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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 337 Vacation Homes in East Canaan with updated reviews, rates, and availability.

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Exterior

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (151)
"Hi,The views are spectacular, house is spacious and close to skiing. We had a great time staying in this house. We even talked about coming back in warmer weather. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Mountain View Getaway
Outdoor dining

Mountain View Getaway

10.0 out of 10, Exceptional, (51)
"We loved this property!!"
Mountain View Getaway
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (214)
"We enjoyed the privacy and quiet of the location. The house itself is very well kept inside and cozy. "
Peace and quiet on the lake
Lakeside Oasis Just You, The Lake & The View!
Exterior

Lakeside Oasis Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"Perfect location for a peaceful, scenic vacation."
Lakeside Oasis Just You, The Lake & The View!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (25)
"Well located and comfortable "
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
The Race Mountain House
Pool

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (36)
"The property was centrally located for skiing, and was a comfortable stay."
The price is AEDĀ 687
AEDĀ 1,621 total
includes taxes & fees
13 May - 14 May
Cheerful 3-bedroom cottage with woodstove
Perfect Nature Haven In Great Barrington
Exterior

Perfect Nature Haven In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Haven In Great Barrington
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (9)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Exclusive Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Exclusive Estate, Heated Yearround Outdoor Pool
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
The Goshen Glass Chalet
Outdoor dining

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (34)
"Nice and cozy property. The host has been very responsive. "
The Goshen Glass Chalet
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (46)
"There is a game room that provided lots of fun. The linens were luxurious, the kitchen had every utensil. The yard is fenced in, the hot tub was great, we loved it!"
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Large Barn styled vacation home that fits groups with space to spare.
Miscellaneous

Large Barn styled vacation home that fits groups with space to spare.

9.8 out of 10, Exceptional, (60)
"Another excellent experience stay at this house!"
Large Barn styled vacation home that fits groups with space to spare.
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.6 out of 10, Exceptional, (20)
"Our family had a wonderful experience and stay. "
The price is AEDĀ 808
AEDĀ 1,251 total
includes taxes & fees
12 May - 13 May
Home in Great Barrington
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We were taking our first family ski trip and were lucky to stay at this great house which is only 10 minutes from Butternut. Super convenient, very comfortable and the huge kitchen was a perfect place for our family to gather after a day on the slopes. We loved it and would happily return next year!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Lakeside 5-BR Home in Idyllic Berkshires
TV, fireplace, offices

Lakeside 5-BR Home in Idyllic Berkshires

10.0 out of 10, Exceptional, (2)
"Celebrated a birthday with a group of old friends. Great location near Lee. Enjoyed the lake views. Fires inside and outside. Home is well decorated and clean."
Lakeside 5-BR Home in Idyllic Berkshires
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.
Exterior

Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.

10.0 out of 10, Exceptional, (17)
"The Harlem Valley Rail Trail is a great bicycle trail and the house is in the perfect spot to get to it, less than half mile away. The house is clean and perfectly maintained, and the hosts are gracious and accomodating."
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.
Rustic 3bd Lake Front Country Cottage
Smart TV, fireplace, stereo

Rustic 3bd Lake Front Country Cottage

9.4 out of 10, Exceptional, (3)
"Enjoy our hikes and lake front view as well as kayaking around lake. Pretty area."
Rustic 3bd Lake Front Country Cottage
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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Other property types in East Canaan

Lakefront Spring Stunner in New England Just 2 Hours From NYC
Interior

Lakefront Spring Stunner in New England Just 2 Hours From NYC

9.8 out of 10, Exceptional, (68)
"Overall a nice place to visit. A small family who likes the outdoors would enjoy it. "
Lakefront Spring Stunner in New England Just 2 Hours From NYC
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is AEDĀ 437
AEDĀ 570 total
includes taxes & fees
11 May - 12 May
Deluxe Queen Room with 2 Queen Beds
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Food and drink

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.6 out of 10, Exceptional, (21)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
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.