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Find Winery Hotels in Canaan, NY

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Check availability on Canaan Winery Hotels

Tonight
Dec 8 - Dec 9
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Dec 9 - Dec 10
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Top Canaan Winery Hotels

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, (1003)
"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
$101 nightly
The price is $113
Dec 18 - Dec 19
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Restaurant
voco James Newbury Hudson Valley by IHG

voco James Newbury Hudson Valley by IHG

3.5 star property
Coxsackie
9.2 out of 10, Wonderful, (327)
"Beautiful room and very clean"
United States
Mariam
$131 nightly
The price is $141
Jan 4 - Jan 5, 2026
Total with taxes and fees
voco James Newbury Hudson Valley by IHG
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
$134 nightly
The price is $150
Jan 5 - Jan 6, 2026
Total with taxes and fees
East Rock Inn
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
$134 nightly
The price is $150
Dec 9 - Dec 10
Total with taxes and fees
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
$118 nightly
The price is $132
Dec 9 - Dec 10
Total with taxes and fees
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.
$126 nightly
The price is $141
Dec 9 - Dec 10
Total with taxes and fees
All the comforts of home
Room (King Room) | Iron/ironing board, free WiFi, bed sheets
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
$155 nightly
The price is $172
Jan 5 - Jan 6, 2026
Total with taxes and fees
Gateways Inn & Restaurant
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.
$332 nightly
The price is $372
Dec 10 - Dec 11
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Terrace/patio
Pet-Friendly Hudson Escape w/ Hot Tub

Pet-Friendly Hudson Escape w/ Hot Tub

2.0 star property
Stottville
$303 nightly
The price is $308
Dec 10 - Dec 11
Total with taxes and fees
Pet-Friendly Hudson Escape w/ Hot Tub
Outdoor spa tub
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Valatie
10.0 out of 10, Exceptional, (58)
"Great spot on the lake. Super quiet and relaxing."
United States
vincent m.
$480 nightly
The price is $538
Dec 9 - Dec 10
Total with taxes and fees
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
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 Canaan 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 5 days ago
The Yankee, Trademark Collection by Wyndham

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