Discover the Berkshires
Curated rental properties for every season.
Available Properties
Egremont, MA
Creamery Road
Monterey, MA
Laurel Banks Waterfront
Housatonic, MA
Conway House
Stockbridge, MA
Hadley House
Great Barrington, MA
Castle Townhouse
Egremont, MA
Stone Hill with Pool
New Marlborough, MA
Aberdeen
Monterey, MA
Lake Garfield Waterfront
Great Barrington, MA
Rosecliff Estate with Pool
Great Barrington, MA
Highland
EXPERIENCE THE BERKSHIRES
More Than Just a Stay
Curated homes backed by local expertise and personalized service.
Curated Homes for Every Stay
From cozy cottages to spacious estates, every home is carefully selected for location, comfort, and character.
The Rental-Ready Promise
Every home is professionally prepared for your arrival with clean linens, quality standards, and dependable support throughout your stay.
Your Local Berkshire Experts
Serving the region since 2005, we connect guests with homes that match the best of the Berkshires — from ski season to summer escapes.
Find Your Perfect Stay
Tailored to your lifestyle
Customer Reviews
4.96
Average trip rating, from 878 reviews
Happiest Winter We had the best winter of our lives thanks to this house. The winter just flew by because we were having so much fun. The house is great for our family -dog included! Within minutes from the house, we had access to skiing, hiking, excellent dining and shopping and so much more. Great Barrington is a lovely town! The stay was very easy for us as the house managers were extremely helpful with everything and anything we may need.
Excellent Perfect home in a perfect location. Extremely comfortable and functional space, well equipped, and close to so many things to do. Couldn't be better.
The property was perfect. Inside was impeccable with everything we needed with linens and fresh towels. For a good size group all the space and rooms were nice and we enjoyed the cozy couch and living room area. Wished the weather outside was warmer as we would have tried the hot tub. Beautiful quiet and private property too. Well stocked kitchen for our meal prep, etc. instructions for everything we needed was well outlined in the binder. We would definitely return in summer or fall. Highly recommend!
Thank you for a wonderful stay! Our family loved the time together in such a peaceful setting.
Cozy Home; Plenty of games provided as well kitchen amenities… Hot tub was a plus! <br/>I Suggest to Ask if the Grill is Ready to use!
Laurel banks ski house We had such a great time at this lovely house! It exceeded expectations in every way. House was adorable and super convenient to the mountain.
We had a great stay with our extended family for a ski trip at Butternut. Thank you!
Winter Ski Season Rental We loved our stay at Interlaken Cross. The location and views were magical. The entire team supporting the rental were so responsive and accommodating. We would absolutely stay here again!
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! ⛷️❄️
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.
Happiest Winter We had the best winter of our lives thanks to this house. The winter just flew by because we were having so much fun. The house is great for our family -dog included! Within minutes from the house, we had access to skiing, hiking, excellent dining and shopping and so much more. Great Barrington is a lovely town! The stay was very easy for us as the house managers were extremely helpful with everything and anything we may need.
Excellent Perfect home in a perfect location. Extremely comfortable and functional space, well equipped, and close to so many things to do. Couldn't be better.
The property was perfect. Inside was impeccable with everything we needed with linens and fresh towels. For a good size group all the space and rooms were nice and we enjoyed the cozy couch and living room area. Wished the weather outside was warmer as we would have tried the hot tub. Beautiful quiet and private property too. Well stocked kitchen for our meal prep, etc. instructions for everything we needed was well outlined in the binder. We would definitely return in summer or fall. Highly recommend!
Thank you for a wonderful stay! Our family loved the time together in such a peaceful setting.
Cozy Home; Plenty of games provided as well kitchen amenities… Hot tub was a plus! <br/>I Suggest to Ask if the Grill is Ready to use!
Laurel banks ski house We had such a great time at this lovely house! It exceeded expectations in every way. House was adorable and super convenient to the mountain.
We had a great stay with our extended family for a ski trip at Butternut. Thank you!
Winter Ski Season Rental We loved our stay at Interlaken Cross. The location and views were magical. The entire team supporting the rental were so responsive and accommodating. We would absolutely stay here again!
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! ⛷️❄️
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.
