The Best Hotels with a Pool in Florida, MA from NT$3,092 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

Cozy Corner Motel

Williamstown

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

NT$3,135 total

includes taxes & fees

Jun 9 - Jun 10

Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hideaway Inn Mt. Snow

West Dover

NT$3,092 total

includes taxes & fees

Jun 10 - Jun 11

Hampton Inn Bennington

Bennington

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

NT$5,337 total

includes taxes & fees

Jun 14 - Jun 15

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$6,756 total

includes taxes & fees

Jun 9 - Jun 10

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$4,046 total

includes taxes & fees

Jun 10 - Jun 11

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$4,056 total

includes taxes & fees

Jun 30 - Jul 1

The Springs Motel

New Ashford

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

NT$4,237 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.

NT$5,771 total

includes taxes & fees

Jun 23 - Jun 24

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Choose what matters most at hotels with a pool in Florida

Breakfast included

4 stars

Top Florida Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Spacious and clean room, great location, friendly staff"

Grand Summit Resort, A Vail Resorts Property

4/10 Poor

"I was traveling for work and needed a place to stay for one night while I was in the area. The rooms were very outdated and pretty beat up. There was a deck attached to my room and the door didn’t even lock to the deck. It was very warm outside during my stay as well and the air conditioner in my room seem to be broken and the fan didn’t even work on it either. It said the temperature in the room was 78° so I cracked the window only to be met with the sound of a very loud machine outside for the entirety of the night. There was no parking available when I arrived late back to the hotel from work so I had to park in an overflow lot that required a shuttle to get to. I paid $300 for that experience"

Holiday Inn & Suites Pittsfield-Berkshires by IHG

2/10 Terrible

"The hotel is under construction. This was not mentioned when reservations made. The only available parking was down the street at the bank. The television channels did not come in had to call for assistance. Then tv continued to have issues. On the ceiling and the wall there was dark colored “something” mold? dust? GROSS! Not worth the price."

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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