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Chalet holiday rentals in Massachusetts

Find and book unique chalets on Airbnb

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Popular amenities for chalet rentals in Massachusetts

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!
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 stars6 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!
Top guest favourite
Chalet in Orange
5 out of 5 average rating, 27 reviews

Spectacular Lakefront 3br House, AC, private beach

DonnaRating, 5 stars8 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, 104 reviews

The Lodge on Warner Hill

AllisonRating, 5 stars3 weeks ago
It was remote compared to the graduation we were attending in the area but we all felt worth the distance. Very comfortable, incredibly clean, well designed house. We had freezing weather so were not able to use the deck or fire pit area. Thank you, Michelle!
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.
Private room in Taunton

The Bay Chalet with Game Room and Bar

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