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Vacation Homes in The Berkshires

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is ¥24,493
¥60,290 total
includes taxes & fees
Oct 28 - Oct 29
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Home in Great Barrington

9.8 out of 10, Exceptional, (24)
"Enjoyed our stay!!!"
The price is ¥22,679
¥38,673 total
includes taxes & fees
Nov 10 - Nov 11
Home in Great Barrington

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

9.6 out of 10, Exceptional, (8)
"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."
The price is ¥26,912
¥62,824 total
includes taxes & fees
Oct 27 - Oct 28
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is ¥24,342
¥71,758 total
includes taxes & fees
Oct 13 - Oct 14
Comfortable Berkshires retreat on mtn resort, SISO

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
The price is ¥29,784
¥68,396 total
includes taxes & fees
Nov 4 - Nov 5
Cheerful 3-bedroom cottage with woodstove

North Getaway Cottage

9.2 out of 10, Wonderful, (22)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is ¥34,018
¥72,281 total
includes taxes & fees
Oct 27 - Oct 28
North Getaway Cottage

Cozy. Clean. Free bagel shop.

10.0 out of 10, Exceptional, (10)
"The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!"
The price is ¥60,476
¥100,315 total
includes taxes & fees
Nov 4 - Nov 5
Cozy. Clean. Free bagel shop.

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

9.8 out of 10, Exceptional, (71)
"We had a wonderful stay, thank you! "
The price is ¥39,612
¥81,061 total
includes taxes & fees
Oct 13 - Oct 14
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

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 ¥43,089
¥78,529 total
includes taxes & fees
Nov 2 - Nov 3
Great Barrington Get Away

Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

10.0 out of 10, Exceptional, (1)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
The price is ¥34,018
¥47,962 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

Sun Filled Lenox Retreat - Minutes to Tanglewood!

9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
The price is ¥25,853
¥66,708 total
includes taxes & fees
Oct 13 - Oct 14
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Easy check in and communication was great. "
The price is ¥45,357
¥62,655 total
includes taxes & fees
Oct 13 - Oct 14
Bungalow in the Berkshires

Cozy. Clean. Free bagel shop. 3 Fireplaces.

The price is ¥60,476
¥100,315 total
includes taxes & fees
Nov 4 - Nov 5
Cozy. Clean. Free bagel shop. 3 Fireplaces.

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

2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is ¥40,685
¥73,818 total
includes taxes & fees
Oct 14 - Oct 15
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Spacious 5-bedroom house in charming Lee with WiFi

The price is ¥68,036
¥124,127 total
includes taxes & fees
Oct 21 - Oct 22
Spacious 5-bedroom house in charming Lee with WiFi

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

10.0 out of 10, Exceptional, (1)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
The price is ¥95,114
¥212,974 total
includes taxes & fees
Oct 13 - Oct 14
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (14)
"Amazing Inn. Cozy and everything we needed. "
The price is ¥83,003
¥158,355 total
includes taxes & fees
Nov 7 - Nov 8
Hancock Village Inn at Jiminy Peak

Peaceful Stay at Birds of a Feather Farm & Spa

9.8 out of 10, Exceptional, (27)
"Amazing… our stay was just what we needed. Everything you can think of was included at Peaceful Stay at Birds of a Feather Farm & Spa. The bed was super comfy, the towels were great, cannot say enough about this place. Highly recommend! "
The price is ¥14,287
¥36,662 total
includes taxes & fees
Oct 13 - Oct 14
Peaceful Stay at Birds of a Feather Farm & Spa

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (39)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
The price is ¥17,553
¥30,753 total
includes taxes & fees
Oct 19 - Oct 20
Lovely 2nd Floor Apartment

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
10.0 out of 10, Exceptional, (6)
"The property was great and the house was huge even for all 12 of us "
The price is ¥15,164
¥95,756 total
includes taxes & fees
Oct 14 - Oct 15
CT Gate House Goshen CT, Gate House Goshen CT
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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