Find Luxury Hotels in Canaan, NY

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Check availability on Canaan Luxury Hotels

Tonight
Feb 23 - Feb 24
Tomorrow
Feb 24 - Feb 25
This weekend
Feb 27 - Mar 1
Next weekend
Mar 6 - Mar 8

Our top choices for Canaan luxury hotels

Breakfast, lunch, dinner served; American cuisine

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 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is NT$9,647
NT$11,641 total
includes taxes & fees
Feb 24 - Feb 25
The Old Inn On The Green
Room #10 Queen's Cottage | Living room | Flat-screen TV

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (136 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Exterior

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is NT$15,625
NT$17,453 total
includes taxes & fees
Feb 25 - Feb 26
33 Main
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is NT$7,553
NT$8,859 total
includes taxes & fees
Feb 24 - Feb 25
The Inn at Stockbridge
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (293 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is NT$4,555
NT$5,342 total
includes taxes & fees
Feb 27 - Feb 28
Lakehouse Inn
Suite, Private Bathroom (RedBird Suite) | View from room

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 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is NT$9,788
NT$11,841 total
includes taxes & fees
Mar 8 - Mar 9
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is NT$6,924
NT$7,734 total
includes taxes & fees
Feb 24 - Feb 25
Hampton Terrace Inn
Terrace/patio

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (358 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is NT$3,226
NT$3,603 total
includes taxes & fees
Feb 24 - Feb 25
The Central Downtown Inn & Suites
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 Canaan Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"Clean, breakfast was a nice option before heading to Butternut mountain nearby "
Kristin 1-night trip
Posted 3 days ago
Quality Inn

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.

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