The Best Hotels with a Pool in Florida, MA from NT$3,043 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

NT$3,110 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.

NT$4,080 total

includes taxes & fees

Jun 22 - Jun 23

Hampton Inn Bennington

Bennington

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

NT$5,369 total

includes taxes & fees

Jun 14 - Jun 15

Cozy Corner Motel

Williamstown

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

NT$3,149 total

includes taxes & fees

Jun 23 - Jun 24

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.

NT$6,786 total

includes taxes & fees

Jun 14 - Jun 15

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

Maple Terrace Motel

Williamstown

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

NT$4,064 total

includes taxes & fees

Jun 22 - Jun 23

The Nutmeg

Wilmington

Summer river retreats with exclusive seasonal poolside fun from July through September.

NT$6,264 total

includes taxes & fees

Jun 22 - Jun 23

Berkshire Inn

Pittsfield

Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.

NT$3,043 total

includes taxes & fees

Jun 15 - Jun 16

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Choose what matters most at hotels with a pool in Florida

Breakfast included

4 stars

Top Florida Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"They were doing some renovations which made parking an issue but otherwise great place."

Vacation Village in the Berkshires

10/10 Excellent

"This is a big beautful modern condo complex about 20 mins outside Wiilamstown (to the north) or Pittsfield (to the south). Huge swimming pools - one indoors, one out. Beautiful views of the Berkshires. Quiet rural environment. I could hear the frogs singing and the cricketa chirp at night. Excellent value for the money. Friendly staff. I got a one-bdrm condo for the price of a standard hotel. No grocery atores nearby some come with supplies if you plan to cook."

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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