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Compare 311 Vacation Homes in Canaan with updated reviews, rates, and availability.

Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is ¥34,092
¥72,467 total
includes taxes & fees
Oct 6 - Oct 7
Cheerful 3-bedroom cottage with woodstove
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (141)
"Great place and views. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Charming 1870 cape cottage in Litchfield
10.0 out of 10, Exceptional, (31)
"Beautiful house"
Charming 1870 cape cottage in Litchfield
Peace and quiet on the lake
9.6 out of 10, Exceptional, (190)
"Loved it!"
Peace and quiet on the lake
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (19)
"The house is lovely and so perfectly located. The two bedrooms were sufficiently apart and next to their own bathrooms so both couples had privacy.the screened in porch was perfect to hang out and play cards at night and my dog absolutely loved the back yard. The location is superb, conviently located central to Stockbridge, ,lenox and Great Barrington. Fifteen minutes to Tanglewood and the Norman Rockwell museums. There are so many hiking trails with fabulous mountain views nearby."
Stockbridge Home, Come Experience The Berkshires!
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.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
10.0 out of 10, Exceptional, (36)
"We had a wonderful stay as a group of 6 adults and 2 children. The house was very comfortable and clean. We appreciated the well stocked kitchen and excellent set up for kids. The location felt private but was still only a few minutes drive from Great Barrington. Thank you for a great visit! "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Garfield Townhouse in the Berkshires on Main St
10.0 out of 10, Exceptional, (8)
"We very much enjoyed our stay at Garfield House and hope to be back someday. Our host Jeff was responsive and available for anything we needed. The unit was clean and set up just as shown. Highly recommend to anyone interested in staying in a great Berkshire town."
Garfield Townhouse in the Berkshires on Main St
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"I don’t want to publish review, but I really think the owners should let people know that two of thee bedrooms are in the basement and one has no windows. Also a big issue is the firing range next door. Gunshots every day and a poor dead bird on deck. Afraid to go outside!!!"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
10.0 out of 10, Exceptional, (16)
"House was fantastic—clean, comfortable, and in a great location. Alyssa was always available by text and cheerfully helped us deal promptly with a couple of minor hiccups while we were there. We have already rebooked for next year!"
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
Mountain View Getaway
10.0 out of 10, Exceptional, (41)
"This is our second year staying with at Karen and Larry’s property and it did not disappoint. They are incredible hosts and their home is conveniently located near the Lime Rock Track (less than 3 miles). It’s a beautiful and peaceful setting and extremely comfortable home. We highly recommend."
Mountain View Getaway
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (24)
"We stayed at the Meadow House over Labor Day weekend. Lars was super accommodating to us and made sure we were taken care of. Really quick responses from him and he’s even working with us to return something one of the friends I was with left behind. Definitely recommend this house if you’re looking to escape the city or go hiking near by."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Quintessential 6-BR Berkshires Lodge
9.8 out of 10, Exceptional, (7)
"Nice. Quiet. The new pool is very nice."
Quintessential 6-BR Berkshires Lodge
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (82)
"We had 15 people stay for three nights for a family reunion - 9 adults and 6 kids. The house worked well, as all had reasonably private spaces. The countryside is beautiful. Visits to a lake for swimming and several local waterfalls worked well for all."
Antique Farmhouse Totally Restored
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.6 out of 10, Exceptional, (13)
"Me and my husband and my sister and her husband came to the Hudson Valley to place a bench in his hometown in his memory. We thoroughly enjoyed our time at this property. It was just exactly what we needed-quiet and relaxing!"
The price is ¥22,872
¥47,836 total
includes taxes & fees
Sep 24 - Sep 25
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
9.0 out of 10, Wonderful, (4)
"We loved staying here! Great location!"
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (23)
"Stayed for labor day with family from out of state. Plenty of room for 4 adults and 4 kids, Could have easily fit more. Had a great time on the dock and having fires in the back yard. "
Family House On Highland Lake with Dock
Remodeled Lakefront retreat Come See the Fall Foliage and roll into Ski Season!!
9.4 out of 10, Exceptional, (3)
"Very peaceful! Enjoyed spending time at the lake. Nicely remolded. Outlet in masterbath was not useable. Our 1st day there someone came walking on the deck. Turned out to be an exterminator. Wasp problem. We helped him look and didn't see anything at the time, although later, they were back with a vengance. Both myself and daughter were stung at different times. Im sure the exterminator will return, but we had to use inconvient doors to enter and exit and my daughter was scared to...
Remodeled Lakefront retreat Come See the Fall Foliage and roll into Ski Season!!
Waterview Home in the Berkshires: Near Hiking
9.4 out of 10, Exceptional, (19)
"My partner and I had a lovely stay for our visit to the Berkshires. The house was the perfect place to relax and unwind after a day exploring the area. The location is ideal with plenty of shops near by for essentials but still felt secluded. We hope to come back soon!"
Waterview Home in the Berkshires: Near Hiking
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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 & renovated, comfort, peaceful nature.
9.8 out of 10, Exceptional, (8)
"We LOVED our stay at this property! It was IMMACULATE!! It’s spacious, comfortable and homey. Our hostess, Andrea, was extremely responsive to any questions we had. We loved walking “down the road” from the property to visit the farms and the winery! Perfect for a family with adult members ( the kitchen set up is AMAZING!! A cook’s delight!) and children as well! The kids have their own playground! Andrea deserves a 10- she’s put a LOT of love and attention into her house."
Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (205)
"My stay was shorter than I had planned but the few days I was here was so relaxing. First of all, the bed is so comfortable, I slept like a baby. Very quiet area. Nice to walk around with my dogs and explore. The cottage was nicely outfitted with any needs you might have. Beautiful time of year to stay here! I cannot wait to go back. I also want to say I appreciate that they allowed my two dogs. My dogs are very well behaved, and I travel with them quite often. Not all places allow this, so I...
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
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.