Chalet holiday rentals in The Berkshires

The house is so beautiful and unique, and there is art everywhere you look. It inspires creativity! The hot tub and pool are incredible. The house has everything you need to feel at home. It's quiet and peaceful, and the view is out of this world. This is such a wonderful place for a getaway. Our family had a great time, and we can't wait to visit again soon! Olia made sure we had everything we needed and provided great suggestions for things to do in the area. It was an amazing holiday getaway!

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

Stop scrolling, you found your next vacation. Bob is a fantastic host with a stunning home. We have stayed with Bob many times and he continues to invest in the property and ensures your stay is nothing short of fantastic. Cannot recommend the ski chalet enough.

This place was lovely! Super cozy, very well decorated, and hosts a wonderful view! Judi’s was kind, understanding, responsive, and all around a wonderful host. We came here for a friend’s birthday and he was blown away. Thank you for everything, and we plan to come again soon!

Great location! This was a two family trip up to Mt Snow. We had a wide range of ages and 2 dogs. The house had plenty of toys and things for the kids to do - their favorite was the scavenger hunt! The kitchen is one of the best stocked kitchens compared to other Airbnbs we have used. The beds were comfortable - plenty of extra pillows and blankets. The couch and chairs in the living area were also very comfortable. The hot tub was very nice and enjoyable after everyone went skiing.

Needed a home-base for the weekend and Mary’s place was once again (this was our second stay here!) fantastic. Waking up to the sound of the river in the yard from the rainstorm the day before is incredibly special.

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.

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

This Airbnb in the Catskills was absolutely perfect, especially for such a special weekend—we got engaged in the area and couldn’t have asked for a better place to come back to and celebrate! The house is beautiful, with a stunning backyard, an amazing hot tub, and a basement full of games that kept everyone entertained. There were plenty of beds, so it was super comfortable for our group. Stephanie was incredible—she made everything so easy and was super responsive anytime we needed anything. You can tell she puts so much thought into making sure guests have a great experience. This is honestly the best Airbnb I’ve ever stayed at. It felt like a mix of cozy and fun, with everything we needed to make the weekend unforgettable. Hoping to come back in the future!

I spent a week at Fouz and Chris's place with my family (8 adults, a toddler and two dogs) and we had very relaxing, enjoyable, comfortable stay. The house is in a quiet, private area and a short distance from places of interest for hikes, restaurants, museums, historical sites, etc. We received great recommendations from the hosts.

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.

Josh was very responsive and accommodating throughout our stay. The home was beautiful, clean, and comfortable — we would definitely stay again!

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!

The house was spacious, clean, beautiful and private. We loved the view of Windham Mt from the second floor! The fireplace, expansive but cozy couch and downstairs game room were a hit! Half of my family skied and half stayed at the house to relax. Being 5 minutes from the mountain was fantastic and the house was perfect. Great restaurants nearby, where we had lunch, but the rest of the time we cooked in. Well equipped open kitchen! Hope to be back many times!

We really enjoyed our stay; the house was ideally situated in a private, wooded area and yet just a few minutes drive into Manchester. The views from the house were spectacular. The house had a cozy mountain chalet feel and yet equipped with a very modern kitchen. We took advantage of both the fire pit and the hot tub.

Our family and friends took a trip to Mount Snow skiing and when I came across Tommy’s house it was everything we were looking for. The house was just as described, location was perfect and so was the house. Tommy was right there to help with any questions we had and was a real pleasure to work with. I would highly recommend this house to anyone!

Our group at a great time at Nataliya’s in Hunter! The lake was absolutely the highlight, we made full use of the kayaks. Hunter itself is a little sleepy even when we went in May but we enjoyed exploring it and nearby Leeds and Tannersville.

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.

Our stay at Patti’s chalet was incredible! The home itself is beautiful and the view of the lake is breathtaking. It is a very quiet and peaceful neighborhood, which we enjoyed walking around every morning. It is also conveniently located—only 20 minutes to downtown Keene. The home is clean and boasts modern amenities. Our favorite features were the decks, fireplace, spacious kitchen, comfy couch, and the game room. The arcade and foosball table were so much fun. This stay was the perfect combination of rest, relaxation and fun. Patti was a very responsive host. We would definitely stay again!

I had an amazing stay at this cozy retreat in the Catskills! The house was exactly as described and more—clean, well-equipped, and tucked away in a peaceful, scenic location. Waking up to the sounds of nature and sipping coffee on the porch was the perfect way to start each day. The host was incredibly responsive and thoughtful, providing quick responses and making check-in a breeze. Whether you're looking to hike, unwind by the fire pit, or just enjoy the quiet beauty of the mountains, this place is ideal. Highly recommend for anyone looking to escape the city and recharge in nature. I’ll definitely be coming back!

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!

3rd times the charm!!! This was 3rd straight year myself & my crew(family), plus Charlie(Golden Retriever) have been to Alyson & Rob's house! Even though Mother Nature wasn't on our side all weekend, we still had an awesome weekend! Daytime down by the lake, then spending nights around the fire with a few cocktails is a great weekend! Rob & Alyson are quick with a reply to any questions! Looking forward to next year for Round 4! Highly recommend!