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

Best Resorts in Canaan

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Check prices for these dates

Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25
In one month
Nov 6 - Nov 8
In two months
Dec 4 - Dec 6
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)
"Very nice hotel."
United States
Erdem
$194 nightly
The price is $217
Nov 4 - Nov 5
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, (1,000 reviews)
"Friendly staff. Good location."
United States
Joe
$93 nightly
The price is $104
Nov 1 - Nov 2
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, (515 reviews)
"Perfect as I was just needing a place to stay overnight."
United States
Kris
$75 nightly
The price is $84
Oct 6 - Oct 7
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, (1,007 reviews)
"The room was spacious, clean and comfortable. I will definitely stay there again."
United States
William
$106 nightly
The price is $118
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A red building with a sign reading "Shaker Mill Inn."

5. 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
$138 nightly
The price is $151
Nov 1 - Nov 2
Total with taxes and fees
Shaker Mill Inn
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

6. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (920 reviews)
"Clean, big rooms!"
United States
Mark
$79 nightly
The price is $88
Oct 6 - Oct 7
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A group of people performing yoga in an outdoor setting with grass and trees.

7. Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 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
Oct 6 - Oct 7
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

8. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (662 reviews)
"Nice hotel."
United States
Tracy
$126 nightly
The price is $140
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
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, (1,173 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
$115 nightly
The price is $128
Nov 4 - Nov 5
Total with taxes and fees
Berkshire Mountain Lodge
A wooden deck with white railings and hanging flower baskets.

10. Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (247 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
Oct 6 - Oct 7
Total with taxes and fees
Chatham Travel Lodge
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)
"Breakfast was great"
United States
Thomas
$115 nightly
The price is $128
Nov 4 - Nov 5
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (227 reviews)
"Most helpful staff, very clean and best breakfast around"
United States
Sheldon
$103 nightly
The price is $115
Nov 4 - Nov 5
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

13. 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
$128 nightly
The price is $143
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
A building entrance with a large planter with purple flowers and a small tree.

14. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (935 reviews)
"Great place!"
United States
Lawrence
$127 nightly
The price is $141
Nov 1 - Nov 2
Total with taxes and fees
Hotel On North
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

15. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,031 reviews)
"A very good place to stay"
United States
Madhavi R
$136 nightly
The price is $152
Nov 1 - Nov 2
Total with taxes and fees
Berkshires Untold
A snow-covered outdoor area with a patio, seating, and a covered dining area.

16. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
$160 nightly
The price is $179
Oct 27 - Oct 28
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

17. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,004 reviews)
"Very nice stay"
United States
Christine
$93 nightly
The price is $103
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Lee - Lenox South
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

18. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (422 reviews)
"Large, clean, comfortable suite."
United States
Rena
$99 nightly
The price is $111
Oct 7 - Oct 8
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.

19. 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, (15 reviews)
"Place was nice, decent value, comfy and cozy. Would stay again."
United States
John
$239 nightly
The price is $242
Oct 6 - Oct 7
Total with taxes and fees
NEW RENO - Historic Loft w/views of the Berkshires
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

20. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (932 reviews)
"Very well maintained and clean for an older looking property. I stayed here twice now."
United States
Kristina
$78 nightly
The price is $87
Nov 4 - Nov 5
Total with taxes and fees
Berkshire Inn
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

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"great room and great area"
Ramon 2-night trip
Posted less than an hour ago
Jiminy Peak Mountain Resort

Find out more about Canaan

Canaan Resorts information

Number of reviews
9,363
Accommodation
8 Resorts
Lowest Price
$76
Highest Price
$242

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. Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out - Ski resort, 5-minute walk from Jiminy Peak Mountain Resort. 12.9 mi (20.7 km) from Canaan. Access to ski-in/ski-out access, a fitness center, and an indoor pool.
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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