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Check availability on Great Barrington Winery Hotels

Our top choices for Great Barrington hotels with winery

Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu
East Rock 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 3.652.368 ₫
4.079.696 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
East Rock Inn
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is 2.668.644 ₫
2.980.876 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Premium bedding, memory-foam beds, individually decorated
Nautical Nest

Nautical Nest

Nautical Nest
2.5 star property
Hudson
9.6 out of 10, Exceptional, (125)
"Very cute, great location in town, nice and quiet"
United States
Michael
The price is 3.131.212 ₫
3.632.206 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Nautical Nest
Room, 1 King Bed, Balcony, Garden View | Egyptian cotton sheets, premium bedding, pillow-top beds, minibar
Wm. Farmer & Sons

Wm. Farmer & Sons

Wm. Farmer & Sons
2.5 star property
Hudson
9.2 out of 10, Wonderful, (73)
"So beautifully preserved building. We had a beautiful room with sitting area overlooking the front of the hotel. Very easy to get to main streets and riverside. Restaurant was wonderful. "
United States
Vivienne
The price is 4.628.026 ₫
5.229.493 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Wm. Farmer & Sons
Front of property
Gateways Inn & Restaurant

Gateways Inn & Restaurant

Gateways Inn & Restaurant
3.0 star property
Lenox
8.0 out of 10, Very good, (192)
"Very well kept property, nice restaurant and is in a great area"
United States
Josephine
The price is 4.048.962 ₫
4.725.138 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Gateways Inn & Restaurant
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.
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Top Great Barrington Hotel Reviews

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