Photo by William Keller
Stockbridge Hotel Guide - Pet Friendly Hotels in Stockbridge, Massachusetts
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Our top choices for Stockbridge pet-friendly hotels
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
Lori
The price is €180
includes taxes & fees
14 Jan - 15 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
8.6 out of 10, Excellent, (1001)
"Very friendly and good Breakfast."
Jesse
The price is €72
includes taxes & fees
4 Jan - 5 Jan 2026
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
Morgan
The price is €128
includes taxes & fees
5 Jan - 6 Jan 2026
9.6 out of 10, Exceptional, (438)
"Nice place, easy check in"
Robert
The price is €105
includes taxes & fees
5 Jan - 6 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
9.0 out of 10, Wonderful, (1000)
"Room was clean and the staff was super friendly and helpful!"
Ethan
The price is €95
includes taxes & fees
14 Jan - 15 Jan 2026
9.6 out of 10, Exceptional, (16)
"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 €229
includes taxes & fees
4 Jan - 5 Jan 2026
9.0 out of 10, Wonderful, (190)
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
Jenna
The price is €133
includes taxes & fees
28 Dec - 29 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very good, (997)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
Frank
The price is €88
includes taxes & fees
5 Jan - 6 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.
Top Stockbridge Hotel Reviews
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
