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!

Beautiful place, real quaint and nice to stay at. The surroundings were real nice at nice and the nature was very nice to be surrounded by. All the amenities worked as expected and the beds were comfortable. The porch was our favorite place to relax at; hammock, yard, stereo playing from inside. Great stay … thanks Jason and Sara :))))

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

very cosy for friends of 4. There are so many details of arts and family history in the house, respect that!

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 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!

Family had a great stay at Danielle and Ben’s the house was very clean and kid friendly and we really enjoyed having the view of the creek from decking area. Very close to Mt Snow and surrounding area restaurants and attractions. Would stay again.

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.

Genesis is a wonderful host - very responsive and accommodating. The house was absolutely beautiful and we’d love to come back again sometime!

Had a small weekend trip away in the mountains. The group had a blast. The landscape was beautiful. It rained one night and snowed the next, so we spent a lot of time indoor; but the place is beautiful, and we definitely plan to come back in warmer weather for a longer time!

Rebecca and Curtis were wonderful hosts. The mountain view alone is worth every penny paid and the space was peaceful and beautiful. We are a family of 5 (2 adults, 1 child, 2 pets) and the rooms were very spacious and clean. We appreciated the quality of every detail, from the fire pit and outdoor dining table to the cookware. Most major amenities (supermarket, Walmart etc..) are 25 min away which was fine for us. We will be back again. Thank you, Rebecca and Curtis, for allowing us into your lovely space!

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.

We adored our stay! It was perfect for our group. The sauna and hot tub were a massive hit. The hosts are wonderful. On a stormy night we lost power and Josh quickly reached out to check-in give us power company updates and let us know the generator would do its thing which it did beautifully. Would love to come back with my family and enjoy further relaxing and peaceful moments together in the mountains!

The house was well stocked, neat and clean. The property has lots of great outdoor space to relax in. Nataliya was very responsive. Thank you.

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.

A beautiful, well-appointed, family-friendly place to stay. Teddy's place had everything we needed and more. The beds were comfortable, everything was clean and well maintained, and exactly as described and like the photos show.

This place housed 5 of us easily. Everything worked as it should, and was comfortable. Would recommend others to stay at this location. Very nice views.

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 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.