Holiday Homes in East Canaan

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for East Canaan holiday homes

Outdoor dining

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is €248
includes taxes & fees
7 Jun - 8 Jun
Real Estate: Therapy - Lake, Laundry, Love it
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 €340
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 €324
includes taxes & fees
1 Jun - 2 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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 €268
includes taxes & fees
2 Jun - 3 Jun
Cozy Riverside Berkshires Retreat
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (31 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is €308
includes taxes & fees
1 Jun - 2 Jun
Home in Great Barrington
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 €499
includes taxes & fees
1 Jun - 2 Jun
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 €569
includes taxes & fees
1 Jun - 2 Jun
NEW: Chic Modern Barn Style Home in Fun Area
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is €342
includes taxes & fees
2 Jun - 3 Jun
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 €435
includes taxes & fees
1 Jun - 2 Jun
Cheerful 3-bedroom cottage with woodstove
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 €460
includes taxes & fees
4 Jun - 5 Jun
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Fridge, microwave, oven, stovetop

Spacious 4BR Central-Berkshires Home with POOL!

Spacious 4BR Central-Berkshires Home with POOL!
Lee
10.0 out of 10, Exceptional, (3 reviews)
"Home was well situated and very well stocked. Beds were comfortable and house was very clean. Would rent again in the future. Great space for our girls weekend and would be good for extended family as well "
United States
Irma A.
Spacious 4BR Central-Berkshires Home with POOL!
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, (5 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 €1,139
includes taxes & fees
1 Jun - 2 Jun
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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 €732
includes taxes & fees
1 Jun - 2 Jun
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Dining

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is €769
includes taxes & fees
1 Jun - 2 Jun
Whispering Estate Guest House - A Romantic Countryside Getaway
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 €1,256
includes taxes & fees
1 Jun - 2 Jun
A Country Lodge Straight Out of the Pages of a Great Novel
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

Blackberry River Inn

Blackberry River Inn

10/10 Excellent
"What a quaint and charming inn! Our room was quaint and very clean. The staff was excellent. The free breakfast was beyond! Served in a sunroom with white glove service. Very classy. The nin is old and some of the floors squeak. -great value."
Dr Mary 3-night trip
Posted 10 hours ago
Blackberry River Inn

Find out more about East Canaan

East Canaan Holiday Homes information

Number of reviews
172
Accommodation
325 Holiday Homes
Lowest Price
€248
Highest Price
€1,256