Book the Best Hotels with POOL in The Berkshires in 2026

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Our top choices for The Berkshires hotels with a pool

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

1. The Yankee Inn

Lenox

Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.

CA $178 total

includes taxes & fees

Dec 2 - Dec 3

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

2. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.

CA $131 total

includes taxes & fees

Dec 9 - Dec 10

An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.

3. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.

CA $202 total

includes taxes & fees

Nov 11 - Nov 12

An indoor swimming pool with clear blue water, surrounded by windows with a view of trees.

4. Courtyard by Marriott Lenox Berkshires

Lenox

Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness centre.

CA $198 total

includes taxes & fees

Nov 15 - Nov 16

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

5. Berkshire Mountain Lodge

Pittsfield

Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.

CA $153 total

includes taxes & fees

Dec 7 - Dec 8

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

6. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.

CA $253 total

includes taxes & fees

Nov 15 - Nov 16

An indoor swimming pool with lounge chairs, a diving board, and a window with a view of trees.

7. Hampton Inn & Suites Berkshires-Lenox

Lenox

Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.

CA $173 total

includes taxes & fees

Nov 22 - Nov 23

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

8. Hilton Garden Inn Lenox Pittsfield

Pittsfield

Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.

CA $187 total

includes taxes & fees

Nov 15 - Nov 16

A large indoor swimming pool with clear blue water, surrounded by white lounge chairs and a few potted plants.

9. Element by Marriott Lenox Berkshires

Lenox

Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.

CA $213 total

includes taxes & fees

Nov 29 - Nov 30

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

10. Vacation Village in the Berkshires

Williamstown

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

CA $142 total

includes taxes & fees

Nov 11 - Nov 12

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Choose what matters most at hotels with a pool in The Berkshires

Breakfast included

4 stars

Top The Berkshires Hotel Reviews

A large, two-story house with a well-maintained lawn and a fence.

Devonfield Inn B&B

Lee

10/10 Excellent

We stayed at the Devonfield Inn in mid-October during peak foliage season. The hotel is a wonderful historic home built in 1800 with much of its historic character preserved. Our hosts were so welcoming and made us feel at home. The room was very comfortable and breakfast was fantastic. In the morning, we got a special surprise to see a bear on the patio drinking from the fountain and robbing the bird feeder. Overall we highly recommend the Devonfield. We will definitely go back.