Discover the Berkshires
Curated rental properties for every season.
Available Properties

Great Barrington, MA
Castle Townhouse
3 bedrooms•3 beds•2 baths

Great Barrington, MA
Laurel Cottage
3 bedrooms•3 beds•2 baths

Hillsdale, NY
Breezy Hill
4 bedrooms•4 beds•2 baths

Great Barrington, MA
White Birch
4 bedrooms•4 beds•3 baths

Monterey, MA
Lake Garfield Waterfront
3 bedrooms•3 beds•4 baths

Sheffield, MA
Dixon Cottage
3 bedrooms•3 beds•2 baths

Egremont, MA
Lakeside Cottage
3 bedrooms•3 beds•1 bath

Stockbridge, MA
Hadley House
4 bedrooms•4 beds•2 baths

Monterey, MA
Sweetwater
4 bedrooms•4 beds•2 baths

Sheffield, MA
Riverside
4 bedrooms•4 beds•3 baths
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More Than Just a Stay
Curated homes backed by local expertise and personalized service.
Find Your Perfect Stay
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Customer Reviews
4.9
Average trip rating, from 395 reviews
5 / 5
We had such a wonderful stay at this beautiful home in the Berkshires! It was the perfect spot for our families while we were up skiing at Butternut. The house was incredibly cozy and inviting—it truly felt like a home that is loved and well cared for by a great family.<br/>Everything was spotless when we arrived, and there was plenty of space for all of us and our kids to spread out and relax after long days on the mountain. It had that warm, comfortable feeling that made it easy to settle right in.<br/>We made some great memories here and had an absolute blast. We’re already looking forward to coming back and renting this special home again next year! ⛷️❄️
KathrynStayed in March 2026
5 / 5
Fantastic place for a couple of weekends to ski at butternut. Our kids loved the house, it was as close as you can get to the slopes - truly great overall experience. Would go again, for longer. Very responsive host.
LucianStayed in February 2026
5 / 5
Great house! Tons of space. We had a blast
EmilyStayed in February 2026
5 / 5
We had such a wonderful stay here! The house is warm and full of character. So many great spaces for groups to relax and socialize. We were 4 families and all loved it! We highly recommend it and hope to return in the future.
CaitlinStayed in January 2026
5 / 5
We had a lovely stay with two other families ! Plenty of room for all adults and kids. Extremely comfortable, clean and well decorated home in a great location !
LindseyStayed in January 2026
5 / 5
Our group of three families had a great stay! We loved the multiple living spaces. Kids took over the media room upstairs and we sat by the fire in the kitchen, played games at the dining room table, and hung out in the living room. Perfect Berkshires location - close to town of Great Barrington and Butternut mountain for a ski day.
ErinStayed in January 2026
5 / 5
It was observed that during the stay, the removal of the trash was suggested, but when we arrived, the trash cans were full. Therefore, we left the trash removed from inside the house and bagged next to the trash cans.
DesirêStayed in January 2026
5 / 5
Me and my family had a wonderful stay! Strongly recommended!
TedStayed in January 2026
5 / 5
Amazing place, feel like paradise lost in the Forrest.
Marie-NouraStayed in January 2026
5 / 5
Spacious and beautiful cabin space would come back again!!
KevinStayed in January 2026
5 / 5
We had such a wonderful stay at this beautiful home in the Berkshires! It was the perfect spot for our families while we were up skiing at Butternut. The house was incredibly cozy and inviting—it truly felt like a home that is loved and well cared for by a great family.<br/>Everything was spotless when we arrived, and there was plenty of space for all of us and our kids to spread out and relax after long days on the mountain. It had that warm, comfortable feeling that made it easy to settle right in.<br/>We made some great memories here and had an absolute blast. We’re already looking forward to coming back and renting this special home again next year! ⛷️❄️
KathrynStayed in March 2026
5 / 5
Fantastic place for a couple of weekends to ski at butternut. Our kids loved the house, it was as close as you can get to the slopes - truly great overall experience. Would go again, for longer. Very responsive host.
LucianStayed in February 2026
5 / 5
Great house! Tons of space. We had a blast
EmilyStayed in February 2026
5 / 5
We had such a wonderful stay here! The house is warm and full of character. So many great spaces for groups to relax and socialize. We were 4 families and all loved it! We highly recommend it and hope to return in the future.
CaitlinStayed in January 2026
5 / 5
We had a lovely stay with two other families ! Plenty of room for all adults and kids. Extremely comfortable, clean and well decorated home in a great location !
LindseyStayed in January 2026
5 / 5
Our group of three families had a great stay! We loved the multiple living spaces. Kids took over the media room upstairs and we sat by the fire in the kitchen, played games at the dining room table, and hung out in the living room. Perfect Berkshires location - close to town of Great Barrington and Butternut mountain for a ski day.
ErinStayed in January 2026
5 / 5
It was observed that during the stay, the removal of the trash was suggested, but when we arrived, the trash cans were full. Therefore, we left the trash removed from inside the house and bagged next to the trash cans.
DesirêStayed in January 2026
5 / 5
Me and my family had a wonderful stay! Strongly recommended!
TedStayed in January 2026
5 / 5
Amazing place, feel like paradise lost in the Forrest.
Marie-NouraStayed in January 2026
5 / 5
Spacious and beautiful cabin space would come back again!!
KevinStayed in January 2026












