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Holiday Homes in The Berkshires
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Our top choices for The Berkshires holiday homes
Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (26)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
Cameron M.
The price is NZ$441
includes taxes & fees
5 Jan - 6 Jan 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!Sherwood Forest
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 NZ$644
includes taxes & fees
4 Jan - 5 Jan 2026
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, DineSherwood Forest
9.6 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 NZ$672
includes taxes & fees
5 Jan - 6 Jan 2026
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
Tristan e.
The price is NZ$628
includes taxes & fees
4 Jan - 5 Jan 2026
3-bedroom house in beautiful Berkshires, close to amenities!
3-bedroom house in beautiful Berkshires, close to amenities!Pittsfield
The price is NZ$548
includes taxes & fees
12 Jan - 13 Jan 2026
Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
Kelly R.
The price is NZ$866
includes taxes & fees
5 Jan - 6 Jan 2026
Family Ski Getaway in the Berkshires
Family Ski Getaway in the BerkshiresGreat Barrington
9.4 out of 10, Exceptional, (6)
"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)...
Kathy C.
The price is NZ$510
includes taxes & fees
3 Jan - 4 Jan 2026
Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISOHancock
9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
Javier
The price is NZ$1,255
includes taxes & fees
3 Jan - 4 Jan 2026
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.
Top The Berkshires Hotel Reviews
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The Berkshires Holiday Homes information
Number of reviews | 278 |
|---|---|
Accommodation | 324 Holiday Homes |
Lowest Price | NZ$345 |
Highest Price | NZ$3,011 |
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