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Find Luxury Hotels in Canaan, NY

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Check availability on Canaan Luxury Hotels

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top Canaan Luxury Hotels

Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is SAR 699
SAR 819 total
includes taxes & fees
12 Dec - 13 Dec
Lakehouse Inn
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is SAR 335
SAR 374 total
includes taxes & fees
8 Dec - 9 Dec
The Central Downtown Inn & Suites
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is SAR 986
SAR 1,157 total
includes taxes & fees
21 Dec - 22 Dec
The Inn at Stockbridge
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished
The Old Inn On The Green

The Old Inn On The Green

4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is SAR 1,145
SAR 1,381 total
includes taxes & fees
8 Dec - 9 Dec
The Old Inn On The Green
Exterior
Hampton Terrace Inn

Hampton Terrace Inn

4.0 star property
Lenox
9.0 out of 10, Wonderful, (43)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is SAR 987
SAR 1,102 total
includes taxes & fees
1 Jan - 2 January 2026
Hampton Terrace Inn
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is SAR 1,602
SAR 1,789 total
includes taxes & fees
7 Jan - 8 January 2026
33 Main
Business center
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is SAR 1,433
SAR 1,734 total
includes taxes & fees
28 Dec - 29 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"We stay here every year and it never disappoints "
Elizabeth 4-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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Frequently asked questions

Are you looking for a luxury hotel for your stay in Canaan?
Expedia can help you get a flight to Pittsfield, MA (PSF-Pittsfield Municipal) airport or Hudson, NY (HCC-Columbia County) airport, and then you can select from a variety of places to stay that will deliver the luxury you seek. Amenities are important when you plan a vacation, so we make it easy to find what you'd like to make your stay special. If you want an upscale hotel that has a spa, an indoor pool, or luxury bedding, Expedia can help you find the best luxury hotel experience that Canaan has to offer. Canaan has some interesting things to see and do including Queechy Lake and Hollow FIelds Reserve, so you might want to take in the local sights during your visit.
When can I expect good weather in Canaan?
Planning for the weather is a good way to make your trip to Canaan relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's there to see and do in Canaan?
Enjoy Canaan and visit Queechy Lake, Hollow FIelds Reserve, and Hand Hollow State Forest. If you have a bit of extra time while you're in the area, you might want to check out Hancock Shaker Village and Tanglewood Music Center.