Find Ski Hotels in Pittsfield, MA
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Our top choices for Pittsfield ski hotels
9.2 out of 10, Wonderful, (887)
"Clean, Great Staff, Quiet"
john
The price is NT$2,235
NT$2,642 total
includes taxes & fees
Jan 19 - 2026/1/20
9.0 out of 10, Wonderful, (810)
"Yes it was clean & staff was very polite. "
Barbara L.
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, (713)
"We stay here every year and it never disappoints "
Elizabeth
The price is NT$3,206
NT$3,581 total
includes taxes & fees
Jan 28 - 2026/1/29
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 NT$2,401
NT$2,682 total
includes taxes & fees
Jan 4 - 2026/1/5
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (1003)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
Clare
The price is NT$2,772
NT$3,097 total
includes taxes & fees
Jan 3 - 2026/1/4
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
MARIA J
The price is NT$2,703
NT$3,019 total
includes taxes & fees
Dec 30 - Dec 31
8.6 out of 10, Excellent, (348)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
Lynn
The price is NT$2,955
NT$3,301 total
includes taxes & fees
Dec 30 - Dec 31
9.0 out of 10, Wonderful, (796)
"Spacious room and loved pool and hot tub!"
Deanna
The price is NT$3,102
NT$4,167 total
includes taxes & fees
Jan 11 - 2026/1/12
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 Pittsfield Hotel Reviews
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
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- Frelinghuysen Morris House and Studio
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