Photo by Photo courtesy of Berkshire Visitors Bureau
Find Winery Hotels in The Berkshires, MA
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Our top choices for The Berkshires hotels with winery
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 ￥16,214
￥18,111 total
includes taxes & fees
Jan 5 - Jan 6, 2026
9.4 out of 10, Exceptional, (164)
"Everything was perfect - location and accommodation."
Christopher
9.2 out of 10, Wonderful, (564)
"We had a short but pleasant stay. "
Scott
The price is ￥19,533
￥21,818 total
includes taxes & fees
Jan 4 - Jan 5, 2026
9.4 out of 10, Exceptional, (36)
"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."
Laura
The price is ￥19,274
￥21,529 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is ￥22,765
￥58,391 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/DryerGreat Barrington
The price is ￥70,691
￥88,931 total
includes taxes & fees
Dec 28 - Dec 29
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.Great Barrington
10.0 out of 10, Exceptional, (1)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
Mary R.
The price is ￥53,234
￥91,991 total
includes taxes & fees
Jan 4 - Jan 5, 2026
8.0 out of 10, Very Good, (193)
"Very well kept property, nice restaurant and is in a great area"
Josephine
The price is ￥24,863
￥29,015 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 The Berkshires Hotel Reviews
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
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