Chalet vacation rentals in The Berkshires

Had an amazing time her with my friends. Very clean place and super nice cabin in the woods. Make sure you have a 4wd drive car in the winter to get up the driveway.

This was our second year staying here with friends, and we had such a lovely time. There's plenty to do inside the house itself even on a dreary day, with curiosities and art abound, instruments, games, fireplace, etc, a great kitchen for group meals, and spacious and comfortable rooms otherwise. Olia is very kind and responsive, with plenty tips for the local area. We'd recommend for groups or families in an instant. Nothing like relaxing in the hot tub while looking out at the mountain vista with rain pattering on the porch roof above - pure bliss.

Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!

Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!

Had a lovely time! It’s a beautiful house and Juris sent very clear and helpful instructions before check in. Would stay again.

Such a great and cozy stay! Minutes from town center and Windham, so easy to check in / check out. Very happy we stayed here!

Cozy Silo Home is a perfect description of Olga's home! The silo is really unusual, with lots of windows/lighting and is comfortable and nicely decorated. It's a short drive from Woodstock, which is a fantastic area with lots of shopping, restaurants, etc. It's also very close to great hiking and other outdoor activities. At the house, we spent most of our time outside on the large balcony/patio and cooking meals on the outdoor grill. We booked last-minute and Olga was very responsive, answered all our questions and made things very easy for us. We live in NYC and a weekend in/around Woodstock is a great way to recharge and reconnect with nature. We definitely recommend Olga's silo home for a weekend or longer!! Note: stairs are required to enter into the home and to get to the bedrooms/bathrooms, so don't bring anything too bulky or heavy.

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.

This is a truly beautiful home and property and we had a wonderful few days enjoying everything it had to offer! The kids between our two families had endless fun with the arcade, hot tub, exploring the property and creek, and the slumber party they got to have in the upper bedroom. As for the adults, we got to unwind and enjoy, as Stefanie has thought of everything as a host and made it a breeze to check in and relax. The couple hiccups or questions we had at the start were quickly answered and resolved through messages and all instructions for check out were easy and straightforward. Would love to book this home during ski season in the future as the views of and proximity to the mountain are amazing!

An awesome place for a ski getaway! The house is beautiful, and just down the road from the mountain. Would highly recommend!

Lovely stay with family and friends. The host went out of his way to ensure our arrival was smooth, even with a very icy driveway and up to two inches of snow falling. The space is beautiful, secluded and serene. But also close to restaurants in Mt. Tremper and good hikes.

We had so much fun at Eric’s. The kids frolicked in the beautiful surroundings, and loved the treehouse. The house had everything we needed and tons of space for our party of 7.

A beautiful spot perched amongst the trees and snowy woods. Cosy couches and fireplaces, a magical hot tub and generous touches, like extra wood, coffee and shampoo. I took my boys skiing nearby and we all loved every minute. Wouldn't hesitate to stay again

The property was spacious, clean, and well-equipped to accommodate our large group comfortably. Perfect for relaxing after a day on the slopes. The location was ideal, just a couple minutes drive from the ski resort. Bobby, the host, was incredibly responsive and helpful!. We couldn't have asked for a better place for our ski weekend and would highly recommend it to anyone looking for a great group getaway!

My wife and I stayed at Ron’s place for five nights for a winter getaway. We had a great stay, highlights include a comfortable king bed, a quiet setting, a cozy fireplace, and the large ground floor bathroom that feels like your own spa- we thoroughly enjoyed the sauna, huge bathtub, and rain shower. Ron was a great host and was very responsive with any questions we had. We spent many hours watching TV on the screen and projector set up, we grabbed more pillows from upstairs to add some more cushion to the leather couch downstairs.

So hyggelig! Hygge House is 100% what it promises. Wonderful, peaceful place to escape the busy life for a few days and relax in a beautiful house in a beautiful forest. Hot tub, sauna, cosy house, surrounded by nature. Near all activities of Stratton area. We even got five inches of new snow making it winter wonderland in April.

This was such a relaxing home to spend a celebratory weekend in! We had a great time at Adnan's home over the weekend. The setting is so peaceful, right on the water and we enjoyed the fire pit one evening. The space is large, with plenty of room for all. The house is a little bit dated, but with that said, it had everything we needed for a lake-weekend! On top of that, Adnan could not have been more accommodating and responsive.

Lovely and relaxing stay. Easy to find and very clean. We loved using the kayaks too!

My family and I booked this place for a relaxing weekend to unplug and we got just that! The kitchen had everything we needed, the couches were extremely comfortable, and the view was great! We would love to come back again soon.

This place is amazing and top notch! The perfect house in the perfect location, with a wonderful host - TJ outdid himself! TJs house is spotless with so much room for families/large groups, and the views are breathtaking. The fire-pit, kids play area - every detail was thought of and we couldn’t appreciate it more. Drinking my morning coffee on the master balcony while looking at the lake, I can’t wait to come back! We are already planning our next stay here. I would highly recommend anyone to stay here! Thanks TJ!

We had a great time at the Chalet, and all the extra touches were appreciated. Plenty of towels, available firewood, kcups for coffee and many other extra touches. We did a lot of cooking, and kitchen was stocked with dishes, pots and pans, etc. Great location. When not enjoying Lake Sacandaga, Saratoga and Lake George are also close by to visit. We would definitely stay here again!

Great place for families, there is a lot of room and toys for kids, and the lake is just a short walk away!

Great stay away from busy nyc. Private and warm

Really good home. Great location for relaxing and being on the water. The lake was slightly frozen but, it was still amazing.