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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Canaan vacation rentals

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

1. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is ￥14,169
￥21,982 total
includes taxes & fees
Oct 11 - Oct 12
Cozy 1-bedroom studio in serene Great Barrington with AC
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

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, (54 reviews)
"Clean property, very cute. Also very small. Cable/tv access was challenging, but all on all a good experience"
United States
traci
The price is ￥19,912
￥37,596 total
includes taxes & fees
Oct 12 - Oct 13
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

3. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥29,441
￥69,426 total
includes taxes & fees
Oct 12 - Oct 13
Cheerful 3-bedroom cottage with woodstove
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

4. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥33,375
￥52,755 total
includes taxes & fees
Oct 26 - Oct 27
Home in Great Barrington
A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is ￥21,808
￥37,959 total
includes taxes & fees
Nov 1 - Nov 2
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

6. 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 ￥23,615
￥29,975 total
includes taxes & fees
Oct 8 - Oct 9
The Brooks Motel: Exceptional Suite
A sandy beach with a lake and forest in the background.

7. 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, (5 reviews)
"Amazing apartment! Clean, large, close walk to downtown Great Barrington. Joseph was an incredible host - accurate description, great communication. Will definitely be back!"
United States
Marc R.
The price is ￥32,903
￥51,525 total
includes taxes & fees
Oct 8 - Oct 9
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

8. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (53 reviews)
"Great lake house in the beautiful Berkshires. House looked just like the online pics. Kitchen fully stocked with everything you would need. Lake view & backyard were amazing! Lots of fun using kayaks & canoes."
United States
Rose Angela M.
The price is ￥37,137
￥87,025 total
includes taxes & fees
Oct 23 - Oct 24
Cozy Cottage-Sunset On The Lake
A wooden cabin with a porch, a grill, and a flower planter.

9. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is ￥31,486
￥59,773 total
includes taxes & fees
Oct 6 - Oct 7
Ideal location for summer and winter activities with plenty of outdoor space.
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

10. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is ￥32,001
￥50,043 total
includes taxes & fees
Oct 4 - Oct 5
Leaf-Peeper Paradise in the Berkshires
A living room with a fireplace, two armchairs, a sofa, and a TV.

11. 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, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
The price is ￥26,193
￥33,598 total
includes taxes & fees
Oct 5 - Oct 6
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

12. 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 ￥22,528
￥68,391 total
includes taxes & fees
Oct 4 - Oct 5
Art House 3 Beds Close to Warner Theater
A compact RV kitchen with a stove, sink, and cabinets, a dining area with a bench, and a window with a view of greenery.

13. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
The price is ￥24,747
￥31,174 total
includes taxes & fees
Oct 7 - Oct 8
Cozy Camper tucked into the woods
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

14. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Great Barrington
The price is ￥46,793
￥59,682 total
includes taxes & fees
Oct 4 - Oct 5
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
A two-story house with a front porch, a small balcony, and a white picket fence.

15. 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 ￥21,985
￥66,426 total
includes taxes & fees
Oct 4 - Oct 5
Cozy Modern Farmhouse Private Apt - 3 Beds
A two-story house with a front porch, a small balcony, and a white picket fence.

16. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 reviews)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is ￥14,602
￥56,028 total
includes taxes & fees
Oct 7 - Oct 8
Cozy Attic 10 min to Llitchfield
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 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 ￥31,486
￥54,866 total
includes taxes & fees
Oct 8 - Oct 9
Sweet Cozy Victorian in Housatonic. Close to everything.
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

18. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is ￥37,547
￥93,427 total
includes taxes & fees
Oct 5 - Oct 6
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

19. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (21 reviews)
"It was great!"
United States
Amanda T.
The price is ￥30,658
￥50,309 total
includes taxes & fees
Nov 2 - Nov 3
Pristine Cozy Walkable Downtown 2BR Getaway
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.0 out of 10, Wonderful, (2 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is ￥10,233
￥48,359 total
includes taxes & fees
Oct 5 - Oct 6
Real Estate: Therapy - Lake, Laundry, Love it
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Steven was very helpful and so nice. He went above and beyond to help me find a lost item."
Rachelle 3-night trip
Posted 1 hour ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Canaan

Search for holiday rentals in Canaan on Expedia! You can easily find your home rentals, villas, holiday apartments in Canaan using one of the methods below:

  • View our selection of featured holiday rentals in Canaan
  • Use the map to find apartments and other holiday homes in the Canaan neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Canaan while they last

Look no further and take a look at our great range of rental properties in Canaan!

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?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This vacation home rental outside of Canaan offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, 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 Lawrence Field and Connecticut Railroad Historical Museum.

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.