
Chalet holiday 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
Holiday 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 favourite

Chalet in Richmond
4.97 out of 5 average rating, 93 reviewsUpdated Berkshires Chalet Mins to Tanglewood/Lenox
GlennRating, 5 stars7 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, 284 reviewsSwiss Chalet Style Timberframe Home in Berkshires
LauraRating, 5 stars3 weeks ago
This is my favorite rental. It is so cozy and open at the same time. There is plenty of space for everyone with two twin beds, a king bed in the loft, a fold out sofa and a queen bedroom downstairs for my daughter. The woods are beautiful and the house is in a quiet location. At the same time, it is not too far from the Allendale shopping area in Pittsfield, small stores in Hinsdale, as well as Williamsburg and Northampton. The house is very warm even in the winter, comes with everything you need to cook, and has laundry. The bedrooms are comfortable and bathrooms are nice. The TV and WIFI streaming work great. There is an extra long table which we use for games and a deck overlooking the backyard. Overall, it is a great place to stay for families.
Guest favourite

Chalet in New Marlborough
4.92 out of 5 average rating, 53 reviewsModern Secluded Ski Chalet | 40 Acres | Family
JustinRating, 5 stars7 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 stars7 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 Monterey
5 out of 5 average rating, 10 reviewsStunning Log Cabin with brand new Pickleball court
BethRating, 5 stars62 months ago
Absolutely beautiful and well maintained cabin. Professional kitchen, with all the things and every sort of glass you’d need for entertaining. Fireplace was so perfect on a cold night, game room downstairs was perfect for us - half of the group cozied up and watched a movie and the others played a friendly round or three of pool. Games galore so you’re never bored; it’s clear that anyone who stays here has a blast. Jacuzzi for a cold winter night was awesome and though the neighbors aren’t far you feel like you’re out in the middle of nowhere. And, you’re just about 15 mins from Great Barrington with all the shops and quaint Main Street. Perfect weekend getaway for our group.
Guest favourite

Chalet in Otis
4.95 out of 5 average rating, 409 reviewsMid-Century Glass Octagon in the Berkshires
MandyRating, 5 stars1 month ago
We had a peaceful 5- night getaway at Katherine’s. The bed was one of the most comfortable I’ve ever slept on! The weather ranged from the 16 degrees on our first night to nearly 65 degrees on our last day - we were comfortable through all of it. And the views! The views from the octagon house are stunning, and instantly relaxing. The home is fully equipped with anything anyone could need. Chris at the Grouse House made us feel super welcome on our first night in Otis and we had great breakfasts at Paige’s Place right down the road (3 days in a row! Shout out to Eric!). We also found some other great places like Antimony Brewing in Lennox, and Agave’s in Great Barrington - both within a 30 minute drive. Thanks again for sharing your home!
Top Guest favourite

Chalet in Monterey
4.98 out of 5 average rating, 83 reviewsCozy 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 reviewsUpdated Berkshires Chalet Mins to Tanglewood/Lenox
GlennRating, 5 stars7 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
4.92 out of 5 average rating, 62 reviewsLake, Kayaks & Sauna - Family & Wellness
MegRating, 5 stars1 month ago
Clemence's place is gorgeous and comfortable! Perfect stay for our group of friends catching up for the weekend. Super clean, the kitchen is extremely well stocked - much better than shows in the photos or is listed in the description. Private spot with plenty of space. Had a lovely walk in a nearby state park, too.
Top Guest favourite

Chalet in Charlemont
4.99 out of 5 average rating, 71 reviewsStrautmanHaus: All-Season Chalet at Berkshire East
JRating, 5 stars1 month ago
Great stay slopeside at Berkshire East. We had a wonderful week and the house was perfect. We had some trouble with the weather (and power) that was out of host's hands but they went above and beyond to stay in touch and help get through it. Great spot for family skiing, or group trip mountain biking, rafting, etc. Thanks!

Chalet in Monterey
5 out of 5 average rating, 10 reviewsStunning Log Cabin with brand new Pickleball court
BethRating, 5 stars62 months ago
Absolutely beautiful and well maintained cabin. Professional kitchen, with all the things and every sort of glass you’d need for entertaining. Fireplace was so perfect on a cold night, game room downstairs was perfect for us - half of the group cozied up and watched a movie and the others played a friendly round or three of pool. Games galore so you’re never bored; it’s clear that anyone who stays here has a blast. Jacuzzi for a cold winter night was awesome and though the neighbors aren’t far you feel like you’re out in the middle of nowhere. And, you’re just about 15 mins from Great Barrington with all the shops and quaint Main Street. Perfect weekend getaway for our group.
Destinations to explore
- Waterfront rentals Massachusetts
- Fitness-friendly rentals Massachusetts
- Rentals with an accessible height toilet Massachusetts
- Boutique hotel rentals Massachusetts
- Rentals with outdoor seating Massachusetts
- Rentals with a fire pit Massachusetts
- Beach house rentals Massachusetts
- Rentals with a home theatre Massachusetts
- Pet-friendly rentals Massachusetts
- Rentals with a patio Massachusetts
- Rentals with a fireplace Massachusetts
- Mansion rentals Massachusetts
- Beachfront rentals Massachusetts
- Rentals with an accessible height bed Massachusetts
- Loft rentals Massachusetts
- Rentals with breakfast Massachusetts
- Guesthouse rentals Massachusetts
- Cottage rentals Massachusetts
- Barn rentals Massachusetts
- Townhouse rentals Massachusetts
- Luxury rentals Massachusetts
- Private suite rentals Massachusetts
- Rentals with an EV charger Massachusetts
- Rentals with a hot tub Massachusetts
- Kid-friendly rentals Massachusetts
- Tiny house rentals Massachusetts
- Rentals with pools Massachusetts
- Rentals with a sauna Massachusetts
- Family-friendly rentals Massachusetts
- Ski-in/ski-out rentals Massachusetts
- Lakehouse rentals Massachusetts
- Hotel rentals Massachusetts
- Apartment rentals Massachusetts
- Bungalow rentals Massachusetts
- Condo rentals Massachusetts
- Rentals with a kayak Massachusetts
- Cabin rentals Massachusetts
- House rentals Massachusetts
- Villa rentals Massachusetts
- Smoking-friendly rentals Massachusetts
- Rentals with lake access Massachusetts
- Rentals with a washing machine and dryer Massachusetts
- Bed and breakfasts Massachusetts
- Rentals with beach access Massachusetts
- Farmstay 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
- Art and culture Massachusetts
- Food and drink Massachusetts
- Tours Massachusetts
- Nature and outdoors Massachusetts
- Sightseeing Massachusetts
- Things to do United States
- Tours United States
- Nature and outdoors United States
- Entertainment United States
- Food and drink United States
- Wellness United States
- Sports activities United States
- Sightseeing United States
- Art and culture United States