Find Winery Hotels in West Stockbridge, MA

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on West Stockbridge Winery Hotels

Top West Stockbridge Winery Hotels

Premium bedding, memory foam beds, individually decorated
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 SAR 446
SAR 517 total
includes taxes & fees
5 Jan - 6 January 2026
Nautical Nest
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, (1004)
"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
23 Dec - 24 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 491
SAR 549 total
includes taxes & fees
4 Jan - 5 January 2026
East Rock Inn
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 616
SAR 696 total
includes taxes & fees
18 Dec - 19 Dec
Wm. Farmer & Sons
Exterior
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 SAR 503
SAR 562 total
includes taxes & fees
18 Dec - 19 Dec
Berkshire Valley Inn
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
22 Dec - 23 Dec
All comforts of home
Outdoor dining
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 SAR 547
SAR 1,416 total
includes taxes & fees
10 Dec - 11 Dec
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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 531 total
includes taxes & fees
22 Dec - 23 Dec
All the comforts of home
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is SAR 601
SAR 1,505 total
includes taxes & fees
8 Jan - 9 January 2026
Historic Berkshires Home Near Tanglewood, Trails & Wineries
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
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.
View all properties

Top West Stockbridge Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The room was spacious and clean, the jetted tub was a nice treat, and the breakfast was fresh. "
Christina 2-night trip
Posted 6 days ago
The Yankee, Trademark Collection by Wyndham

Explore a world of travel with Expedia