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Vacation Homes in Canaan

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (257)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is AED 551
AED 837 total
includes taxes & fees
16 Sep - 17 Sep
Berkshire Village Carriage House - Super Private!!

All the comforts of home

9.0 out of 10, Wonderful, (24)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
The price is AED 390
AED 519 total
includes taxes & fees
3 Sep - 4 Sep
All the comforts of home

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is AED 988
AED 1,822 total
includes taxes & fees
11 Sep - 12 Sep
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is AED 612
AED 1,015 total
includes taxes & fees
3 Sep - 4 Sep
Home in Great Barrington

Upstate Lake house Retreat-a peaceful and relaxing feeling to recharge the soul

10.0 out of 10, Exceptional, (1)
"This sturdy, small house has everything you need to enjoy a get-away by a pretty lake. Lakeview always available through the large living-room windows and convenient & spacious dining area. 2 porches with seating are lit in evenings for a cozy feel. In addition, there is a large side/back yard with a fire pit, seating & ambiance lights. Other than not being handicap accessible, (steps to get in & steep steps with railings to the upstairs bedrooms), it is a really cute house! Host left fruit &...
The price is AED 714
AED 1,355 total
includes taxes & fees
3 Sep - 4 Sep
Upstate Lake house Retreat-a peaceful and relaxing feeling to recharge the soul

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (3)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
The price is AED 749
AED 1,735 total
includes taxes & fees
3 Sep - 4 Sep
NEW RENO Historic Creamery in Berkshires w/hot tub

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (1)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
The price is AED 837
AED 1,867 total
includes taxes & fees
3 Sep - 4 Sep
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is AED 591
AED 1,743 total
includes taxes & fees
3 Sep - 4 Sep
Comfortable Berkshires retreat on mtn resort, SISO

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time. "
The price is AED 871
AED 1,818 total
includes taxes & fees
9 Sep - 10 Sep
Cheerful 3-bedroom cottage with woodstove

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (2)
"Great location, very clean and well appointed with everyth"
The price is AED 1,377
AED 1,854 total
includes taxes & fees
3 Sep - 4 Sep
Bungalow in the Berkshires

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is AED 742
AED 1,654 total
includes taxes & fees
3 Sep - 4 Sep
Near Tanglewood: Historic Summer Retreat

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is AED 1,781
AED 2,958 total
includes taxes & fees
3 Sep - 4 Sep
The Lakeshore House

Treat yourself at the stunning June Farms Wellness Huts!

10.0 out of 10, Exceptional, (8)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
The price is AED 972
AED 1,711 total
includes taxes & fees
3 Sep - 4 Sep
Treat yourself at the stunning June Farms Wellness Huts!

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,847 total
includes taxes & fees
3 Sep - 4 Sep
Hancock Village Inn at Jiminy Peak

3-bedroom house in beautiful Berkshires, close to amenities!

The price is AED 738
AED 1,210 total
includes taxes & fees
10 Sep - 11 Sep
3-bedroom house in beautiful Berkshires, close to amenities!

Experience Timeless Elegance in The Edith Wharton Room!

The price is AED 762
AED 1,118 total
includes taxes & fees
4 Sep - 5 Sep
Experience Timeless Elegance in The Edith Wharton Room!

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
The price is AED 1,102
AED 1,953 total
includes taxes & fees
1 Oct - 2 Oct
Great Barrington Get Away

Cozy. Clean. Free bagel shop. 3 Fireplaces.

The price is AED 1,322
AED 2,215 total
includes taxes & fees
3 Sep - 4 Sep
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Spacious 5-bedroom house in charming Lee with WiFi

The price is AED 1,194
AED 2,462 total
includes taxes & fees
9 Sep - 10 Sep
Spacious 5-bedroom house in charming Lee with WiFi
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