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Our top choices for Stockbridge ski hotels
8.8 out of 10, Excellent, (1001)
"Old time charm and hot tub under the stars"
Lori
The price is 3.947.250 ₫
5.584.832 ₫ total
includes taxes & fees
14 Jan - 15 Jan 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 10.050.225 ₫
12.157.914 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
8.6 out of 10, Excellent, (1000)
"Very friendly and good Breakfast."
Jesse
The price is 2.460.768 ₫
2.748.679 ₫ total
includes taxes & fees
22 Dec - 23 Dec
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
Robert
The price is 3.079.908 ₫
3.378.659 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
9.0 out of 10, Wonderful, (1003)
"Room was clean and the staff was super friendly and helpful!"
Ethan
The price is 2.639.395 ₫
2.948.203 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
9.2 out of 10, Wonderful, (1001)
"Friendly staff, very clean room and super comfy bed"
Linda
The price is 2.214.407 ₫
2.473.492 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very good, (992)
"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 2.439.400 ₫
2.724.810 ₫ total
includes taxes & fees
24 Dec - 25 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, (708)
"Great hospitality "
regina maria
The price is 2.815.705 ₫
3.145.142 ₫ total
includes taxes & fees
4 Jan - 5 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.