Find Winery Hotels in Great Barrington, MA

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Check availability on Great Barrington Winery Hotels

Tonight
4 Dec - 5 Dec
Tomorrow
5 Dec - 6 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Great Barrington Winery Hotels

Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Private kitchen | Mini-fridge, microwave, electric kettle
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 SAR 479
SAR 535 total
includes taxes & fees
18 Dec - 19 Dec
East Rock Inn
Fridge, microwave, oven, stovetop
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 SAR 1,163
SAR 1,471 total
includes taxes & fees
8 Dec - 9 Dec
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Exterior
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, (1001)
"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 SAR 380
SAR 424 total
includes taxes & fees
17 Dec - 18 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Premium bedding, memory foam beds, individually decorated
Nautical Nest

Nautical Nest

2.5 star property
Hudson
9.6 out of 10, Exceptional, (123)
"Very cute, great location in town, nice and quiet"
United States
Michael
The price is SAR 446
SAR 517 total
includes taxes & fees
1 Jan - 2 January 2026
Nautical Nest
Room, 1 King Bed, Balcony, Garden View | Balcony view
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 SAR 615
SAR 695 total
includes taxes & fees
17 Dec - 18 Dec
Wm. Farmer & Sons
Interior
the suite @ barn & bike - private, bucolic, serene setting

the suite @ barn & bike - private, bucolic, serene setting

Red Hook
9.8 out of 10, Exceptional, (14)
"The hosts were great communicators! The space was artistic with a relaxing vibe. Comfortable, quiet and clean. We would love to return for another stay. "
United States
Katherine B.
The price is SAR 559
SAR 710 total
includes taxes & fees
7 Dec - 8 Dec
the suite @ barn & bike - private, bucolic, serene setting
Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, rollaway beds, free WiFi
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Dog Friendly A-Frame in the Berkshires! 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 SAR 547
SAR 1,412 total
includes taxes & fees
8 Dec - 9 Dec
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Property grounds
All comforts of home

All comforts of home

Hudson
9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
United States
Georgine
The price is SAR 368
SAR 496 total
includes taxes & fees
13 Dec - 14 Dec
All comforts of home
Property grounds
All the comforts of home

All the comforts of home

Hudson
9.2 out of 10, Wonderful, (28)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is SAR 399
SAR 530 total
includes taxes & fees
8 Dec - 9 Dec
All the comforts of home
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

Quality Inn

Quality Inn

10/10 Excellent
"clean warm room. breakfast was small but good enough to start the day. coffee was delicious. quiet which was nice and also very close to the town center with shops so that was convenient "
Gisselle 2-night trip
Posted 3 days ago
Quality Inn

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