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Find Hotels with a Pool in Stockbridge, MA
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Our top choices for Stockbridge hotels with a pool
8.8 out of 10, Excellent, (1003)
"Old time charm and hot tub under the stars"
Lori
The price is NT$4,707
NT$6,660 total
includes taxes & fees
Jan 14 - 2026/1/15
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and ChesterwoodStockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
Robert
The price is NT$11,985
NT$14,498 total
includes taxes & fees
Jan 14 - 2026/1/15
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
Morgan
The price is NT$4,236
NT$4,732 total
includes taxes & fees
Jan 6 - 2026/1/7
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (1000)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
Clare
The price is NT$2,768
NT$3,092 total
includes taxes & fees
Jan 3 - 2026/1/4
9.6 out of 10, Exceptional, (18)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....
"
Laura
The price is NT$7,908
NT$9,885 total
includes taxes & fees
Jan 14 - 2026/1/15
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, (714)
"We stay here every year and it never disappoints "
Elizabeth
The price is NT$3,075
NT$3,435 total
includes taxes & fees
Jan 25 - 2026/1/26
9.2 out of 10, Wonderful, (1004)
"Friendly staff, very clean room and super comfy bed"
Linda
The price is NT$3,174
NT$3,546 total
includes taxes & fees
Jan 11 - 2026/1/12
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
Christine
The price is NT$4,013
NT$4,483 total
includes taxes & fees
Jan 2 - 2026/1/3
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 Stockbridge Hotel Reviews
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
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- Lenox Mountain
- Visit South Lee
- Mission House
- Visit Lenox
- Norman Rockwell Museum
- Lee Premium Outlets
- Bousquet Ski Area
- Visit Great Barrington
- Greenock Country Club
- Pleasant Valley Wilderness Sanctuary
- Charles H. Baldwin & Sons
- Berkshire Botanical Garden
- Visit Monterey
- South Lee Vacations
- Visit Lee
- Visit Housatonic
- National Shrine of the Divine Mercy
- Visit West Stockbridge
- Frelinghuysen Morris House and Studio
- Animagic Museum of Animation