
Chalet vacation rentals in Massachusetts
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Massachusetts
Guests agree: these chalets are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Massachusetts chalet rentals
Family-friendly chalet rentals
Guest favorite

Chalet in Richmond
4.97 out of 5 average rating, 93 reviewsUpdated 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 favorite

Chalet in Peru
4.92 out of 5 average rating, 287 reviewsSwiss Chalet Style Timberframe Home in Berkshires
WilliamRating, 5 stars4 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 favorite

Chalet in New Marlborough
4.92 out of 5 average rating, 53 reviewsModern 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 reviewsWaterfront 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 favorite

Chalet in Otis
4.94 out of 5 average rating, 418 reviewsMid-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 favorite

Chalet in Monterey
4.98 out of 5 average rating, 84 reviewsCozy French Country chalet
JacobRating, 5 stars1 week 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 favorite

Chalet in Richmond
4.97 out of 5 average rating, 93 reviewsUpdated 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 favorite

Chalet in Otis
4.91 out of 5 average rating, 65 reviewsKayaks, 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 favorite

Chalet in New Marlborough
4.92 out of 5 average rating, 53 reviewsModern 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!
Guest favorite

Chalet in Orange
5 out of 5 average rating, 27 reviewsSpectacular 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 favorite

Chalet in Charlemont
4.99 out of 5 average rating, 104 reviewsThe Lodge on Warner Hill
AllisonRating, 5 stars4 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!

Private room in Taunton
The Bay Chalet with Game Room and Bar
Destinations to explore
- House rentals Massachusetts
- Villa rentals Massachusetts
- Beach house rentals Massachusetts
- Waterfront rentals Massachusetts
- Rentals with a patio Massachusetts
- Rentals with an accessible height toilet Massachusetts
- Rentals with lake access Massachusetts
- Apartment rentals Massachusetts
- Rentals with an accessible height bed Massachusetts
- Loft rentals Massachusetts
- Fitness-friendly rentals Massachusetts
- Rentals with a sauna Massachusetts
- Pet-friendly rentals Massachusetts
- Beachfront rentals Massachusetts
- Cottage rentals Massachusetts
- Barn rentals Massachusetts
- Serviced apartment rentals Massachusetts
- Family-friendly rentals Massachusetts
- Lakehouse rentals Massachusetts
- Luxury rentals Massachusetts
- Rentals with beach access Massachusetts
- Rentals with a washer and dryer Massachusetts
- Bungalow rentals Massachusetts
- Rentals with a fire pit Massachusetts
- Smoking-friendly rentals Massachusetts
- Private suite rentals Massachusetts
- Kid-friendly rentals Massachusetts
- Tiny house rentals Massachusetts
- Boutique hotel rentals Massachusetts
- Rentals with a hot tub Massachusetts
- Cabin rentals Massachusetts
- Rentals with outdoor seating Massachusetts
- Rentals with breakfast Massachusetts
- Rentals with a fireplace Massachusetts
- Mansion rentals Massachusetts
- Bed and breakfasts Massachusetts
- Rentals with a home theater Massachusetts
- Guesthouse rentals Massachusetts
- Townhouse rentals Massachusetts
- Farmstay rentals Massachusetts
- Ski-in/ski-out rentals Massachusetts
- Rentals with an EV charger Massachusetts
- Hotel rentals Massachusetts
- Rentals with pools Massachusetts
- Rentals with a kayak Massachusetts
- Condo rentals Massachusetts
- Chalet rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do Massachusetts
- Tours Massachusetts
- Sightseeing Massachusetts
- Art and culture Massachusetts
- Nature and outdoors Massachusetts
- Food and drink Massachusetts
- Things to do United States
- Sports activities United States
- Nature and outdoors United States
- Art and culture United States
- Wellness United States
- Tours United States
- Food and drink United States
- Sightseeing United States
- Entertainment United States