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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 Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is ¥16,214
¥18,111 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn

Berkshire Valley Inn

Berkshire Valley Inn
2.5 star property
Williamstown
9.2 out of 10, Wonderful, (564)
"We had a short but pleasant stay. "
United States
Scott
The price is ¥19,533
¥21,818 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Berkshire Valley Inn

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
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."
United States
Laura
The price is ¥19,274
¥21,529 total
includes taxes & fees
Jan 26 - Jan 27, 2026
East Rock Inn

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."
United States
Sharon K.
The price is ¥22,765
¥58,391 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

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/Dryer
Great Barrington
The price is ¥70,691
¥88,931 total
includes taxes & fees
Dec 28 - Dec 29
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

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!"
United States
Mary R.
The price is ¥53,234
¥91,991 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Gateways Inn & Restaurant

Gateways Inn & Restaurant
3.0 star property
Lenox
8.0 out of 10, Very Good, (193)
"Very well kept property, nice restaurant and is in a great area"
United States
Josephine
The price is ¥24,863
¥29,015 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Gateways Inn & Restaurant

Nautical Nest

Nautical Nest
2.5 star property
Hudson
9.6 out of 10, Exceptional, (126)
"Very cute, great location in town, nice and quiet"
United States
Michael
The price is ¥18,549
¥21,516 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Nautical Nest

Wm. Farmer & Sons

Wm. Farmer & Sons
2.5 star property
Hudson
9.2 out of 10, Wonderful, (75)
"We had a lovely stay. They upgraded our room & we had the most cozy & charming suite. Would absolutely stsy here again. "
United States
Natalie
The price is ¥24,661
¥27,868 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Wm. Farmer & Sons
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

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