The Best Hotels with a Pool in Florida, MA from NT$3,384 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 : 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. Offers 2 restaurants, an outdoor pool, and 2 bars. Hotel Vervana, Trademark Collection by Wyndham : Offers a health club, an indoor pool, and free valet parking.

A forested area with a waterfall cascading over rocks.

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Our top choices for Florida hotels with a pool

Hypo-allergenic bedding, desk, laptop workspace, blackout drapes

Hotel Downstreet, an Ascend Collection Hotel

North Adams

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

NT$6,198 total

includes taxes & fees

Jul 20 - Jul 21

The Porches Inn at Mass MoCA

North Adams

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

NT$9,121 total

includes taxes & fees

Aug 9 - Aug 10

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.

NT$8,216 total

includes taxes & fees

Aug 17 - Aug 18

Hampton Inn Bennington

Bennington

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

NT$6,294 total

includes taxes & fees

Jul 19 - Jul 20

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$5,001 total

includes taxes & fees

Aug 9 - Aug 10

Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

Williamstown

Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.

NT$5,098 total

includes taxes & fees

Aug 3 - Aug 4

Willows Motel Williamstown

Williamstown

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

NT$3,384 total

includes taxes & fees

Jul 30 - Jul 31

Cozy Corner Motel

Williamstown

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

NT$3,444 total

includes taxes & fees

Jul 21 - Jul 22

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Choose what matters most at hotels with a pool in Florida

Breakfast included

4 stars

Top Florida Hotel Reviews

Vacation Village in the Berkshires

8/10 Good

"The AC went out on my last night. That was the killer. But the pool, game room, and everything else was alright."

Willows Motel Williamstown

10/10 Excellent

"The location was perfect for traveling back and forth between Williamstown and North Adams.The room was clean and cozy. Paul is a wonderful host and always had good things to say. His dad was equally nice. The breakfast was amazing and included fresh strawberries, peaches, raspberries, blueberries, dates, walnuts and more . I put most of that on top of yogurt! Bottled water and different juices were served as well. The bathroom was clean, the bed was quite comfortable, and the air conditioner was on spot. The little table and chairs outside every room were a plus. My daughter and I could sit outside w/o feeling we only had our rooms to be in. All in all I would definitely stay there again."

Jiminy Peak Mountain Resort

10/10 Excellent

"Everything about our stay was wonderful We made a last-minute decision just to go up for a night and we were able to use several amenities like the chairlift ride for sightseeing. The pool a few times which was at a very comfortable temperature just to get in and relax We were able to use their locker room to take showers before we left to go home on our trip The room was very clean. The bed was comfortable plenty of pillows to choose from. Every staff member we encountered were very accommodating and friendly"

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: 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. Offers 2 restaurants, an outdoor pool, and 2 bars. Hotel Vervana, Trademark Collection by Wyndham: Offers 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 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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Our top choices for Florida hotels with a pool