The Best Hotels with a Pool in Florida, MA from ₩149,659 in 2026

Q: 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 : 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 : Features a health club, an indoor pool, and free valet parking. Hotel On North : Hotel, 5-minute walk from Massachusetts Museum of Contemporary Art. Offers a sauna, an outdoor pool, and continental. The Williams Inn : Resort, 3-minute walk from Mount Snow. Provides a full-service spa, an outdoor pool, and 2 hot tubs.

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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

West Dover

₩152,970 total

includes taxes & fees

Jun 9 - Jun 10

Hampton Inn Bennington

Bennington

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

₩264,058 total

includes taxes & fees

Jun 14 - Jun 15

Seasonal outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas

Hotel Vervana, Trademark Collection by Wyndham

Bennington

Soak up summer relaxation at this downtown hotel with a seasonal outdoor pool paradise.

₩205,011 total

includes taxes & fees

Jul 5 - Jul 6

The Inn At Quail Run

Wilmington

Dive into summer luxury at this guesthouse's seasonal pool, complete with sauna and nearby bay views for a refreshing retreat.

₩334,221 total

includes taxes & fees

Jun 8 - Jun 9

Cozy Corner Motel

Williamstown

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

₩155,097 total

includes taxes & fees

Jun 17 - Jun 18

Knotty Pine

Bennington

₩193,360 total

includes taxes & fees

Jun 10 - Jun 11

The Springs Motel

New Ashford

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

₩209,600 total

includes taxes & fees

Jun 9 - Jun 10

Grand Summit Resort, A Vail Resorts Property

West Dover

Take a plunge in the year-round outdoor pool at this Mount Snow resort, with relaxing hot tubs and spa facilities to rejuvenate.

₩285,498 total

includes taxes & fees

Jun 17 - Jun 18

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Choose what matters most at hotels with a pool in Florida

Breakfast included

4 stars

Top Florida Hotel Reviews

The Porches Inn at Mass MoCA

10/10 Excellent

"Very cool concept- whole street of connecting houses. Great facilities inc free electric charging!! Clean room, great breakfast. Really helpful staff. And perhaps most importantly it’s a short walk to Mass MoCA!"

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Hi, for the most part, my stay was fantastic. The staff were excellent. Breakfast was awesome! The Restaurant and Bar were great! My one negative comment is about the lack of hot water in the morning for me to take a shower. Very disappointing. I am coming back there the next 2 weeks and I hope that the Hot Water situation will be rectified."

Hampton Inn Bennington

6/10 Okay

"I found it annoying that my internet connection was so complicated to set up. Other hotels just have a password code. Easy. I also could not watch any TV without having to join a streaming service. Other hotels offer this for free to watch cable. A manual or directive instructing clientele on paper/ laminated would be helpful as the older generation do not all have smart phones and are lost as we can’t view hotel instructions via phone. The elevator was very loud from my room also. I luckily sleep soundly but the noise would keep someone else awake perhaps"

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: 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: Features a health club, an indoor pool, and free valet parking. Hotel On North: Hotel, 5-minute walk from Massachusetts Museum of Contemporary Art. Offers a sauna, an outdoor pool, and continental. The Williams Inn: Resort, 3-minute walk from Mount Snow. Provides a full-service spa, an outdoor pool, and 2 hot tubs.

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 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.

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