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Chalet holiday rentals in Berkshire County

Find and book unique chalets on Airbnb

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Popular amenities for chalet rentals in Berkshire County

Family-friendly chalet rentals

Guest favourite
Chalet in Richmond
4.97 out of 5 average rating, 93 reviews

Updated Berkshires Chalet Mins to Tanglewood/Lenox

GlennRating, 5 stars9 months ago
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.
Top guest favourite
Chalet in Peru
4.92 out of 5 average rating, 287 reviews

Swiss Chalet Style Timberframe Home in Berkshires

WilliamRating, 5 stars3 weeks ago
I had a wonderful stay at Laura’s place. The home is not only beautiful but thoughtfully constructed. Its exposed wood frame feels so natural and adds to the calming atmosphere. The backyard was clean, maintained, and offered a serene space to relax. Laura’s instructions were clear and made finding and settling into the house easy. The bedrooms and bathrooms were incredibly cozy and well-kept. Every detail made the space feel warm and welcoming. It’s also a fantastic spot for groups. Our group of six friends fit very comfortably, with plenty of space to relax and unwind. I’d absolutely recommend this home to anyone looking for a peaceful, comfortable getaway.
Guest favourite
Chalet in New Marlborough
4.92 out of 5 average rating, 53 reviews

Modern Secluded Ski Chalet | 40 Acres | Family

JustinRating, 5 stars9 months ago
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!
Chalet in Lee
4.83 out of 5 average rating, 65 reviews

Waterfront lakehouse in Berkshires

LorriRating, 5 stars9 months ago
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!
Chalet in Stephentown
5 out of 5 average rating, 13 reviews

Ski Cottage in the Berkshire hills

WendyRating, 5 stars34 months ago
A rustic, charming, and treehouse-like stay in the Berkshires. The house is not modern by any means but has a wonderful, well-loved, and lived-in feel. Elissa was an incredible host and very responsive. We really enjoyed exploring Jiminy peak, Cherry Plain State Park, rowing and swimming in the pond, exploring the Farmer's market in Troy, kayaking along the Hudson near Albany, and hiking to Kinderhook creek. Our family also enjoyed berry picking at Berry Patch Farms (and getting their CSA). I'm sure the trees here would be incredible in the fall. We were lucky enough to catch the Perseid meteor shower, Saturn, Jupiter, and the super moon while we were here. The Wifi was good enough for zoom calls but definitely would cut out whenever we used the microwave. All-in-all a lovely getaway and very close to hiking trails.
Guest favourite
Chalet in Otis
4.94 out of 5 average rating, 417 reviews

Mid-Century Glass Octagon in the Berkshires

ChelseaRating, 5 stars2 weeks ago
If you’re looking for a secluded area away from all the noise, this is the place! Katherine’s home was very peaceful and quiet. It was clean and I have no complaints at all. The WiFi was fast and my favorite part about this place is the projector. A great spot to watch movies! Katherine was a very responsive host and we felt right at home. I definitely recommend booking!
Top guest favourite
Chalet in Monterey
4.98 out of 5 average rating, 84 reviews

Cozy French Country chalet

JacobRating, 5 stars5 days ago
This place is great. Cozy, tucked away, peaceful, beautiful surroundings. Valerie is easy to communicate and quick to respond. The instructions were clear.

Luxury chalet rentals

Guest favourite
Chalet in Richmond
4.97 out of 5 average rating, 93 reviews

Updated Berkshires Chalet Mins to Tanglewood/Lenox

GlennRating, 5 stars9 months ago
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.
Guest favourite
Chalet in Otis
4.91 out of 5 average rating, 65 reviews

Kayaks, Sauna & Family: Relax & Play

CarlaRating, 5 stars1 month ago
Lovely stay in western MA. Well furnished home with all the comforts of home. Loved the screened in eating porch and spent a good amount of time sitting around the large table. We had a lot of fun using the amenities like the sauna. Since it was a but early in the season we didn't get out on the lake but enjoyed the view and relaxing in nature.
Guest favourite
Chalet in New Marlborough
4.92 out of 5 average rating, 53 reviews

Modern Secluded Ski Chalet | 40 Acres | Family

JustinRating, 5 stars9 months ago
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!
Chalet in Hillsdale
5 out of 5 average rating, 3 reviews

Catamount Family Retreat - Walk to the Slopes

AlexandraRating, 5 stars3 weeks ago
Great house, perfect for our family. We stayed in the summer and it rained the whole time, but we still enjoyed it. The road is not very safe to walk on so definitely need a car to get around, but the restaurant right across the street at Little Cat was great. Overall really good place to stay, will be back
Chalet in Monterey

New Listing - Fully Renovated Lake/Ski Chalet

SuzannaRating, 5 stars3 months ago
This is a great house in a nice location. It’s comfortable, warm, well stocked kitchen, the jacuzzi was a nice touch have. Garry was a good host who was responsive and easy to work with.

Destinations to explore