East Canaan Holiday Rentals

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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for East Canaan holiday rentals

Interior

Pristine, Walkable downtown, Entire 2 Bedroom apartment

Pristine, Walkable downtown, Entire 2 Bedroom apartment
Torrington
10.0 out of 10, Exceptional, (17 reviews)
"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 HK$1,293
HK$2,246 total
includes taxes & fees
2 Apr - 3 Apr
Pristine, Walkable downtown, Entire 2 Bedroom apartment
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"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 HK$3,133
HK$5,504 total
includes taxes & fees
24 Mar - 25 Mar
Guesthouse Cabin vacation rentals in Berkshire County
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (35 reviews)
"Julie was an excellent host. She responded quickly to my questions and provided us with a long list of local restaurants and activities.The house is lovely! It was very clean and had everything that we would need for our stay. We appreciated the big kitchen and the open living room- dining room space. "
United States
Kathleen E.
The price is HK$2,812
HK$5,670 total
includes taxes & fees
23 Mar - 24 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Smart TV, books

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, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is HK$1,255
HK$3,108 total
includes taxes & fees
24 Mar - 25 Mar
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Exterior

Dugway Hideaway Walking Distance to Lime Rock Park

Dugway Hideaway Walking Distance to Lime Rock Park
Salisbury
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
United States
Brig
The price is HK$1,567
HK$2,444 total
includes taxes & fees
30 Mar - 31 Mar
Dugway Hideaway Walking Distance to Lime Rock Park
Dining

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is HK$4,230
HK$6,936 total
includes taxes & fees
28 Mar - 29 Mar
Whispering Estate Guest House - A Romantic Countryside Getaway
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is HK$1,445
HK$2,341 total
includes taxes & fees
30 Mar - 31 Mar
Home in Great Barrington
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is HK$2,069
HK$4,391 total
includes taxes & fees
24 Mar - 25 Mar
Treetop Hideaway in Tyringham
TV, fireplace, printers

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"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 HK$4,434
HK$10,405 total
includes taxes & fees
21 Mar - 22 Mar
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Goshen
10.0 out of 10, Exceptional, (1 review)
"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "
United States
Linda D.
The price is HK$2,076
HK$4,643 total
includes taxes & fees
25 Mar - 26 Mar
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is HK$832
HK$5,041 total
includes taxes & fees
22 Mar - 23 Mar
CT Gate House Goshen CT, Gate House Goshen CT
Dining

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 HK$2,136
HK$4,643 total
includes taxes & fees
30 Mar - 31 Mar
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,857
HK$3,955 total
includes taxes & fees
30 Mar - 31 Mar
Cheerful 3-bedroom cottage with woodstove
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is HK$2,045
HK$3,099 total
includes taxes & fees
22 Mar - 23 Mar
Litchfield Retreat, Wineries, Foliage & Skiing
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,586
HK$2,481 total
includes taxes & fees
24 Mar - 25 Mar
Cozy Riverside Berkshires Retreat
Exterior

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 HK$1,012
HK$3,095 total
includes taxes & fees
31 Mar - 1 Apr
Cozy Modern Farmhouse Private Apt - 3 Beds
Fridge, microwave, oven, stovetop

A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (13 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is HK$6,972
HK$11,467 total
includes taxes & fees
31 Mar - 1 Apr
A Country Lodge Straight Out of the Pages of a Great Novel
TV, offices

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
9.2 out of 10, Wonderful, (5 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is HK$1,238
HK$1,562 total
includes taxes & fees
30 Mar - 31 Mar
The Brooks Motel: Exceptional Suite
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"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 HK$3,133
HK$5,197 total
includes taxes & fees
6 Apr - 7 Apr
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Living area

Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
The price is HK$1,050
HK$3,212 total
includes taxes & fees
22 Mar - 23 Mar
Art House 3 Beds Close to Warner Theater
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 Little Lion

The Little Lion

8/10 Good
"Great location for everything"
Nancy L 3-night trip
Posted 3 days ago
The Little Lion

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
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  • 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 holiday rentals in East Canaan?

Yes, there are holiday rentals close to the most popular sights in East Canaan, or you can select a more secluded option if you're looking for a relaxing stay. East Canaan is known for its wineries.

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

Family Ski Getaway in the Berkshires: This holiday home rental outside of East Canaan 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, as well as a kitchen with a fridge, a stovetop and kitchenware, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in East Canaan?

Expedia has 3 holiday 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 wider area, you’ll find Land of Nod Vineyard and Winery and Haystack Mountain State Park.

What’s a holiday rental in East Canaan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in East Canaan. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips.