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Our top choices for The Berkshires vacation homes
Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
Fred W.
$230 nightly
The price is $257
Jan 6 - Jan 7, 2026
Total with taxes and fees
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
Tristan e.
$316 nightly
The price is $339
Dec 23 - Dec 24
Total with taxes and fees
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.
$335 nightly
The price is $374
Dec 22 - Dec 23
Total with taxes and fees
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.
$346 nightly
The price is $387
Dec 22 - Dec 23
Total with taxes and fees
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside ConHancock
9.8 out of 10, Exceptional, (72)
"We had a wonderful stay, thank you! "
Gary L.
$592 nightly
The price is $661
Dec 23 - Dec 24
Total with taxes and fees
3-bedroom house in beautiful Berkshires, close to amenities!
3-bedroom house in beautiful Berkshires, close to amenities!Pittsfield
$281 nightly
The price is $314
Jan 12 - Jan 13, 2026
Total with taxes and fees
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.
$450 nightly
The price is $503
Jan 5 - Jan 6, 2026
Total with taxes and fees
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
$715 nightly
The price is $725
Dec 23 - Dec 24
Total with taxes and fees
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
Vacation Village in the Berkshires
10/10 Excellent
Find out more about The Berkshires
The Berkshires Vacation Homes information
Number of reviews | 338 |
|---|---|
Accommodation | 327 Vacation Homes |
Lowest Price | $201 |
Highest Price | $1,773 |
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