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
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10
No exact matches found, but these alternatives could be just right

Recommended hotels in Canaan

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

1. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
$164 nightly
The price is $184
Dec 3 - Dec 4
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, (1,002 reviews)
"Room was spacious and clean"
United States
James
$93 nightly
The price is $104
Dec 1 - Dec 2
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

3. Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (527 reviews)
"The room was clean and the staff friendly."
United States
Istvan
$76 nightly
The price is $85
Nov 11 - Nov 12
Total with taxes and fees
Berkshire Travel Lodge
Two Adirondack chairs facing a river with a forested hill in the background.

4. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
"What a beautiful stay. Room was so clean ! Great food selection for breakfast."
United States
Stephanie
$113 nightly
The price is $126
Nov 15 - Nov 16
Total with taxes and fees
The Yankee Inn
A hotel room with a bed, two chairs, a small table, and a lamp.

5. 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
$63 nightly
The price is $69
Nov 11 - Nov 12
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Exterior

6. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,268 reviews)
"Excellent stay!!!!"
United States
Susan J
$108 nightly
The price is $120
Dec 10 - Dec 11
Total with taxes and fees
Berkshire Mountain Lodge
A spacious hotel lobby with multiple seating areas, large windows, and a television.

7. 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
$110 nightly
The price is $122
Nov 16 - Nov 17
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (937 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
$79 nightly
The price is $88
Nov 11 - Nov 12
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A red building with a sign reading "Shaker Mill Inn."

9. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (483 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
$145 nightly
The price is $159
Nov 12 - Nov 13
Total with taxes and fees
Shaker Mill Inn
A pool area with chairs and a lifeguard sign.

10. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (689 reviews)
"Great stay!"
United States
Vandhana
$126 nightly
The price is $140
Nov 15 - Nov 16
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

11. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (982 reviews)
"Very nice hotel"
United States
Philip
$112 nightly
The price is $125
Nov 29 - Nov 30
Total with taxes and fees
Hotel On North
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
9.4 out of 10, Exceptional, (258 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
$110 nightly
The price is $123
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A wooden deck with white railings and hanging flower baskets.

13. Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (256 reviews)
"Great clean, economical place to stay."
United States
Patrick
$112 nightly
The price is $125
Nov 11 - Nov 12
Total with taxes and fees
Chatham Travel Lodge
A hotel patio with outdoor seating and a fire pit.

14. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (717 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
$119 nightly
The price is $133
Nov 15 - Nov 16
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
A hotel room with a bed, a television, a wardrobe, and a bathroom visible through an open door.

15. Garden Gables

Garden Gables
4.0 star property
Lenox
10.0 out of 10, Exceptional, (2 reviews)
"Lovely place!"
United States
Eyee
$188 nightly
The price is $210
Nov 23 - Nov 24
Total with taxes and fees
Garden Gables
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

16. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,072 reviews)
"Very nice place beautiful view"
United States
Brian
$118 nightly
The price is $132
Nov 17 - Nov 18
Total with taxes and fees
Berkshires Untold
A lodge with a large building and a dock by a lake, surrounded by forest.

17. 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, (1,002 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
$107 nightly
The price is $120
Dec 6 - Dec 7
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

18. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (51 reviews)
"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"
United States
Francis
$135 nightly
The price is $151
Nov 29 - Nov 30
Total with taxes and fees
Element by Marriott Lenox Berkshires
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
9.4 out of 10, Exceptional, (17 reviews)
"Place was nice, decent value, comfy and cozy. Would stay again."
United States
John
$214 nightly
The price is $215
Nov 30 - Dec 1
Total with taxes and fees
NEW RENO - Historic Loft w/views of the Berkshires
A fenced outdoor area with a pool, lounge chairs, and umbrellas.

20. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (942 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
$79 nightly
The price is $88
Dec 10 - Dec 11
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Great place in walking distance to city center. Excellent customer service and kind, helpful staff. Clean rooms and a full breakfast included."
Kiana 1-night trip
Posted 6 hours ago
Quality Inn Great Barrington

Find out more about Canaan

Canaan Resorts information

Number of reviews
3,477
Accommodation
8 Resorts
Lowest Price
$69
Highest Price
$215

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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