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

Canaan Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Canaan vacation rentals

Interior

1. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is SAR 825
SAR 1,294 total
includes taxes & fees
31 Aug - 1 Sep
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Terrace/patio

2. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (50 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is SAR 473
SAR 807 total
includes taxes & fees
19 Aug - 20 Aug
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Desk, iron/ironing board, WiFi, bed sheets

3. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is SAR 563
SAR 723 total
includes taxes & fees
16 Aug - 17 Aug
The Brooks Motel: Exceptional Suite
Property grounds

4. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is SAR 927
SAR 1,950 total
includes taxes & fees
7 Sep - 8 Sep
Cheerful 3-bedroom cottage with woodstove
Coffee/tea maker, fridge, microwave, oven

5. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is SAR 1,034
SAR 1,553 total
includes taxes & fees
25 Aug - 26 Aug
Home in Great Barrington
Interior

6. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is SAR 797
SAR 1,235 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat
Dining

7. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is SAR 528
SAR 1,630 total
includes taxes & fees
1 Sep - 2 Sep
Art House 3 Beds Close to Warner Theater
2 bedrooms, WiFi (free), bed sheets

8. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is SAR 490
SAR 877 total
includes taxes & fees
24 Aug - 25 Aug
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Beach nearby, sun loungers, beach towels

9. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is SAR 773
SAR 1,103 total
includes taxes & fees
13 Sep - 14 Sep
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Exterior

10. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is SAR 359
SAR 1,072 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Attic 10 min to Llitchfield
Exterior

11. Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is SAR 485
SAR 1,266 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Modern Farmhouse Private Apt - 3 Beds
Smart TV, fireplace

12. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
The price is SAR 638
SAR 1,092 total
includes taxes & fees
1 Sep - 2 Sep
Pristine Cozy Walkable Downtown 2BR Getaway
Exterior

13. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (130 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
Gorgeous Mountain Views Retreat: Family & Nature
Interior

14. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is SAR 657
SAR 1,199 total
includes taxes & fees
1 Sep - 2 Sep
Sweet Cozy Victorian in Housatonic. Close to everything.
Smart TV, fireplace, books

15. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (23 reviews)
"Clean, quiet, well stocked studio with everything we needed for our weekend in Kent. Very convenient to town. Highly recommend!"
United States
Joy P.
The price is SAR 622
SAR 802 total
includes taxes & fees
16 Aug - 17 Aug
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Outdoor spa tub

16. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is SAR 645
SAR 1,543 total
includes taxes & fees
19 Aug - 20 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

17. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is SAR 638
SAR 1,535 total
includes taxes & fees
9 Sep - 10 Sep
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
TV, fireplace, books

18. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
10.0 out of 10, Exceptional, (2 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is SAR 847
SAR 2,696 total
includes taxes & fees
19 Aug - 20 Aug
NEW: Chic Modern Barn Style Home in Fun Area
Interior

19. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is SAR 387
SAR 1,313 total
includes taxes & fees
9 Sep - 10 Sep
Real Estate: Therapy - Lake, Laundry, Love it
Smart TV

20. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (4 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is SAR 760
SAR 1,642 total
includes taxes & fees
24 Aug - 25 Aug
stylish Berkshires Retreat
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Canaan Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Clean. Bed too soft but linens pleasant. Comfortable chair in room. Breakfast fine."
Leslie 1-night trip
Posted 18 hours ago
Quality Inn Great Barrington

Frequently asked questions

Are there vacation rentals in Canaan?

Yes, there are vacation rentals close to the most popular local attractions in Canaan, or you can select a more secluded option if you're looking for a relaxing stay. Canaan is known for its restaurants and coffeehouses.

What's the top vacation rental in Canaan?

Cozy Riverside Berkshires Retreat: This vacation home rental outside of Canaan is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Canaan?

Expedia has 5 vacation rentals for your stay in Canaan.

What’s there to see and do in Canaan?

Housatonic River and Edith Scoville Memorial Sanctuary are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Campbell Falls State Park and Lawrence Field.

What’s a vacation rental in Canaan like?

Vacation rentals are private properties you can stay in for a long or short time in Canaan. Vacation rentals offer amenities such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for families.