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Our top choices for Stockbridge pet-friendly hotels
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
8.6 out of 10, Excellent, (1002)
"Very friendly and good Breakfast."
Jesse
The price is Rp1.271.167
Rp1.419.894 total
includes taxes & fees
2 Jan - 3 Jan 2026
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
Morgan
The price is Rp2.264.085
Rp2.528.983 total
includes taxes & fees
6 Jan - 7 Jan 2026
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 Rp1.480.702
Rp1.653.944 total
includes taxes & fees
3 Jan - 4 Jan 2026
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
Lori
The price is Rp2.518.200
Rp3.562.917 total
includes taxes & fees
14 Jan - 15 Jan 2026
9.6 out of 10, Exceptional, (439)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
Carin
The price is Rp1.878.352
Rp2.060.552 total
includes taxes & fees
6 Jan - 7 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 Rp1.743.266
Rp1.947.229 total
includes taxes & fees
11 Jan - 12 Jan 2026
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington BerkshiresGreat Barrington
7.6 out of 10, Good, (565)
"Excellent location!!"
Abdul Samad
The price is Rp1.257.825
Rp1.405.074 total
includes taxes & fees
28 Jan - 29 Jan 2026
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 Rp4.226.292
Rp5.282.697 total
includes taxes & fees
26 Jan - 27 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.