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.

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Guest favorite

An expansive deck is surrounded by lush greenery, featuring outdoor seating and a dining area. Warm café lights hang overhead, creating a cozy atmosphere. A person is seen grilling at a gas grill, while another enjoys a meal at a table, capturing a serene outdoor experience.

Chalet in Otis

4.95 out of 5 average rating, 411 reviews

Mid-Century Glass Octagon in the Berkshires

AishwaryaRating, 5 stars3 weeks ago

Katherine's home is absolutely stunning. It is very thoughtfully put together and has the most welcoming vibe. We were there for the weekend and it was one of the most peaceful getaways that allowed us to connect with ourselves and our creativity. I would recommend this Airbnb to everyone. We will definitely be booking this stay again :)

Top guest favorite

A spacious deck is surrounded by lush greenery, featuring a large wooden dining table complemented by chairs. The design allows for an unobstructed view of the trees, enhancing the serene outdoor experience. Glass panels provide a sense of openness and connection to nature.

Chalet in Charlemont

4.99 out of 5 average rating, 71 reviews

StrautmanHaus: All-Season Chalet at Berkshire East

JRating, 5 stars2 months 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!

Top guest favorite

A serene view of Packard Pond is framed by lush green trees. The calm water reflects the sky and surrounding landscape, while a floating dock is positioned in the foreground. The tranquil scene invites relaxation and connection with nature.

Chalet in Orange

5 out of 5 average rating, 27 reviews

Spectacular Lakefront 3br House, AC, private beach

DonnaRating, 5 stars6 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.

Superhost

A spacious living area features high ceilings and large windows that allow natural light to fill the room. A wood stove stands against a stone wall, and various seating options are provided, complemented by layered rugs. Bookshelves are visible in the background, adding a cozy touch.

Chalet in Lenox

4.82 out of 5 average rating, 22 reviews

Peaceful Chalet in the Woods: Walk to Lenox

DanielaRating, 5 stars2 months ago

Simeon and Anna's place is beautiful! They made me feel right at home. My stay was amazingly peaceful which is exactly what I was looking for. the chalet is centrally located so everything is easy to get to. I recommend this place to anyone sifting through Airbnb listings, you will not be disappointed. beautiful place beautiful setting, and very convenient! I will be back! Thank you, Simeon and Anna, for sharing such an awesome place.

Top guest favorite

Chalet in Charlemont

4.99 out of 5 average rating, 99 reviews

The Lodge on Warner Hill

MichaelRating, 5 stars1 week ago

The house was an amazing retreat, which our family truly enjoyed for our Easter festivities. Michelle was kind enough to extend our stay due to the holiday which was so appreciated. The house is in fantastic shape, with all of the amenities that you would ever need. We would surely choose her house again for our next family gathering.

Guest favorite

A cozy loft area features a plush armchair positioned near large triangular windows. Natural light floods the space, highlighting the warm wood paneling of the sloped ceiling. A small table with a book is nearby, creating a perfect spot for relaxation.

Chalet in Otis

4.9 out of 5 average rating, 63 reviews

Kayaks, Sauna & Family: Relax & Play

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.

Guest favorite

Chalet in New Marlborough

4.92 out of 5 average rating, 53 reviews

Modern 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!

Guest favorite

An open concept great room features high cathedral ceilings and large windows allowing natural light to fill the space. A dining table is positioned near the kitchen, with seating for several. Comfortable seating surrounds a media area, creating a welcoming atmosphere for relaxation.

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.

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Popular amenities for Massachusetts chalet rentals

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Family-friendly chalet rentals

Guest favorite

A spacious great room features high ceilings with wooden beams and large triangular windows. A wooden dining table is situated near the windows, while comfortable seating arrangements with neutral-toned upholstery are arranged around a central fireplace. Natural light fills the space, enhancing the open concept design.

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 favorite

A chalet-style home is situated on a forested property, with a spacious deck extending from the front. Large windows reflect the surrounding greenery, showcasing a modern aesthetic against a backdrop of autumn foliage. Rock formations and scattered leaves cover the ground.

Chalet in Peru

4.92 out of 5 average rating, 284 reviews

Swiss Chalet Style Timberframe Home in Berkshires

LauraRating, 5 stars1 month 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 favorite

A modern kitchen is presented with sleek, dark cabinetry and stainless steel appliances. A large window provides natural light, while a geometric light fixture hangs overhead. The open design features a view into the living space, showcasing a blend of stone and wood elements.

Chalet in New Marlborough

4.92 out of 5 average rating, 53 reviews

Modern 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!

A patio area overlooks the serene lake, featuring lounge chairs with striped cushions and a wooden dining table. A striped umbrella provides shade, while lush greenery and calm waters are visible in the background, enhancing the outdoor setting.

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 favorite

A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.

Chalet in Otis

4.95 out of 5 average rating, 411 reviews

Mid-Century Glass Octagon in the Berkshires

AishwaryaRating, 5 stars3 weeks ago

Katherine's home is absolutely stunning. It is very thoughtfully put together and has the most welcoming vibe. We were there for the weekend and it was one of the most peaceful getaways that allowed us to connect with ourselves and our creativity. I would recommend this Airbnb to everyone. We will definitely be booking this stay again :)

Top guest favorite