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Hotels with Swimming Pool in Stockbridge, Massachusetts
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Our top choices for Stockbridge hotels with a pool
8.8 out of 10, Excellent, (1001)
"Old time charm and hot tub under the stars"
Lori
The price is P8,808
P12,463 total
includes taxes & fees
Jan 14 - Jan 15, 2026
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 P22,427
P27,130 total
includes taxes & fees
Jan 5 - Jan 6, 2026
9.8 out of 10, Exceptional, (13)
"New hotel very nice"
joel
The price is P7,927
P8,855 total
includes taxes & fees
Jan 4 - Jan 5, 2026
9.6 out of 10, Exceptional, (15)
"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 P12,449
P15,873 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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, (710)
"Great hospitality "
regina maria
The price is P6,283
P7,018 total
includes taxes & fees
Jan 4 - Jan 5, 2026
9.2 out of 10, Wonderful, (1005)
"Friendly staff, very clean room and super comfy bed"
Linda
The price is P4,941
P5,520 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (995)
"Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful . "
Dwight
The price is P5,444
P6,080 total
includes taxes & fees
Dec 23 - Dec 24
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
Edward
The price is P6,154
P6,874 total
includes taxes & fees
Jan 4 - Jan 5, 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.
Top Stockbridge Hotel Reviews
The Red Lion Inn
10/10 Excellent
