East Canaan Vacation Rentals

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Vacation Rentals in East Canaan

Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Apartment in Torrington

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.
$298 nightly
The price is $342
Dec 8 - Dec 9
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

Vacation Home in Goshen

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.
$627 nightly
The price is $643
Dec 8 - Dec 9
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Exterior
Cozy Modern Farmhouse Private Apt - 3 Beds

Apartment in Torrington

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.
$339 nightly
The price is $390
Dec 8 - Dec 9
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$337 nightly
The price is $376
Dec 8 - Dec 9
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Charming apartment 7 minute walk to downtown

Apartment in Torrington

10.0 out of 10, Exceptional, (15)
"Well equipped, lovely home, extremely clean and comfortable!"
United States
Sally V.
$218 nightly
The price is $247
Dec 10 - Dec 11
Total with taxes and fees
Charming apartment 7 minute walk to downtown
Exterior
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Vacation Home in Sherwood Forest

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.
$351 nightly
The price is $392
Dec 15 - Dec 16
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
TV, offices
The Brooks Motel: Exceptional Suite

Apartment in Hillsdale

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.
$164 nightly
The price is $184
Dec 12 - Dec 13
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
$189 nightly
The price is $211
Dec 8 - Dec 9
Total with taxes and fees
Home in Great Barrington
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Vacation Home in Hillsdale

8.4 out of 10, Very Good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
$461 nightly
The price is $517
Dec 8 - Dec 9
Total with taxes and fees
Perfect House In Hillsdale, Brings Friends & Fam
Dining
Guesthouse Cabin vacation rentals in Berkshire County

Cabin in Sheffield

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.
$640 nightly
The price is $715
Dec 9 - Dec 10
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Vacation Home in Housatonic

10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
$217 nightly
The price is $242
Dec 8 - Dec 9
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Property grounds
Cheerful 3-bedroom cottage with woodstove

Vacation Home in Sheffield

10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$404 nightly
The price is $451
Dec 8 - Dec 9
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
TV, fireplace
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Cabin in Cornwall

10.0 out of 10, Exceptional, (5)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
$448 nightly
The price is $508
Dec 8 - Dec 9
Total with taxes and fees
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Game room
Pet Friendly Riverfront Home in Great Barrington

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (6)
$253 nightly
The price is $283
Dec 8 - Dec 9
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington
2 bedrooms, iron/ironing board, WiFi, bed sheets
Litchfield Retreat, Wineries, Foliage & Skiing

Vacation Home in Torrington

2.0 star property
$321 nightly
The price is $363
Dec 8 - Dec 9
Total with taxes and fees
Litchfield Retreat, Wineries, Foliage & Skiing
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (25)
"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.
$464 nightly
The price is $518
Dec 8 - Dec 9
Total with taxes and fees
Great Barrington Get Away
Exterior
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Vacation Home in Goshen

2.0 star property
$459 nightly
The price is $520
Dec 8 - Dec 9
Total with taxes and fees
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Fridge, microwave, oven, stovetop
Modern Ranch Retreat in Hudson Valley

Vacation Home in Millerton

10.0 out of 10, Exceptional, (4)
"Great communication and a fantastic property! The setting is quiet and short walk to downtown Millerton. The Harlem Valley Rail Trail Line is just down the road which offers excellent opportunities for adventures!"
United States
Scott E.
$486 nightly
The price is $550
Dec 17 - Dec 18
Total with taxes and fees
Modern Ranch Retreat in Hudson Valley
Fridge, microwave, oven, stovetop
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Apartment in Great Barrington

$351 nightly
The price is $392
Dec 8 - Dec 9
Total with taxes and fees
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Vacation Home in Great Barrington

10.0 out of 10, Exceptional, (1)
"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
$1,189 nightly
The price is $1,328
Dec 8 - Dec 9
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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

the Alander

the Alander

10/10 Excellent
"Always a fun stay"
Richard 1-night trip
Posted 2 days ago
the Alander

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit East Canaan in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $283 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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?

Pet Friendly Riverfront Home in Great Barrington: Visitors like this East Canaan vacation home rental. It is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. 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.