East Canaan Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for East Canaan vacation rentals

Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Apartment in Torrington

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
9.6 out of 10, Exceptional, (4)
"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 ￥13,935
￥53,477 total
includes taxes & fees
Dec 30 - Dec 31
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Property grounds
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Apartment in winsted

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
9.2 out of 10, Wonderful, (46)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is ￥13,950
￥26,377 total
includes taxes & fees
Dec 30 - Dec 31
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

Vacation Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is ￥13,856
￥97,195 total
includes taxes & fees
Jan 4 - Jan 5, 2026
CT Gate House Goshen CT, Gate House Goshen CT
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is ￥23,673
￥40,258 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Home in Great Barrington
Exterior
Cozy Modern Farmhouse Private Apt - 3 Beds

Apartment in Torrington

Cozy Modern Farmhouse Private Apt - 3 Beds
10.0 out of 10, Exceptional, (4)
"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 ￥17,849
￥59,614 total
includes taxes & fees
Dec 30 - Dec 31
Cozy Modern Farmhouse Private Apt - 3 Beds
Fridge, microwave, oven, stovetop
Charming apartment 7 minute walk to downtown

Apartment in Torrington

Charming apartment 7 minute walk to downtown
10.0 out of 10, Exceptional, (16)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
The price is ￥22,405
￥40,484 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Charming apartment 7 minute walk to downtown
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,828
￥58,553 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Exterior detail
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Apartment in Torrington

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
10.0 out of 10, Exceptional, (1)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is ￥19,102
￥61,291 total
includes taxes & fees
Dec 30 - Dec 31
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Vacation Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is ￥25,083
￥61,421 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Dining
Guesthouse Cabin vacation rentals in Berkshire County

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is ￥61,532
￥105,633 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Guesthouse Cabin vacation rentals in Berkshire County
TV, offices
The Brooks Motel: Exceptional Suite

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is ￥24,895
￥31,390 total
includes taxes & fees
Dec 31 - Jan 1, 2026
The Brooks Motel: Exceptional Suite
Fridge, microwave, oven, stovetop
The Birdsong Apt. | Game Room & Fire Pit

Apartment in Winchester

The Birdsong Apt. | Game Room & Fire Pit
2.0 star property
The price is ￥28,183
￥62,550 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Birdsong Apt. | Game Room & Fire Pit
Game room
Family Ski Getaway in the Berkshires

Vacation Home in Great Barrington

Family Ski Getaway in the Berkshires
9.4 out of 10, Exceptional, (6)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
United States
Kathy C.
The price is ￥31,705
￥46,607 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Family Ski Getaway in the Berkshires
Property grounds
Cheerful 3-bedroom cottage with woodstove

Vacation Home in Sheffield

Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥37,107
￥78,700 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cheerful 3-bedroom cottage with woodstove
Exterior
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Vacation Home in Goshen

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
2.0 star property
The price is ￥41,491
￥83,060 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Vacation Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (3)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ￥89,057
￥208,608 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Vacation Home in Great Barrington

Great Barrington Get Away
9.4 out of 10, Exceptional, (26)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is ￥48,537
￥86,746 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Great Barrington Get Away
Fridge, microwave, oven, stovetop
Catamount, Zip Line, Private Setting, Book Now!

Vacation Home in Egremont

Catamount, Zip Line, Private Setting, Book Now!
10.0 out of 10, Exceptional, (7)
"This was a very lovely home to stay in for our family, everything you need is in the house (basic things minus food of course) We would definitely book this house again when we visit the Berkshires again."
United States
Jason W.
The price is ￥104,119
￥219,815 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Catamount, Zip Line, Private Setting, Book Now!
Exterior detail
Whispering Estate Guest House - A Romantic Countryside Getaway

Vacation Home in Goshen

Whispering Estate Guest House - A Romantic Countryside Getaway
10.0 out of 10, Exceptional, (5)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is ￥125,256
￥189,841 total
includes taxes & fees
Dec 30 - Dec 31
Whispering Estate Guest House - A Romantic Countryside Getaway
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Vacation Home in Great Barrington

Cozy. Clean. Free bagel shop. 3 Fireplaces.
10.0 out of 10, Exceptional, (1)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is ￥53,234
￥91,991 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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 East Canaan Hotel Reviews

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
Dinh 2-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Find out more about East Canaan

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

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

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

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?

Peace and quiet on the lake: Visitors like this East Canaan vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

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.