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Chalet holiday rentals in Massachusetts

Find and book unique chalets on Airbnb

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Popular amenities for Massachusetts chalet rentals

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 stars8 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, 285 reviews

Swiss Chalet Style Timberframe Home in Berkshires

JonathanRating, 5 stars1 week ago
I stay at laura's house every year in the spring, and I look forward each year to my visit in the berkshires. Laura's home is wonderful and the nature in the area is amazing. Would recommend to anyone to stay there!
Guest favourite
Chalet in New Marlborough
4.92 out of 5 average rating, 53 reviews

Modern Secluded Ski Chalet | 40 Acres | Family

JustinRating, 5 stars8 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 stars8 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!
Guest favourite
Chalet in Otis
4.95 out of 5 average rating, 413 reviews

Mid-Century Glass Octagon in the Berkshires

DavidRating, 5 stars2 weeks ago
My wife and I took a hiking trip in the Berkshires to celebrate her 40th birthday - we ended up staying in the Glass Octagon and had an incredible time. Katherine was a great host and incredibly responsive. The house was cozy and had everything we needed during our stay - the nature views from the cabin were also great! The location was secluded but also just close enough to local amenities, restaurants, stores etc. (i.e Paige’s Place was a great breakfast place only a short drive down the street.) We did a lot of traveling to Great Barrington which was conveniently only 20 minutes away from the Airbnb. We had a really great, relaxing time and would definitely consider staying here again. We would highly recommend it.
Top Guest favourite
Chalet in Monterey
4.98 out of 5 average rating, 83 reviews

Cozy French Country chalet

NoamRating, 5 stars2 months ago
Always so great. Thanks so much. A wonderful house and a wonderful host.

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 stars8 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, 64 reviews

Kayaks, Sauna & Family: Relax & Play

CarlaRating, 5 stars5 days 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 stars8 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!
Top Guest favourite
Chalet in Orange
5 out of 5 average rating, 27 reviews

Spectacular Lakefront 3br House, AC, private beach

DonnaRating, 5 stars7 months ago
OMG Beautiful! Walking into the gorgeous house, we didn't know whether to look inside or outside first! The inside is lovely, clean and neat without unnecessary clutter. The outside is spacious and beautiful. The house and property were described perfectly. Washer & dryer worked well. The pool table downstairs could easily be used without waking anyone in the house. When the owner learned we would be traveling with an infant, she made sure to have a highchair, crib, and infant life jacket in the house. The house is safe for babys. There isn't space to list all that we loved about this house. It has become part of our reunion week wonderful memories. Did I mention that the house was spotless and the grounds immaculate (except for the falling leaves which was part of the beauty!) I would happily stay here again and again and again.
Top Guest favourite
Chalet in Charlemont
4.99 out of 5 average rating, 101 reviews

The Lodge on Warner Hill

MichaelRating, 5 stars1 week ago
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!

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