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Compare 336 Vacation Homes in Canaan with updated reviews, rates, and availability.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (210)
"This was a cozy tucked away location that seemed far away from everything which was exactly what we wanted. The host was extremely communicative before and during the stay. The house had fresh linens and towels as well as basic cleaning supplies. It was cozy for a wintery weekend in. We enjoyed snowshoeing on the frozen lake! Pet-friendly was a huge plus! "
Peace and quiet on the lake

Remodeled Lakefront retreat!! Come join us for Ski Season!!

9.6 out of 10, Exceptional, (5)
"We skied, we played in the snow and overall just relaxed at this perfect home!"
Remodeled Lakefront retreat!! Come join us for Ski Season!!

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, (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

Home in Great Barrington

9.6 out of 10, Exceptional, (19)
"Our family had a wonderful experience and stay. "
The price is AED 790
AED 1,210 total
includes taxes & fees
19 Mar - 20 Mar
Home in Great Barrington

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (6)
"Outfitted with everything a guest could want or need, from a fully equipped kitchen, linens, and cozy afghans to marshmallows for the hot chocolate. Spacious house with lots of places to gather or spread out. Beautiful setting—snow covered frozen lake. We would love to return in warm weather to make use of the lakefront. Very responsive and considerate host. "
Berkshires Lakefront Retreat

Lee Manor Berkshire House for Lasting Memories. 5 Bedrooms. 5 Full Bathrooms.

10.0 out of 10, Exceptional, (9)
"Our family of six stayed at Lee Manor during the Christmas holidays. The house was a lovely older home with modern amenities. It was very well stocked with all the needs of home. The house was spacious and the beds were very comfortable. We enjoyed the back sitting area with the stove heater for watching movies, playing games in the front room, and gathering in the kitchen for snacking. We had great communication with the owners and the Check-in and Check-out process was flawless. It was a...
Lee Manor Berkshire House for Lasting Memories. 5 Bedrooms. 5 Full Bathrooms.

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (46)
"This property was lovely. As a former resident in CT, I appreciate the New England charm. The house was pristine. Unfortunately I was in for a memorial and during a snow storm. Jeffrey and his family were so accommodating and so kind to us. I highly recommend this home. I would not hesitate to stay there again. "
Charming 1870 cape cottage in Litchfield

Mountain View Getaway

10.0 out of 10, Exceptional, (49)
"Such a magical place…always enjoy our stay. The home is so comfy - the hosts are amazing. "
Mountain View Getaway

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!"
The price is AED 621
AED 1,253 total
includes taxes & fees
12 Mar - 13 Mar
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater | Sunny Pond

10.0 out of 10, Exceptional, (139)
"We had a wonderful trip, the kitchen is fully stocked with tons of kitchen tools, 2 slow cookers, etc! Cooking basics were available, soaps, dishwasher pods etc! The rooms were great! The playroom was amazing for all the kids! We had a wonderful time and will be back! "
Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater | Sunny Pond

Linden by AvantStay | Countryside Berkshire Escape

9.6 out of 10, Exceptional, (9)
"Our family had a wonderful time staying at Linden House. It was comfortable for the 6 adults and 4 young children. We loved the sophisticated charm of the house with its beautiful artwork and furnishings. It has quality appliances and a fully equipped kitchen. We plan to return next year."
Linden by AvantStay | Countryside Berkshire Escape

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

Monterey Home w/ Hot Tub, Pool & Game Room!

9.0 out of 10, Wonderful, (2)
"Beautiful property. Lovely grounds. Clean and so much fun for the little ones. Communication and service were excellent. "
Monterey Home w/ Hot Tub, Pool & Game Room!

Beautiful Berkshires Colonial on 7 acres

10.0 out of 10, Exceptional, (5)
"Our family of 4 really enjoyed staying in this cozy, comfortable and beautifully-decorated farmhouse. Communication with the owners was easy and they had lots of great tips for enjoying the area, and the house had all of the essentials needed for a great weekend away. We’d intended to ski at nearby Catamount or Butternut but didn't manage to book lessons in time (lesson learned: book early for holiday weekends!), but Jiminy Peak was a great alternative an easy day trip further north. We’d...
Beautiful Berkshires Colonial on 7 acres

Lakeside 3-BR Berkshires Residence

10.0 out of 10, Exceptional, (3)
"Property very nice - loved the fireplace which was necessary due to cold temps and very windy conditions. Cooked dinner each night and kitchen very well equipped. Beds comfortable. Enjoyed hot tub once but then became too windy to use. "
Lakeside 3-BR Berkshires Residence

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (20)
"Couldn't ask for anything better. A big living room to hang out together, open-plan with the kitchen. Perfectly comfortable!"
Secluded Family Home in Serene Stockbridge Woods

Charming Columbia County Farm House

9.4 out of 10, Exceptional, (23)
"Our family had a wonderful time staying at this home. We played many games at the table and watched the fire burn in the stove. It was a cozy place with reading areas and the capability to get off screen time for the kids. "
Charming Columbia County Farm House

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!

Lakeside Peninsula Escape

Lakeside Peninsula Escape
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

Peace and quiet on the lake

9.6 out of 10, Exceptional, (210)
"This was a cozy tucked away location that seemed far away from everything which was exactly what we wanted. The host was extremely communicative before and during the stay. The house had fresh linens and towels as well as basic cleaning supplies. It was cozy for a wintery weekend in. We enjoyed snowshoeing on the frozen lake! Pet-friendly was a huge plus! "
Peace and quiet on the lake

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (14)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

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
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.