Photo by Robin/Loving Life
Find Winery Hotels in Canaan, NY
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Canaan Winery Hotels
Top Canaan Winery Hotels
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
9.0 out of 10, Wonderful, (1002)
"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!"
Elisabeth
The price is SAR 380
SAR 424 total
includes taxes & fees
16 Dec - 17 Dec
voco James Newbury Hudson Valley by IHG
Coxsackie
9.2 out of 10, Wonderful, (327)
"Beautiful room and very clean"
Mariam
The price is SAR 492
SAR 531 total
includes taxes & fees
4 Jan - 5 January 2026
East Rock Inn
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."
Laura
The price is SAR 491
SAR 549 total
includes taxes & fees
4 Jan - 5 January 2026
Berkshire Valley Inn
Williamstown
9.2 out of 10, Wonderful, (564)
"We had a short but pleasant stay. "
Scott
The price is SAR 503
SAR 562 total
includes taxes & fees
8 Dec - 9 Dec
All comforts of home
Hudson
9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
Georgine
The price is SAR 368
SAR 496 total
includes taxes & fees
8 Dec - 9 Dec
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! "
Marisa P.
The price is SAR 399
SAR 531 total
includes taxes & fees
8 Dec - 9 Dec
Brook Farm Inn
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
Christopher
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. "
Kaye S.
The price is SAR 507
SAR 1,396 total
includes taxes & fees
8 Dec - 9 Dec
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 Canaan Hotel Reviews
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
Explore a world of travel with Expedia
Find More Hotels near Canaan
More Accommodation Types in Canaan
- Vacation Homes in New York
- Apartments in New York
- Cottages in New York
- Cabin Rentals in New York
- Condo Rentals in New York
- Motels in New York
- B&B in New York
- Farmstay in New York
- Chalets in New York
- Lodges in New York
- Villas in New York
- Aparthotels in New York
- Guest Houses in New York
- RV Parks in New York
- Resorts in New York
- Inns in New York
- Hostels in New York
- Houseboats in New York
- Castles in New York
- Holiday Park Resorts in New York
- Safari Tentalow in New York
- Condo Resorts in New York
- Country Houses in New York
- Residences in New York
- Ranches in New York
- Treehouses in New York
Hotels near popular Canaan Attractions
- Hotels near Jiminy Peak Mountain Resort
- Hotels near Tanglewood Music Center
- Hotels near Ski Butternut
- Hotels near Catamount Ski Area
- Hotels near National Shrine of the Divine Mercy
- Hotels near Hudson River
- Hotels near Bousquet Ski Area
- Hotels near Mount Greylock
- Hotels near Lee Premium Outlets
- Hotels near Norman Rockwell Museum
Canaan Hotels by Star Rating
Explore more hotels
- Hampton Inn & Suites Berkshires-Lenox
- Holiday Inn Express Hotel & Suites Great Barrington by IHG
- Best Western Plus Berkshire Hills Inn & Suites
- Hotel On North
- Courtyard by Marriott Lenox Berkshires
- Hampton Inn & Suites Albany-East Greenbush
- Huttopia Berkshires
- voco James Newbury Hudson Valley by IHG
- Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
- Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG
- Holiday Inn Express Hotel & Suites West Coxsackie by IHG
- Quality Inn
- Hilton Garden Inn Lenox Pittsfield
- Jiminy Peak Mountain Resort
- Monument Mountain Motel
- Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
- The Ponds at Foxhollow
- Quality Inn
- Prospect Berkshires
- Howard Johnson by Wyndham Lenox