East Canaan Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for East Canaan holiday rentals

1 bedroom, iron/ironing board, free WiFi, bed sheets

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
9.2 out of 10, Wonderful, (47 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
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$3,132
HK$5,501 total
includes taxes & fees
17 May - 18 May
Guesthouse Cabin vacation rentals in Berkshire County
Fridge, microwave, oven, stovetop

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$1,855
HK$3,944 total
includes taxes & fees
8 Jun - 9 Jun
Cheerful 3-bedroom cottage with woodstove
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, (37 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is HK$3,124
HK$6,087 total
includes taxes & fees
17 May - 18 May
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)
"Very nice cabin, responsive host."
United States
Nick R.
The price is HK$1,394
HK$3,262 total
includes taxes & fees
1 Jun - 2 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

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, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,142
HK$2,946 total
includes taxes & fees
18 May - 19 May
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is HK$2,043
HK$3,113 total
includes taxes & fees
22 May - 23 May
Litchfield Retreat, Wineries, Foliage & Skiing
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 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$2,192
HK$4,510 total
includes taxes & fees
19 May - 20 May
Treetop Hideaway in Tyringham
Fridge, microwave, oven, stovetop

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 HK$956
HK$3,097 total
includes taxes & fees
19 May - 20 May
Art House 3 Beds Close to Warner Theater
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is HK$1,586
HK$2,479 total
includes taxes & fees
15 May - 16 May
Cozy Riverside Berkshires Retreat
Smart TV, fireplace

Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (18 reviews)
"What a comfortable and welcoming place to stay! Great communication with the hosts, and the space had all the amenities we needed, as well as many thoughtful extra touches. Home was spotless, and tastefully decorated. Quiet neighborhood, and super easy access to downtown. Would absolutely stay here again!"
United States
Kathryn A.
The price is HK$1,370
HK$2,306 total
includes taxes & fees
20 May - 21 May
Pristine Cozy Walkable Downtown 2BR Getaway
Dining

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is HK$4,228
HK$6,901 total
includes taxes & fees
15 May - 16 May
Whispering Estate Guest House - A Romantic Countryside Getaway
Dining

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$1,566
HK$2,427 total
includes taxes & fees
25 May - 26 May
Dugway Hideaway Walking Distance to Lime Rock Park
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$4,453
HK$10,431 total
includes taxes & fees
18 May - 19 May
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Desk, iron/ironing board, WiFi, bed sheets

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$1,237
HK$1,561 total
includes taxes & fees
17 May - 18 May
The Brooks Motel: Exceptional Suite
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$2,035
HK$4,574 total
includes taxes & fees
17 May - 18 May
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
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$1,151
HK$3,326 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Modern Farmhouse Private Apt - 3 Beds
Interior

Modern Victorian Walk to Main Street

Modern Victorian Walk to Main Street
Great Barrington
10.0 out of 10, Exceptional, (27 reviews)
"The house and location both perfect for a girls weekend away! "
United States
karen b.
Modern Victorian Walk to Main Street
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$2,349
HK$4,154 total
includes taxes & fees
22 May - 23 May
Cozy. Clean. Free bagel shop. 3 Fireplaces.
TV, fireplace, books

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
The price is HK$2,074
HK$6,079 total
includes taxes & fees
19 May - 20 May
NEW: Chic Modern Barn Style Home in Fun Area
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

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"We decided to stay at Monument Mountain Motel because it’s on our way to Boston. This is our second time staying here. And I’m sure we’ll use them again."
Mary 1-night trip
Posted 16 hours ago
Monument Mountain Motel

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?

Peace and quiet on the lake: This holiday home rental outside of East Canaan is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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 Infinity Music Hall and Bistro.

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.