Chalet holiday rentals in Massachusetts

This was our 2nd stay at this property. If you love the Berkshires and all the activities available, this house and property are perfect. It is very well maintained and the great room is perfect for our large family. Nothing like the hot tub and sitting around a fire after a busy day of hiking and Tanglewood. Wendy is an excellent host, never a problem.

This is my favorite rental. It is so cozy and open at the same time. There is plenty of space for everyone with two twin beds, a king bed in the loft, a fold out sofa and a queen bedroom downstairs for my daughter. The woods are beautiful and the house is in a quiet location. At the same time, it is not too far from the Allendale shopping area in Pittsfield, small stores in Hinsdale, as well as Williamsburg and Northampton. The house is very warm even in the winter, comes with everything you need to cook, and has laundry. The bedrooms are comfortable and bathrooms are nice. The TV and WIFI streaming work great. There is an extra long table which we use for games and a deck overlooking the backyard. Overall, it is a great place to stay for families.

Absolutely amazing stay! I have never stayed with such hospitable and genuinely nice hosts. In addition their home was filled with interesting gadgets and beautiful aesthetic, they’ve inspired to replace every toilet in my house! I hope I have the pleasure of staying here again! Thank you Jennifer and Evan!

The chalet was perfect for our relaxing 5 day vacation. We enjoyed swimming off the dock and taking the kayaks out on the lake. The space is wonderful and the view is amazing! We found it hard to get motivated to go out to dinner and lunch because we didn't want to miss one second of the wonderful view!

Absolutely beautiful and well maintained cabin. Professional kitchen, with all the things and every sort of glass you’d need for entertaining. Fireplace was so perfect on a cold night, game room downstairs was perfect for us - half of the group cozied up and watched a movie and the others played a friendly round or three of pool. Games galore so you’re never bored; it’s clear that anyone who stays here has a blast. Jacuzzi for a cold winter night was awesome and though the neighbors aren’t far you feel like you’re out in the middle of nowhere. And, you’re just about 15 mins from Great Barrington with all the shops and quaint Main Street. Perfect weekend getaway for our group.

We had a peaceful 5- night getaway at Katherine’s. The bed was one of the most comfortable I’ve ever slept on! The weather ranged from the 16 degrees on our first night to nearly 65 degrees on our last day - we were comfortable through all of it. And the views! The views from the octagon house are stunning, and instantly relaxing. The home is fully equipped with anything anyone could need. Chris at the Grouse House made us feel super welcome on our first night in Otis and we had great breakfasts at Paige’s Place right down the road (3 days in a row! Shout out to Eric!). We also found some other great places like Antimony Brewing in Lennox, and Agave’s in Great Barrington - both within a 30 minute drive. Thanks again for sharing your home!

Always so great. Thanks so much. A wonderful house and a wonderful host.

This was our 2nd stay at this property. If you love the Berkshires and all the activities available, this house and property are perfect. It is very well maintained and the great room is perfect for our large family. Nothing like the hot tub and sitting around a fire after a busy day of hiking and Tanglewood. Wendy is an excellent host, never a problem.

Clemence's place is gorgeous and comfortable! Perfect stay for our group of friends catching up for the weekend. Super clean, the kitchen is extremely well stocked - much better than shows in the photos or is listed in the description. Private spot with plenty of space. Had a lovely walk in a nearby state park, too.

Great stay slopeside at Berkshire East. We had a wonderful week and the house was perfect. We had some trouble with the weather (and power) that was out of host's hands but they went above and beyond to stay in touch and help get through it. Great spot for family skiing, or group trip mountain biking, rafting, etc. Thanks!

Absolutely beautiful and well maintained cabin. Professional kitchen, with all the things and every sort of glass you’d need for entertaining. Fireplace was so perfect on a cold night, game room downstairs was perfect for us - half of the group cozied up and watched a movie and the others played a friendly round or three of pool. Games galore so you’re never bored; it’s clear that anyone who stays here has a blast. Jacuzzi for a cold winter night was awesome and though the neighbors aren’t far you feel like you’re out in the middle of nowhere. And, you’re just about 15 mins from Great Barrington with all the shops and quaint Main Street. Perfect weekend getaway for our group.