Chalet vacation rentals in Western Massachusetts

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.

We had an issue with our previous rental and needed to find a place to stay that is pet friendly and available. Rad and Carol responded quickly to our reservation request. The house was made available to us early in the day and hot tub prepped last minute for us to enjoy! The Chalet is beautiful and spacious, the location is private and relaxing. The wood stove kept us warm and cozy while we enjoyed watching light snow fall. We would definitely stay there again and bring our family with us!

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!

This is my third time staying at Juris' fantastic home. It is an ideal accomodation to escape from the city when you want to unplug and reconnect with friends and nature. It is also very close to some very fun trails and a short drive to great restaurants and other happenings. Will definitely be coming back.

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.

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.

My friends and I had a wonderful stay at this Airbnb! The space was impeccably clean, making us feel right at home from the moment we arrived. It was incredibly quiet and peaceful, perfect for relaxing and unwinding. The surroundings were rustic and beautiful, adding to the overall charm of the stay. The host was thoughtful and attentive, ensuring everything was perfect. I highly recommend this place to anyone looking for a serene and spotless getaway!

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 a great stay at Genesis’s place! It was exactly as described: clean, cozy, and comfortable. We especially loved the location - it was peaceful and scenic, and just a short drive to Hudson, where we enjoyed some fantastic restaurants and shops. The mattresses were super comfortable, which made our stay even more relaxing. Would definitely recommend to everyone. Thank you, Genesis!

Beautiful home, even better in person! Clean and cozy. Each room was stylishly and uniquely decorated. Great for large groups.

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.

Amazing house. Took my son for his 2nd birthday. They had a travel crib and a high chair ready for us. The house was clean and smelt amazing. They have everything you could think of in the kitchen to make your stay feel like home. Fee coffee with cream and sugar. They even had tea! The hot tub was wonderful clean and well maintained. We were so happy to make memories here on my boys birthday! Thank you again we will be back!

Such an amazing house! It was close distance to Mt. Snow (15 min-ish), but off the beaten path enough for some peaceful R&R. Would love to come stay in the summer season too and use the grill and use the sweet fire pit on the deck! Beds were comfortable, house was clean and the kitchen has everything you could need. The Sonos sound system was the cherry on top! I can't say enough good things about the hosts; kind, friendly and very responsive. Thank you again!

What an absolutely wonderful experience! Emily was beyond caring and friendly, and I truly enjoyed every minute at this cabin. The water is beautiful, and the cabin was always cozy. I especially loved the beautiful kitchen, it was a dream! I highly recommend anyone to visit, definitely worth it!

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.

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!

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.

Absolutely amazing stay!! So peaceful and relaxing. Not too much nearby, which honestly was a good thing - allowed us to relax and unwind from the every day grind! Our son, age 5, absolutely loved playing in the Arcade!! We got in some fishing on the dock and watched movies by the fireplace at night. Just stunning. Exactly what we needed as a small family. Could not have asked for anything more. We WILL be back again soon!

Carl was a great host and extremely responsive. He helped make the check in/out process extremely easy and was extremely responsive with any questions. There was snow shovels and salt to deal with snow which was helpful. He helped navigate an issue right away and was very generous with offering help even though he was somewhat unavailable. The house was a great location and very clean, and could accommodate a large group easily. The open floor plan for the kitchen/dining room/living room was very nice and we enjoyed the new range for cooking. Carl even helped to make sure we forgot something that we left at the house after contacting us that it was there! Overall, I would highly recommend staying here.

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!