Holiday Homes in East Canaan

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Check prices for these dates

Our top choices for East Canaan holiday homes

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is NZ$325
includes taxes & fees
8 Nov - 9 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester

2. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is NZ$728
includes taxes & fees
18 Nov - 19 Nov
Cheerful 3-bedroom cottage with woodstove

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is NZ$487
includes taxes & fees
9 Nov - 10 Nov
Real Estate: Therapy - Lake, Laundry, Love it

4. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is NZ$573
includes taxes & fees
9 Nov - 10 Nov
Home in Great Barrington

5. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is NZ$528
includes taxes & fees
8 Nov - 9 Nov
Leaf-Peeper Paradise in the Berkshires

6. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is NZ$652
includes taxes & fees
9 Nov - 10 Nov
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

7. 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, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is NZ$632
includes taxes & fees
5 Nov - 6 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (5 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 NZ$1,172
includes taxes & fees
16 Nov - 17 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.

9. Maya's Garden House

Maya's Garden House
2.0 star property
Great Barrington
The price is NZ$2,047
includes taxes & fees
18 Nov - 19 Nov
Maya's Garden House

10. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is NZ$499
includes taxes & fees
5 Nov - 6 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.

11. 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, (10 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 NZ$2,203
includes taxes & fees
5 Nov - 6 Nov
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

12. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is NZ$1,067
includes taxes & fees
9 Nov - 10 Nov
Secluded Family Home in Serene Stockbridge Woods

13. Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington

Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington
Great Barrington
The price is NZ$2,268
includes taxes & fees
6 Nov - 7 Nov
Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington

14. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is NZ$1,162
includes taxes & fees
9 Nov - 10 Nov
Chic Barn Style * Fireplace * Near Stissing House

15. 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, (42 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveller
The price is NZ$1,450
includes taxes & fees
1 Dec - 2 Dec
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

16. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is NZ$1,150
includes taxes & fees
10 Nov - 11 Nov
Chic Lakeside Oasis|Near Rhinebeck & Millbrook

17. 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)
"Stayed with a group for Millbrook Horse Trials, we had an amazing weekend at this calm and relaxing home with plenty of beds and amenities! What a treat!"
United States
Marianne R.
The price is NZ$2,426
includes taxes & fees
7 Nov - 8 Nov
A Country Lodge Straight Out of the Pages of a Great Novel

18. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is NZ$2,240
includes taxes & fees
11 Nov - 12 Nov
Beautiful and Private Home Centrally Located in the Berkshires
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.

Learn more about East Canaan

Trip time! Discover the wineries in East Canaan.

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