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

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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
The price is CA $126
CA $141 total
includes taxes & fees
Nov 12 - Nov 13
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
The price is CA $108
CA $120 total
includes taxes & fees
Nov 15 - Nov 16
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
The price is CA $147
CA $169 total
includes taxes & fees
Oct 25 - Oct 26
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, (929 reviews)
"Super clean and cozy and safe"
United States
Andrea
The price is CA $84
CA $94 total
includes taxes & fees
Nov 1 - Nov 2
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
The price is CA $201
CA $225 total
includes taxes & fees
Nov 2 - Nov 3
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
The price is CA $245
CA $282 total
includes taxes & fees
Oct 26 - Oct 27
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
The price is CA $111
CA $124 total
includes taxes & fees
Oct 25 - Oct 26
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
The price is CA $224
CA $251 total
includes taxes & fees
Oct 30 - Oct 31
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
The price is CA $230
CA $256 total
includes taxes & fees
Oct 28 - Oct 29
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
The price is CA $369
CA $425 total
includes taxes & fees
Nov 23 - Nov 24
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
The price is CA $145
CA $162 total
includes taxes & fees
Oct 25 - Oct 26
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
The price is CA $130
CA $145 total
includes taxes & fees
Nov 15 - Nov 16
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
The price is CA $418
CA $480 total
includes taxes & fees
Nov 22 - Nov 23
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
The price is CA $115
CA $133 total
includes taxes & fees
Nov 12 - Nov 13
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
The price is CA $92
CA $102 total
includes taxes & fees
Nov 13 - Nov 14
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
The price is CA $176
CA $197 total
includes taxes & fees
Nov 23 - Nov 24
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
The price is CA $202
CA $227 total
includes taxes & fees
Nov 23 - Nov 24
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
The price is CA $406
CA $490 total
includes taxes & fees
Nov 1 - Nov 2
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
The price is CA $309
CA $350 total
includes taxes & fees
Nov 3 - Nov 4
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
The price is CA $164
CA $210 total
includes taxes & fees
Oct 26 - Oct 27
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

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"A dream to park outside my door! Very simple, clean, and comfortable room. Quiet! Wonderful people and an excellent location. My go to."
Tracy 6-night trip
Posted 1 hour ago
Monument Mountain Motel

Find out more about Canaan

Canaan Resorts information

Number of reviews
5,097
Accommodation
4 Resorts
Lowest Price
CA $94
Highest Price
CA $490

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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