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Hotels with Swimming Pools in The Berkshires
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Our top choices for The Berkshires hotels with a pool
9.2 out of 10, Wonderful, (1002)
"Friendly staff, very clean room and super comfy bed"
Linda
The price is S$108
includes taxes & fees
24 Dec - 25 Dec
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"
Karla
The price is S$164
includes taxes & fees
15 Dec - 16 Dec
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 IHGSouth Lee
9.0 out of 10, Wonderful, (804)
"Convenient location, very roomy, well equipped kitchen.
"
Carolyn
The price is S$199
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
8.8 out of 10, Excellent, (707)
"Great hospitality "
regina maria
The price is S$154
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very good, (986)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
Frank
The price is S$134
includes taxes & fees
17 Dec - 18 Dec
8.8 out of 10, Excellent, (1002)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
Joyce
The price is S$261
includes taxes & fees
14 Jan - 15 Jan, 2026
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
Kristen
The price is S$149
includes taxes & fees
21 Dec - 22 Dec
9.0 out of 10, Wonderful, (788)
"This place is so peaceful and the staff is always helpful "
Leona
The price is S$171
includes taxes & fees
8 Jan - 9 Jan, 2026
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
9.2 out of 10, Wonderful, (1002)
The price is S$108
includes taxes & fees
24 Dec - 25 Dec
4-star hotels with pools in The Berkshires
9.8 out of 10, Exceptional, (99)
The price is S$380
includes taxes & fees
1 Jan - 2 Jan, 2026
Hotels with pools and hot tubs in The Berkshires
9.2 out of 10, Wonderful, (1002)
The price is S$108
includes taxes & fees
24 Dec - 25 Dec
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
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
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