A calm lake with autumn foliage reflecting on the water, surrounded by a forested hillside.

East Canaan Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for East Canaan holiday rentals

Living area

1. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is HK$1,722
HK$2,703 total
includes taxes & fees
24 Aug - 25 Aug
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Property grounds

2. 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 HK$1,937
HK$4,072 total
includes taxes & fees
7 Sept - 8 Sept
Cheerful 3-bedroom cottage with woodstove
Terrace/patio

3. 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
9.4 out of 10, Exceptional, (51 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is HK$988
HK$1,889 total
includes taxes & fees
31 Aug - 1 Sept
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Coffee/tea maker, fridge, microwave, oven

4. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is HK$811
HK$1,213 total
includes taxes & fees
31 Aug - 1 Sept
Cozy 1-bedroom studio in serene Great Barrington with AC
Interior

5. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 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 HK$1,500
HK$2,359 total
includes taxes & fees
20 Sept - 21 Sept
Cozy Riverside Berkshires Retreat
TV, fireplace, printers

6. 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, (7 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$4,439
HK$10,291 total
includes taxes & fees
23 Aug - 24 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
2 bedrooms, free WiFi, bed sheets

7. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is HK$974
HK$1,767 total
includes taxes & fees
30 Aug - 31 Aug
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Interior

8. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$478
HK$2,356 total
includes taxes & fees
13 Sept - 14 Sept
Real Estate: Therapy - Lake, Laundry, Love it
Dining

9. 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$1,835
HK$4,085 total
includes taxes & fees
23 Aug - 24 Aug
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Exterior

10. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 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 HK$716
HK$2,199 total
includes taxes & fees
1 Sept - 2 Sept
Cozy Attic 10 min to Llitchfield
Coffee/tea maker, fridge, microwave, oven

11. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is HK$2,117
HK$3,205 total
includes taxes & fees
24 Aug - 25 Aug
Home in Great Barrington
Coffee/tea maker, fridge, microwave, oven

12. Renovated Downtown Great Barrington House

Renovated Downtown Great Barrington House
Great Barrington
8.0 out of 10, Very good, (2 reviews)
"This is a very nice place to stay. My wife and I both remarked on how comfortable we felt there. A proper home away from home. It was well stocked on all fronts, including the kitchen. And I think what put the finishing touch on was the attention to detail... The towels were large, the bathroom rolls were Charmin Ultrasoft, and there were tissue boxes everywhere you're likely to need them. The hosts seem to work with a service, so you can reach someone with questions immediately, and the hosts...
United States
Anonymous traveller
The price is HK$7,171
HK$12,014 total
includes taxes & fees
23 Aug - 24 Aug
Renovated Downtown Great Barrington House
3 bedrooms, iron/ironing board, WiFi, bed sheets

13. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"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$2,529
HK$4,427 total
includes taxes & fees
31 Aug - 1 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Smart TV, books

14. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is HK$3,166
HK$5,311 total
includes taxes & fees
23 Aug - 24 Aug
Fantastic 2-bedroom house with AC in quaint Hillsdale.
1 bedroom, desk, iron/ironing board, WiFi

15. Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is HK$1,013
HK$3,176 total
includes taxes & fees
23 Aug - 24 Aug
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Smart TV, fireplace

16. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
The price is HK$1,224
HK$2,138 total
includes taxes & fees
21 Sept - 22 Sept
Pristine Cozy Walkable Downtown 2BR Getaway
Dining

17. 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$1,102
HK$3,404 total
includes taxes & fees
2 Sept - 3 Sept
Art House 3 Beds Close to Warner Theater
Coffee/tea maker, fridge, microwave, oven

18. 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, (15 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$6,978
HK$11,548 total
includes taxes & fees
31 Aug - 1 Sept
A Country Lodge Straight Out of the Pages of a Great Novel
Outdoor spa tub

19. 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, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,270
HK$3,127 total
includes taxes & fees
25 Aug - 26 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
TV

20. 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 HK$2,212
HK$4,568 total
includes taxes & fees
21 Sept - 22 Sept
Treetop Hideaway in Tyringham
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

Little Cat Lodge

Little Cat Lodge

10/10 Excellent
"We booked during the weekday and the issue was the restaurant on the property isn’t open Monday, Tuesday and Wednesday. So you will need a car to find food. However, we are from NYC and don’t drive. We ordered from a local Greek Pizzeria through DoorDash. It took two hours for delivery. It’s quiet during the weekdays but just book on weekends so you can eat. Otherwise the property is well kept. We loved the pool and the sauna."
P. E. 2-night trip
Posted 5 hours ago
Little Cat Lodge

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 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?

Cozy Riverside Berkshires Retreat: This holiday home rental outside of East Canaan 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 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 KidsPlay Museum, 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 Campbell Falls 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.