A red bridge over a river with snow patches and dry grass.

Best Resorts in Canaan

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Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20
No exact matches found, but these alternatives could be just right

Recommended hotels in Canaan

A modern hotel lobby with seating areas, tables, and a reception desk.

1. 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, (843 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
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

2. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,003 reviews)
"good location, friendly helpful staff"
United States
Scott Patterson
$77 nightly
The price is $86
Nov 15 - Nov 16
Total with taxes and fees
Quality Inn Great Barrington
A covered porch with white railings and rocking chairs.

3. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (452 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
$105 nightly
The price is $121
Oct 25 - Oct 26
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

4. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (928 reviews)
"Super clean and cozy and safe"
United States
Andrea
$67 nightly
The price is $74
Nov 1 - Nov 2
Total with taxes and fees
Monument Mountain Motel
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

5. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (817 reviews)
"Nice view and location for fall color."
United States
Md
$144 nightly
The price is $160
Nov 2 - Nov 3
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

6. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (243 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
United States
Melanie
$173 nightly
The price is $199
Oct 26 - Oct 27
Total with taxes and fees
Blackberry River Inn
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

7. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (623 reviews)
"Good value for the price"
United States
Ramakrishnan
$79 nightly
The price is $88
Oct 25 - Oct 26
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

8. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (286 reviews)
"Super cute, fairly clean and such a lovely breakfast!"
United States
Luis
$160 nightly
The price is $179
Oct 30 - Oct 31
Total with taxes and fees
the Alander
Interior detail

9. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
$182 nightly
The price is $203
Oct 28 - Oct 29
Total with taxes and fees
Wilder House Berkshires
A wooden deck with a swing chair and a bench overlooking a lake.

10. Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (319 reviews)
"Over eight annual visits to this hotel, it has been a wonderful stay each time."
United States
mary
$287 nightly
The price is $330
Nov 22 - Nov 23
Total with taxes and fees
Interlaken Inn & Resort
A large house with a balcony and a grassy yard.

11. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (634 reviews)
"A fine place for a quick overnight trip to the Berkshires."
United States
David
$115 nightly
The price is $128
Oct 25 - Oct 26
Total with taxes and fees
The Little Lion
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

12. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,005 reviews)
"Had a comfortable stay."
United States
Lucinda
$83 nightly
The price is $93
Nov 17 - Nov 18
Total with taxes and fees
Quality Inn Lee - Lenox South
A bedroom with a large bed, a chair, and a window with curtains.

13. The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (155 reviews)
"It’s an exceptional place in every aspect. "
United States
William
$298 nightly
The price is $343
Nov 22 - Nov 23
Total with taxes and fees
The White Hart
A hotel room with a bed, white pillows, a bedside table with a phone, and a wall-mounted TV displaying a scenic sunset.

14. Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,001 reviews)
"It’s a good place to stay for a night, and the staff there are extremely friendly."
United States
Tyler
$82 nightly
The price is $95
Nov 12 - Nov 13
Total with taxes and fees
Days Inn by Wyndham Torrington
A room with a round table and two chairs, a window with a view of trees and a building, and an air conditioning unit.

15. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (707 reviews)
"It was super clean and safe"
United States
Fernando
$65 nightly
The price is $73
Nov 13 - Nov 14
Total with taxes and fees
Econo Lodge Lee - Great Barrington
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

16. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (57 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
United States
Sharon
$118 nightly
The price is $132
Nov 23 - Nov 24
Total with taxes and fees
East Rock Inn
A house with a stone patio and wooden stools.

17. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (148 reviews)
"Beyond amazing, we loved it so much!"
United States
Stacy
$149 nightly
The price is $167
Nov 23 - Nov 24
Total with taxes and fees
Little Cat Lodge
A white two-story house with a front door, windows, and a chimney.

18. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (95 reviews)
"Fabulous inn… wonderful room, but the advertised fireplace was not available for use"
United States
John
$319 nightly
The price is $350
Nov 1 - Nov 2
Total with taxes and fees
The Old Inn On The Green
An outdoor patio with a fire pit, seating, and umbrellas.

19. The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very good, (49 reviews)
"charming cozy stay, staff was awesome!"
United States
Chelsy
$234 nightly
The price is $265
Oct 25 - Oct 26
Total with taxes and fees
The Millerton Inn
A multi-story building with a balcony, a pond with rocks, and a tree.

20. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,003 reviews)
"Nice place to stay"
United States
Michael
$135 nightly
The price is $150
Oct 26 - Oct 27
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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 Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"A"
Shenaz 1-night trip
Posted 2 hours ago
Quality Inn Lee - Lenox South

Find out more about Canaan

Canaan Resorts information

Number of reviews
5,095
Accommodation
4 Resorts
Lowest Price
$73
Highest Price
$350

Frequently asked questions

What is Canaan like for a resort vacation?
You deserve to get away, and a resort is the perfect place to treat yourself to the amenities and services you need for a relaxing time in Canaan. One of the comfortable resorts in the surrounding area might be just what you're looking for, whether you want an amazing pool, shopping possibilities, or fun activities to try.
What's a top resort for my stay in Canaan?
Our highest-rated resorts around Canaan: Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA - 17.2 mi (27.7 km) from Canaan. Features a fitness center. Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA - 17.2 mi (27.7 km) from Canaan. Has a fitness center. July 12-19 2026: Resort with 2 bedrooms and AC in the delightful Berkshires - 17.4 mi (28.1 km) from Canaan. Enjoy the fitness center. Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA - 17.2 mi (27.7 km) from Canaan. Amenities include a fitness center.
What can I do in Canaan?
Housatonic River, Edith Scoville Memorial Sanctuary, and Lawrence Field are a few of the interesting sights to visit. For more to see in the area, you can spend time at Connecticut Railroad Historical Museum or Douglas Library.
What's the seasonal weather like in Canaan?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°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 27.6 mi (44.4 km) away from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 27.8 mi (44.7 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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