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Hotels with Swimming Pools in The Berkshires

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Check availability on The Berkshires Hotels with Swimming Pools

Our top choices for The Berkshires hotels with a pool

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is S$108
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2172)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is S$164
includes taxes & fees
15 Dec - 16 Dec
Vacation Village in the Berkshires

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (804)
"Convenient location, very roomy, well equipped kitchen. "
United States
Carolyn
The price is S$199
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (707)
"Great hospitality "
United States
regina maria
The price is S$154
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (986)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is S$134
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
United States
Joyce
The price is S$261
includes taxes & fees
14 Jan - 15 Jan, 2026
The Red Lion Inn

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is S$149
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Lenox Pittsfield

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (788)
"This place is so peaceful and the staff is always helpful "
United States
Leona
The price is S$171
includes taxes & fees
8 Jan - 9 Jan, 2026
Berkshire Mountain Lodge

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (758)
"Clean room, very courteous staff "
United States
Thomas
The price is S$195
includes taxes & fees
21 Dec - 22 Dec
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1001)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is S$156
includes taxes & fees
4 Jan - 5 Jan, 2026
Hampton Inn & Suites Berkshires-Lenox
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels with pools and free breakfast in The Berkshires

4-star hotels with pools in The Berkshires

Hotels with pools and hot tubs in The Berkshires

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top The Berkshires Hotel Reviews

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