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
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for East Canaan vacation rentals

Dining

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 AED 516
AED 1,595 total
includes taxes & fees
6 Jul - 7 Jul
Art House 3 Beds Close to Warner Theater
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 AED 474
AED 1,473 total
includes taxes & fees
6 Jul - 7 Jul
Cozy Modern Farmhouse Private Apt - 3 Beds
Exterior

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is AED 397
AED 748 total
includes taxes & fees
6 Jul - 7 Jul
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (18 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AED 744
AED 1,163 total
includes taxes & fees
7 Jul - 8 Jul
Cozy Riverside Berkshires Retreat
Outdoor spa tub

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AED 744
AED 1,639 total
includes taxes & fees
7 Jul - 8 Jul
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Desk, iron/ironing board, WiFi, bed sheets

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 AED 551
AED 699 total
includes taxes & fees
6 Jul - 7 Jul
The Brooks Motel: Exceptional Suite
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 AED 1,469
AED 2,560 total
includes taxes & fees
6 Jul - 7 Jul
Guesthouse Cabin vacation rentals in Berkshire County
Exterior

Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.2 out of 10, Wonderful, (5 reviews)
"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 AED 312
AED 987 total
includes taxes & fees
6 Jul - 7 Jul
Cozy Attic 10 min to Llitchfield
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 AED 740
AED 1,635 total
includes taxes & fees
13 Jul - 14 Jul
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AED 397
AED 1,317 total
includes taxes & fees
16 Jul - 17 Jul
Real Estate: Therapy - Lake, Laundry, Love it
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (33 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is AED 1,058
AED 1,580 total
includes taxes & fees
16 Jul - 17 Jul
Home in Great Barrington
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is AED 959
AED 1,461 total
includes taxes & fees
6 Jul - 7 Jul
Litchfield Retreat, Wineries, Foliage & Skiing
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 871
AED 1,846 total
includes taxes & fees
12 Jul - 13 Jul
Cheerful 3-bedroom cottage with woodstove
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 AED 859
AED 2,041 total
includes taxes & fees
6 Jul - 7 Jul
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is AED 1,326
AED 2,489 total
includes taxes & fees
6 Jul - 7 Jul
Treetop Hideaway in Tyringham
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 AED 1,154
AED 3,076 total
includes taxes & fees
15 Jul - 16 Jul
NEW: Chic Modern Barn Style Home in Fun Area
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, (6 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 AED 2,089
AED 4,894 total
includes taxes & fees
6 Jul - 7 Jul
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
1 bedroom, desk, iron/ironing board, WiFi

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is AED 474
AED 1,473 total
includes taxes & fees
6 Jul - 7 Jul
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
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 AED 3,269
AED 5,319 total
includes taxes & fees
15 Jul - 16 Jul
A Country Lodge Straight Out of the Pages of a Great Novel
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, (39 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is AED 2,384
AED 4,025 total
includes taxes & fees
19 Jul - 20 Jul
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"Desk staff was impressive."
Joseph 1-night trip
Posted 2 hours ago
Quality Inn Lee - Lenox South

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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?

Cozy Riverside Berkshires Retreat: Visitors like this East Canaan vacation home rental. It is located on a river and has a fireplace, a garden, and air-conditioning 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 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 KidsPlay Museum, 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 Infinity Music Hall and Bistro.

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.