The Best Hotels with a Pool in Florida, MA from NT$2,935 in 2026

Q: What are some accommodations with pools in Florida?

Blue Vista Motor Lodge : Offers a children's pool, an indoor pool, and free self parking. Vacation Village in the Berkshires : Provides daily, an indoor pool, and free self parking. Hotel Downstreet, an Ascend Collection Hotel : Features a sauna, an outdoor pool, and continental. The Williams Inn : Provides a health club, an indoor pool, and free valet parking. Hotel On North : Features daily, a seasonal outdoor pool, and free self parking.

Check availability on Florida Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

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

Jose

NT$3,500 total

includes taxes & fees

May 28 - May 29

Vacation Village in the Berkshires

Williamstown

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

Ellen

NT$4,524 total

includes taxes & fees

Jun 8 - Jun 9

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.

James

NT$5,807 total

includes taxes & fees

Jun 1 - Jun 2

Knotty Pine

Bennington

Kenneth

NT$4,338 total

includes taxes & fees

Jun 1 - Jun 2

Willows Motel Williamstown

Williamstown

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

Charles

NT$2,938 total

includes taxes & fees

Jun 1 - Jun 2

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.

Kenneth

NT$3,830 total

includes taxes & fees

May 31 - Jun 1

Berkshire Inn

Pittsfield

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

Donald W

NT$3,162 total

includes taxes & fees

May 27 - May 28

Hampton Inn Bennington

Bennington

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

Sarah

NT$5,331 total

includes taxes & fees

Jun 7 - Jun 8

View all properties

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

"Nice place. Had a good stay. First night was awful. Our building smelled heavily of weed. And, our room was next to the walkway which meant we heard alot of noise. Outside of that the guests in the building were noisy, loud hallway conversations, yelling, slamming of doors. I didn't sleep all night. Next day we requested a room change and building management accommodated us immediately and apologized. Pool area is huge and there is a nice hot tub. The ground has other pools that are seasonal. Quite a few grills as well. Very nice place, would recommend and wold visit again."

Hotel Vervana, Trademark Collection by Wyndham

6/10 Okay

"Most importantly, our room was clean, nice, and quiet. No problems within the room, and I thought they offered a pretty nice room configuration for a hotel of their price range. However, outside of the room, the amenities were a little disappointing. The pool was not maintained (to be fair, it might have been too cold to merit that in mid-May). The laundry room did not look great, and the gym was marginally better, but both lacking for a hotel of this price range. Breakfast had hot food and was okay overall, though nothing special. Staff were friendly and mostly helpful for everyday things, but I didn’t feel entirely confident in seeking their assistance. Altogether, a nice room and just okay amenities, and a little expensive for its offerings, in my opinion."

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"I was a bit distressed by the parking lot situation and with the garage and lot all dug up and torn apart it looked horrible. But the staff was super kind and helpful and the room was really nice and I liked everything else about it. I was a bit anxious when I pulled up. It would have been nice to know in advance. But our stay went great. (My dog and me). I would stay there again if I have another dog trial out in that area."

The Porches Inn at Mass MoCA

8/10 Good

"Loved my room, staff were friendly and helpful, and the breakfast included delicious bagels and lox. I hope to return, though I will specifically ask to not stay in the building that houses reception. It’s an historic building so not soundproofed, and I could hear every guest checking in and out, and all the sounds from the kitchen during breakfast hours - it was just a little noisy for me."

Hampton Inn & Suites Greenfield

8/10 Good

"The breakfast buffet was very good with great variety. I also liked pots of hot coffee in the lobby available all day. The only thing I didn’t like was the lack of soundproofing between rooms. Perhaps it was because my room could be an adjoining room, but we could hear everything next door. Our neighbor called to complain about our tv volume, so I guess they could hear everything also."

Grand Summit Resort, A Vail Resorts Property

8/10 Good

"Rooms were very clean, great coffee in the room. The resort(the actual area in general )is in “mud month”. Very few restaurants and stores were open. Not the fault of the resort. Refrigerator needed to be requested. The views were spectacular and the lobby was beautiful "

Frequently asked questions

What are some accommodations with pools in Florida?

Blue Vista Motor Lodge: Offers a children's pool, an indoor pool, and free self parking. Vacation Village in the Berkshires: Provides daily, an indoor pool, and free self parking. Hotel Downstreet, an Ascend Collection Hotel: Features a sauna, an outdoor pool, and continental. The Williams Inn: Provides a health club, an indoor pool, and free valet parking. Hotel On North: Features daily, a seasonal outdoor pool, and free self 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 Monroe State Forest, 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.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Florida Hotels with a Pool