features 2 hot tubs, an outdoor pool and 2 outdoor tennis courts. Hotel Vervana, Trademark Collection by Wyndham: Features a health club, an indoor pool and free valet parking.

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 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.

Explore a world of travel with Expedia

More ways to book

Book Hotels with Swimming Pool in Florida on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Florida Hotels with Swimming Pool

Our top choices for Florida hotels with a pool

Hotel Downstreet, an Ascend Collection Hotel