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Compare 398 Vacation Homes in Canaan with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (149)
"The location is beautiful and there are lots of places to visit in the area. The house is nice; great view of Otis Reservoir. It took us a while to figure out the multiple thermostats, but it was a good Christmas house. The owner was nice enough to allow us to have a Christmas tree, and had someone make an extra trash pick up for us after Christmas.The one thing we were disappointed in was the cleanliness. Shower curtains were moldy, some of the dishes weren't very clean, expired condiments...
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

Mountain View Getaway

10.0 out of 10, Exceptional, (50)
"From the moment we walked into this house , we were wowed. The incredible picturesque views that streamed in through all the wi dies in the house made us feel like we were enveloped by nature. We were able to enjoy sunsets and sunrises from the panoramic windows and the house itself was exceptionally clean, had quality appliances and everything g we would need to prepare meals. Karen and Larry, our hoses, were extremely responsive and accommodating. There were beautiful roses, snacks and...
Mountain View Getaway

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

9.6 out of 10, Exceptional, (213)
"This property was in an incredible location with a nice cozy feel. It was perfect for my family of 6. I highly recommend this place!"
Peace and quiet on the lake

Lakeside Retreat Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"It's a really lovely home on a beautiful property, with all the amenities we could have possibly needed, and also perfectly peaceful. The host was so welcoming and responsive, which made it that much nicer, too. My only regret is that we couldn't stay longer, and I would definitely want to stay there again. "
Lakeside Retreat Just You, The Lake & The View!

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

9.6 out of 10, Exceptional, (25)
"Our family of 4 stayed here while skiing at Catamount - great proximity, exactly as pictured, clean, and perfect size. Host was responsive - would stay here again!"
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

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

10.0 out of 10, Exceptional, (35)
"The property was centrally located for skiing, and was a comfortable stay."
The price is SAR 702
SAR 1,644 total
includes taxes & fees
7 May - 8 May
Cheerful 3-bedroom cottage with woodstove

Perfect Nature Retreat 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 Retreat In Great Barrington

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

9.4 out of 10, Exceptional, (8)
"The location was great and just a short walk to downtown. We thought the pictures on the site were a bit misleading. The house looked a little more open than it actually was, especially in the kitchen. The outside fire pit area was a little run down. A chair was broken and the string lights were down on the ground, water filled and no outlet to plug into. Plenty of bed space for everyone to sleep and beds were comfortable. Plenty of extra sheets and towels and the kitchen was well equipped. We...
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Private Estate, Heated Yearround Outdoor Pool

9.8 out of 10, Exceptional, (17)
"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."
Private Estate, Heated Yearround Outdoor Pool

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (33)
"Great place. Really enjoyed staying there"
The Goshen Glass Chalet

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

10.0 out of 10, Exceptional, (45)
"We had an amazing long ski weekend at the Great Escape Ski Cottage. The listing is very accurate. Great communication with Shay. The house was immaculate upon arrival. The layout of the house was perfect for our family (6 adults and 4 children aged 4-9). One beautiful Master Bedroom on the first floor. Two of the other equally beautiful bedrooms are on the second floor. The linens were hotel quality! The "Kid's Quarters" was located off of the kitchen/laundry room. A playroom with multiple games...
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

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.

Home in Great Barrington

9.6 out of 10, Exceptional, (19)
"Our family had a wonderful experience and stay. "
The price is SAR 826
SAR 1,262 total
includes taxes & fees
27 Apr - 28 Apr
Home in Great Barrington

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

10.0 out of 10, Exceptional, (53)
"This property is a perfect place to gather family or friends. Its beautifully appointed bedrooms and study gave individual family members space for privacy and one-on-one conversations, and its three large and elegant spaces--living room, dining room, and kitchen/family room--allowed all of us to gather for games, conversations, and meals. Because we stayed Christmas week we couldn't take advantage of the property's gorgeous outdoor spaces, but Lauren provided us with a decorated Christmas tree...
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

10.0 out of 10, Exceptional, (120)
"Really enjoyed our stay. Open-plan downstairs with spacious kitchen, two dining areas, amazing sectional that fit all of us for movie night. Great fireplace where we enjoyed a couple fires."
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Lakeside 5-BR Home in Idyllic Berkshires

10.0 out of 10, Exceptional, (1)
Lakeside 5-BR Home in Idyllic Berkshires

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

10.0 out of 10, Exceptional, (16)
"The perfect home for a weekend away. Extremely clean and welcoming. The host was so communicative and kind. 10/10 would stay here again."
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.
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 Canaan

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 Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (61)
"3 day holiday getaway, my husband and our 2 pups. A hike in nearby trails in the woods, enjoyed Lee downtown eateries and shops. Beautiful winter wonderland in the Berkshires. The guest rental was perfect!!! Warm, spacious, comfortable, perfect location. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (18)
"A great winter getaway in the Berkshires. We loved the location of this very nice spot in Great Barrington. Had some great dinners we could walk to and we were able to do amazing hikes during the day and visit other spots around GB as well. Would definitely recommend! House is clean and has a nice vibe and beds comfortable. Nice shower too!"
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.