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Our top choices for Canaan vacation homes
Vacation Home in Goshen
CT Gate House Goshen CT, Gate House Goshen CT9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
Ryan L.
The price is AED 347
AED 2,309 total
includes taxes & fees
14 Dec - 15 Dec
Vacation Home in Sherwood Forest
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is AED 535
AED 1,386 total
includes taxes & fees
16 Dec - 17 Dec
Vacation Home in Great Barrington
Home in Great Barrington9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
Fred W.
The price is AED 573
AED 960 total
includes taxes & fees
6 Jan - 7 January 2026
Vacation Home in Sherwood Forest
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
James D.
The price is AED 588
AED 1,441 total
includes taxes & fees
16 Dec - 17 Dec
Vacation Home in Sheffield
Cheerful 3-bedroom cottage with woodstove10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
Kelly R.
The price is AED 724
AED 1,666 total
includes taxes & fees
15 Dec - 16 Dec
Vacation Home in Hillsdale
Perfect House In Hillsdale, Brings Friends & Fam8.4 out of 10, Very Good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
Stefanie K.
The price is AED 683
AED 1,971 total
includes taxes & fees
11 Dec - 12 Dec
Vacation Home in Housatonic
Sweet Cozy Victorian in Housatonic. Close to everything.10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
Cheryl F.
The price is AED 496
AED 890 total
includes taxes & fees
15 Dec - 16 Dec
Vacation Home in Great Barrington
Pet Friendly Riverfront Home in Great Barrington9.4 out of 10, Exceptional, (6)
The price is AED 744
AED 1,093 total
includes taxes & fees
15 Dec - 16 Dec
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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Top Canaan Hotel Reviews
Holiday Inn Express Hotel & Suites Great Barrington by IHG
10/10 Excellent
