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Check prices for these dates

Next weekend
31 Muh. - 2 Saf.
In two weeks
7 Saf. - 9 Saf.
In one month
21 Saf. - 23 Saf.
In two months
21 Rab. I - 23 Rab. I

Compare 255 Vacation Homes in East Canaan with updated reviews, rates, and availability.

Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (203)
"The house was great with plenty to do in the area. It was warm, comfortable, and just what we were looking for a quick weekend away. Would definitely return.Thanks,-Mike"
Peace and quiet on the lake
Spectacular views and close to Great Barrington.
Private kitchen

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.
Beautiful Berkshire Farm House on 160+ Acres
Exterior

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (36)
"This was our second group visit to the Berkshire Farm House, and we plan to go back again! That fact says it all. "
Beautiful Berkshire Farm House on 160+ Acres
Berkshires Lakefront Retreat
Sunsets on the lake

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (4)
"Amazing view!!!They thought of everything even things we didn’t think we wanted, right down to little things like motion sensing lights in the bathrooms. I’m a chef and cooked for my friends and I was surprised they had everything I needed. We are looking forward to coming back for another stay."
Berkshires Lakefront Retreat
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Living area

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

9.4 out of 10, Exceptional, (20)
"Well located and comfortable "
The price is SAR 634
SAR 1,291 total
includes taxes & fees
31 Jan - 1 Feb
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
The Goshen Glass Chalet

The Goshen Glass Chalet

9.4 out of 10, Exceptional, (29)
"Nice and cozy property. The host has been very responsive. "
The Goshen Glass Chalet
Hudson Valley and The Berkshires getaway
Kitchen and dining room

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (5)
"We loved our stay on Stone Ledge Rd in Hillsdale. We have stayed at Vrbo properties in Hillsdale two prior holiday weeks leading up to the New Year and this was by far the best set-up for us—gorgeous views through the wrap-around windows, easy and comfortable sleeping arrangements for the 6 of us, plenty of sofa space for reading, watching movies, just hanging out. Ben was very responsive when a mixture of drizzle and freezing temperatures made the driveway slippery and we were able to park in...
Hudson Valley and The Berkshires getaway
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Start Your Day Right - Enjoy Complimentary Fresh Bagels From Around the Corner!

BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

2.0 star property
8.8 out of 10, Excellent, (3)
"Property is lovely and very well maintained. We stayed for over 10 days and it was a perfect home away from home. Owners are very kind and accommodating — when I couldn’t find a hair dryer one was delivered to the house within a couple of hours. They also offered to relocate us if we were bothered by the nearby forest fire, which was not necessary. I hope we’ll have the opportunity to stay again."
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"Beautiful, well-stocked home with a lovely lake view. "
Quintessential 6-BR Berkshires Lodge
Stockbridge Home, Come Experience The Berkshires!

Stockbridge Home, Come Experience The Berkshires!

10.0 out of 10, Exceptional, (24)
"We enjoyed everything about this lovely house in the Berkshires--the latest appliances, thoughtful details (throws on all the beds and sofas), a great backyard. Would highly recommend! "
Stockbridge Home, Come Experience The Berkshires!
Peaceful, Post and Beam Loft, Sleeps 9

Peaceful, Post and Beam Loft, Sleeps 9

10.0 out of 10, Exceptional, (15)
"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."
Peaceful, Post and Beam Loft, Sleeps 9
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated
Exterior

Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

9.8 out of 10, Exceptional, (9)
"We loved our stay! Andrea responded to questions very quickly. The house was very clean and had everything we needed. We appreciated the treat that was left on the island. We were there only 2 nights and wish we stayed longer. We would definitely stay again. "
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated
Elegant 19th Century New England 2BR vacation rental at Garfield House
Exterior

Elegant 19th Century New England 2BR vacation rental at Garfield House

10.0 out of 10, Exceptional, (89)
"Superb location in town with charm galore . Perfect spot for our 3 day weekend in the Berkshire’s An excellent enjoyable stay !"
Elegant 19th Century New England 2BR vacation rental at Garfield House
A Grand property in Historic Stockbridge
The Taggart House

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (94)
"This was our fourth stay at this magnificent property and we continue to be amazed by its beauty and grandeur. Our host have provided us with everything to make our experience perfect. The house is well equipped and well-maintained. I would highly recommend this rental for a first-class experience. Thank you to George and Caitlin for their hospitality and kindness.."
A Grand property in Historic Stockbridge
LAKE FRONT LAKE BUEL Monterey 10 M GREAT BARRINGTON HOUSE VIEWS PRIVATE DOCK
LAKE VIEWS

LAKE FRONT LAKE BUEL Monterey 10 M GREAT BARRINGTON HOUSE VIEWS PRIVATE DOCK

10.0 out of 10, Exceptional, (39)
"house is clean, well maintained, and well stocked. Owners very responsive."
LAKE FRONT LAKE BUEL Monterey 10 M GREAT BARRINGTON HOUSE VIEWS PRIVATE DOCK
Large Barn styled vacation home that fits groups with space to spare.
Property grounds

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

9.8 out of 10, Exceptional, (57)
"Everything was ideal for our Thanksgiving get together. Setting and views were perfect, made even more so with a timely blanket of fresh snow. An amazing amount of cooking provisions allowed us to cook as if we were in our own kitchen. Lots of options for keeping a large group entertained, and sleeping accomodations that pleased everyone. Host was very helpful with check-in communications and gracious with check in and out times without other bookings adjacent to ours. All in all a very special...
Large Barn styled vacation home that fits groups with space to spare.
Minutes from downtown Great Barrington, Convenient location
Exterior

Minutes from downtown Great Barrington, Convenient location

10.0 out of 10, Exceptional, (44)
"House was comfortable and close to Butternut, catamount, and town. "
Minutes from downtown Great Barrington, Convenient location
Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington

Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.

10.0 out of 10, Exceptional, (20)
"We were a group of 4 long time girlfriends on a Girls' Weekend. This house was perfect for us. The house is set fairly far back from the road which gives you an abundance of privacy. There are 3 bedrooms (king, king, and 2 full beds). If you don't mind sharing a room with one of your besties, then this completely updated home is for you! We selected the home for the hot tub and firepit. We used the hot tub both nights of our weekend stay! We loved the lights in the trees...was so relaxing...
Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.
5 Minutes from Catamount Ski Area
Dining

5 Minutes from Catamount Ski Area

9.0 out of 10, Wonderful, (21)
"Cozy spot after skiing. "
5 Minutes from Catamount Ski Area
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Summer in The Berkshires

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10.0 out of 10, Exceptional, (19)
"Amazing and lovely"
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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Other property types in East Canaan

Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (203)
"The house was great with plenty to do in the area. It was warm, comfortable, and just what we were looking for a quick weekend away. Would definitely return.Thanks,-Mike"
Peace and quiet on the lake
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Lake-we provide kayaks and a canoe!

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (210)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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.