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 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27
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, (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
$184 nightly
The price is $206
Nov 22 - Nov 23
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)
"Room was spacious and clean"
United States
James
$93 nightly
The price is $104
Nov 2 - Nov 3
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, (525 reviews)
"Perfect as I was just needing a place to stay overnight."
United States
Kris
$75 nightly
The price is $84
Oct 28 - Oct 29
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, (1,006 reviews)
"The location was good for our trip."
United States
Basil
$96 nightly
The price is $107
Oct 28 - Oct 29
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, (482 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
$112 nightly
The price is $123
Nov 2 - Nov 3
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, (930 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
$79 nightly
The price is $88
Oct 28 - Oct 29
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 28 - Oct 29
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
A spacious hotel lobby with multiple seating areas, large windows, and a television.

8. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,002 reviews)
"Breakfast was great"
United States
Thomas
$110 nightly
The price is $122
Nov 3 - Nov 4
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

9. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (680 reviews)
"Great stay!"
United States
Vandhana
$126 nightly
The price is $140
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
An indoor swimming pool with clear water, tiled floors, and a blue wall.

10. 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, (247 reviews)
"This a much better Holiday Inn than the one at Saugerties that we went one day before."
United States
Yuguo
$101 nightly
The price is $113
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.

11. Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (253 reviews)
"Great clean, economical place to stay."
United States
Patrick
$112 nightly
The price is $125
Oct 28 - Oct 29
Total with taxes and fees
Chatham Travel Lodge
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

12. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (715 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
Exterior

13. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,233 reviews)
"beautiful location, giant suite room for incredible value"
United States
Michael
$115 nightly
The price is $128
Nov 25 - Nov 26
Total with taxes and fees
Berkshire Mountain Lodge
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

14. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (430 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
$99 nightly
The price is $111
Oct 29 - Oct 30
Total with taxes and fees
The Central Downtown Inn & Suites
A building entrance with a large planter with purple flowers and a small tree.

15. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (966 reviews)
"Big spacious rooms, great bed, great bath."
United States
John
$128 nightly
The price is $143
Nov 8 - Nov 9
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.

16. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,053 reviews)
"A very good place to stay"
United States
Madhavi R
$133 nightly
The price is $149
Nov 3 - Nov 4
Total with taxes and fees
Berkshires Untold
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

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, (1,013 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
$110 nightly
The price is $122
Nov 22 - Nov 23
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (15 reviews)
"Place was nice, decent value, comfy and cozy. Would stay again."
United States
John
$213 nightly
The price is $216
Oct 28 - Oct 29
Total with taxes and fees
NEW RENO - Historic Loft w/views of the Berkshires
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

19. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,006 reviews)
"Perfect for a travel stop-over."
United States
James
$93 nightly
The price is $103
Nov 16 - Nov 17
Total with taxes and fees
Quality Inn Lee - Lenox South
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

20. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (845 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
$90 nightly
The price is $101
Nov 12 - Nov 13
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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

Hotel On North

Hotel On North

10/10 Excellent
"Very large room and bathroom. Had parking easily accessible, very nice and helpful staff."
Gaby 2-night trip
Posted 6 hours ago
Hotel On North

Find out more about Canaan

Canaan Resorts information

Number of reviews
10,972
Accommodation
8 Resorts
Lowest Price
$76
Highest Price
$216

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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