A calm lake with autumn foliage reflecting on the water, surrounded by a forested hillside.

East Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for East 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
8.8 out of 10, Excellent, (10 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is CA $109
CA $164 total
includes taxes & fees
Nov 18 - Nov 19
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, (55 reviews)
"It was a nice stay…worked well for the event we attended in town. The host was very nice to work with"
United States
Roberta S.
The price is CA $154
CA $297 total
includes taxes & fees
Nov 22 - Nov 23
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A wooden cabin interior with a bench, a rug, and a hanging plant.

3. 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, (6 reviews)
The price is CA $147
CA $267 total
includes taxes & fees
Nov 15 - Nov 16
Peaceful and cozy 1 bed 1 bath in quaint Winchester
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

4. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is CA $252
CA $580 total
includes taxes & fees
Nov 18 - Nov 19
Cheerful 3-bedroom cottage with woodstove
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

5. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
The price is CA $306
CA $663 total
includes taxes & fees
Nov 18 - Nov 19
Sharon Retreat w/ Private Yard
A rural property with a wooden barn, a white fence, and a mobile home.

6. 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 CA $204
CA $247 total
includes taxes & fees
Nov 17 - Nov 18
Cozy Camper tucked into the woods
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is CA $227
CA $534 total
includes taxes & fees
Nov 17 - Nov 18
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A cabin with a wooden deck and a stone pathway leading to the entrance.

8. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is CA $285
CA $433 total
includes taxes & fees
Dec 13 - Dec 14
Home in Great Barrington
A two-story house with a porch, surrounded by flowering plants.

9. 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 CA $149
CA $506 total
includes taxes & fees
Nov 18 - Nov 19
Cozy Attic 10 min to Llitchfield
A picnic table in a grassy yard with trees and a fence in the background.

10. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 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 CA $287
CA $406 total
includes taxes & fees
Nov 17 - Nov 18
Leaf-Peeper Paradise in the Berkshires
A room with a bed, a small table, and a chair. There is a window with blinds and a door leading to another room.

11. 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 CA $251
CA $300 total
includes taxes & fees
Nov 13 - Nov 14
The Brooks Motel: Exceptional Suite
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 CA $215
CA $612 total
includes taxes & fees
Nov 16 - Nov 17
Art House 3 Beds Close to Warner Theater
A sandy beach with a lake and forest in the background.

13. 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, (7 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 CA $297
CA $461 total
includes taxes & fees
Nov 15 - Nov 16
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A door with a frosted glass panel featuring a landscape painting, a ceiling fan, and a table with a vase of flowers.

14. 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 CA $200
CA $581 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Modern Farmhouse Private Apt - 3 Beds
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

15. 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)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is CA $248
CA $410 total
includes taxes & fees
Nov 14 - Nov 15
Sweet Cozy Victorian in Housatonic. Close to everything.
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

16. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (22 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 CA $245
CA $400 total
includes taxes & fees
Nov 16 - Nov 17
Pristine Cozy Walkable Downtown 2BR Getaway
A spacious living room with a wooden staircase, a dining area, and a television.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 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 CA $87
CA $409 total
includes taxes & fees
Nov 26 - Nov 27
Real Estate: Therapy - Lake, Laundry, Love it
A cozy outdoor seating area with a fire pit, surrounded by wooden chairs and a stone table, set against a backdrop of a house and dense trees.

18. Spa Cabin with Sauna, Hot Tub and Cold Plunge

Spa Cabin with Sauna, Hot Tub and Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (7 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is CA $475
CA $852 total
includes taxes & fees
Nov 29 - Nov 30
Spa Cabin with Sauna, Hot Tub and Cold Plunge
A triangular-shaped building with a balcony and a wooden picnic table in front.

19. 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, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is CA $207
CA $510 total
includes taxes & fees
Nov 17 - Nov 18
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A stone fire pit surrounded by grass and trees in a wooded area.

20. 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, (80 reviews)
"We very much enjoyed our two week stay in July. The cabin suited our needs in every regard. Our lab was also able to fully relax, whether it was napping on the screen porch or sitting by the fire pit. For those looking to explore the region, the location could not be better situated. Hoping to return over Christmas."
United States
Richard M.
The price is CA $249
CA $495 total
includes taxes & fees
Nov 15 - Nov 16
Ideal location for summer and winter activities with plenty of outdoor space.
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 East Canaan Hotel Reviews

Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

10/10 Excellent
"Todo me pareció bien"
Jester 1-night trip
Posted 2 days ago
Americas Best Value Inn Torrington CT

Find out more about East Canaan

Everything you need to know about East Canaan vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the East Canaan vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect East Canaan vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

East Canaan vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in East Canaan. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A East Canaan vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of East Canaan vacation rentals we have selected for you start as low as CA $164 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on East Canaan rentals

At Expedia, we put the best East Canaan vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top East Canaan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream East Canaan vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around East Canaan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find vacation rentals in East Canaan?

Yes, you can find vacation rentals near well known sights in East Canaan, or you can select a more remote option if you're looking for relaxation. East Canaan is known for its wineries.

What are some of the best vacation rentals that East Canaan has to offer?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: You might want to consider this vacation home rental near East Canaan, which 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 East Canaan?

Expedia has 3 vacation rentals for your stay in East Canaan.

What’s there to see and do in East Canaan?

While exploring the area, visit family-friendly sights like Harney and Sons Tea Tasting Room, or get outside and enjoy nature at Beckley Furnace Industrial Park. In the larger area, you’ll find Land of Nod Vineyard and Winery and Haystack Mountain State Park.

What’s a vacation rental in East Canaan like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in East Canaan. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a family trip.