A calm lake with reflections of the sky and trees, surrounded by lush greenery and hills.

Best Resorts in Canaan

Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29
No exact matches found, but these alternatives could be just right

Recommended hotels in Canaan

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

1. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (117 reviews)
"We had a very pleasant stay at this. Eautiful country property. Check in was smooth and instructions were easy to follow. Our room, in the main building was well appointed. The bed was super comfortable and the amenities were fine. Breakfast was great! Common areas were lovely and inviting, and the s’mores kits in the lobby were just the thing for an evening around the outdoor fire pit. Highly recommend for anyone seeking a serene country setting."
United States
Jody
$234 nightly
The price is $262
Sep 29 - Sep 30
Total with taxes and fees
Inn at Silver Maple Farm
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

2. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,004 reviews)
"Friendly staff. Good location."
United States
Joe
$106 nightly
The price is $118
Oct 18 - Oct 19
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Outdoor pool

3. Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (514 reviews)
"Perfect as I was just needing a place to stay overnight."
United States
Kris
$67 nightly
The price is $76
Sep 29 - Sep 30
Total with taxes and fees
Berkshire Travel Lodge
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

4. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,016 reviews)
"The room was spacious, clean and comfortable. I will definitely stay there again."
United States
William
$108 nightly
The price is $121
Oct 27 - Oct 28
Total with taxes and fees
The Yankee Inn
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

5. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (917 reviews)
"We were in town for a concert and skeptical at first but when we arrived at our room it was very clean, the front desk was quick and pleasant, would definitely recommend as a nice place to stay!"
United States
COLLEEN
$79 nightly
The price is $88
Sep 29 - Sep 30
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A group of people performing yoga in an outdoor setting with grass and trees.

6. Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The best aspect of this motel is the price. It is very close to the Tanglewood concert space and in West Stockbridge, a quaint town with galleries, a good bookstore, the excellent Turnpark Outdoor Sculpture Garden and "Amici" a nice Italian restaurant, etc."
United States
James
$69 nightly
The price is $76
Sep 29 - Sep 30
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
A wooden deck with white railings and hanging flower baskets.

7. Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (245 reviews)
"I had a very nice stay. The staff was friendly and helpful and my room was clean and comfortable. This hotel was conveniently located for my needs and I’d stay here again. The owner is a lovely lady."
United States
andrew
$112 nightly
The price is $125
Sep 29 - Sep 30
Total with taxes and fees
Chatham Travel Lodge
An indoor swimming pool with clear water, tiled floors, and a blue wall.

8. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (220 reviews)
"Enjoyed the jacuzzi, the comfortable, spacious room, and staff was awesome!"
United States
Susan
$103 nightly
The price is $115
Oct 29 - Oct 30
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

9. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,160 reviews)
"Absolutely wonderful room with many amenities with short drive to Tanglewood and restaurant options."
United States
Jay
$109 nightly
The price is $121
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
A red building with a sign reading "Shaker Mill Inn."

10. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (476 reviews)
"Wonderful place to stay!"
United States
Mervin
$179 nightly
The price is $196
Oct 1 - Oct 2
Total with taxes and fees
Shaker Mill Inn
A spacious hotel lobby with multiple seating areas, large windows, and a television.

11. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,003 reviews)
"Hampton inns are always consistent in quality. The bed was very comfy!"
United States
Larry
$121 nightly
The price is $135
Oct 20 - Oct 21
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

12. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,028 reviews)
"It"s a very nice small Hotel- nicely appointed"
United States
Drue
$160 nightly
The price is $179
Sep 30 - Oct 1
Total with taxes and fees
Berkshires Untold
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

13. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (931 reviews)
"Very well maintained and clean for an older looking property. I stayed here twice now."
United States
Kristina
$79 nightly
The price is $88
Oct 29 - Oct 30
Total with taxes and fees
Berkshire Inn
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

14. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (661 reviews)
"Nice hotel."
United States
Tracy
$141 nightly
The price is $158
Oct 25 - Oct 26
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
Room

15. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,003 reviews)
"Look good for being under constructikn"
United States
Debra
$103 nightly
The price is $115
Oct 29 - Oct 30
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

16. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (710 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
$146 nightly
The price is $163
Oct 25 - Oct 26
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

17. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (416 reviews)
"Large, clean, comfortable suite."
United States
Rena
$99 nightly
The price is $111
Sep 30 - Oct 1
Total with taxes and fees
The Central Downtown Inn & Suites
A spacious kitchen with wooden flooring, a dining area with a table and chairs, a black sofa, and a television mounted on the wall.

18. NEW RENO - Historic Loft w/views of the Berkshires

NEW RENO - Historic Loft w/views of the Berkshires
New Lebanon
9.6 out of 10, Exceptional, (14 reviews)
"Place was nice, decent value, comfy and cozy. Would stay again."
United States
John
$220 nightly
The price is $222
Sep 29 - Sep 30
Total with taxes and fees
NEW RENO - Historic Loft w/views of the Berkshires
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

19. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,006 reviews)
"A very clean and lovely property!"
United States
Ann M
$135 nightly
The price is $151
Oct 29 - Oct 30
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

20. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,009 reviews)
"Very nice stay"
United States
Christine
$110 nightly
The price is $122
Oct 19 - Oct 20
Total with taxes and fees
Quality Inn Lee - Lenox South
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Peter 1-night trip
Posted less than an hour ago
Quality Inn Great Barrington

Find out more about Canaan

Canaan Resorts information

Number of reviews
10,926
Accommodation
13 Resorts
Lowest Price
$76
Highest Price
$262

Frequently asked questions

What can I expect from a resort vacation in Canaan?
You deserve a getaway, and a resort is just the place to indulge in all the services and amenities you need for a relaxing time in Canaan. One of the comfortable resorts in the area could be just what you're searching for, whether you want an amazing pool, shopping possibilities, or activities for the kids.
What's a favorite resort in Canaan?
Our highest-rated resorts around Canaan: In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 12.8 mi (20.5 km) from Canaan. Has ski-in/ski-out access, a fitness center, and a garden. COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 12.7 mi (20.5 km) from Canaan. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers.
What can I do in Canaan?
Queechy Lake, Hollow FIelds Reserve, and Hand Hollow State Forest are a few of the interesting sights to visit. Other attractions in the area include Bates Memorial State Park and Hancock Shaker Village.
What's the weather like in Canaan?
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 the best way to get to and around Canaan?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 8 mi (12.9 km) from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 15.8 mi (25.4 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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