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Chalet vacation rentals in Western Massachusetts

Find and book unique chalets on Airbnb

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Popular amenities for Western Massachusetts chalet rentals

Family-friendly chalet rentals

Superhost
An outdoor deck is featured, with Adirondack chairs arranged around a circular table. Lush greenery surrounds the area, and a scenic view of the Harriman Reservoir is visible in the distance under a partly cloudy sky.
Chalet in Readsboro
4.85 out of 5 average rating, 320 reviews

The King's Cottage

JaskeeratRating, 5 stars2 months ago
Had an amazing time her with my friends. Very clean place and super nice cabin in the woods. Make sure you have a 4wd drive car in the winter to get up the driveway.
Top guest favorite
Chalet in Catskill
4.96 out of 5 average rating, 190 reviews

Daydream Mountain Art-Chateau | Hot Tub & Pool

MonikaRating, 5 stars1 week ago
This was our second year staying here with friends, and we had such a lovely time. There's plenty to do inside the house itself even on a dreary day, with curiosities and art abound, instruments, games, fireplace, etc, a great kitchen for group meals, and spacious and comfortable rooms otherwise. Olia is very kind and responsive, with plenty tips for the local area. We'd recommend for groups or families in an instant. Nothing like relaxing in the hot tub while looking out at the mountain vista with rain pattering on the porch roof above - pure bliss.
Guest favorite
A gravel driveway leads toward a charming wooden house surrounded by trees in autumn foliage. Greenery and colorful leaves create a welcoming entrance as the home is partially visible in the background.
Chalet in Wilmington
4.95 out of 5 average rating, 98 reviews

Rustic Sunny Vermont Home near Mount Snow

AndreaRating, 5 stars1 month ago
Couldn't say enough great things about both the hosts and the property. Just lovely home - very spacious, and clean and cosy. The area is gorgeous, with a lot to do. Mt. Snow and Hermitage skiing are very close, and Wilmington and the area are charming. Host was very gracious and kind..thank you!
Superhost
The exterior of the chalet features large windows that allow natural light to fill the interior. A hot tub is situated on the deck, along with outdoor seating and a grill, surrounded by tranquil wooded views.
Chalet in Hunter
4.7 out of 5 average rating, 156 reviews

Cozy Art Chalet | Hot Tub, Ski & Hike Escape

MathewRating, 5 stars3 months ago
An awesome place for a ski getaway! The house is beautiful, and just down the road from the mountain. Would highly recommend!
Guest favorite
The kitchen features an open layout with bright natural light illuminating modern appliances, a spacious island with seating, and rustic shelving displaying various kitchen essentials. A solid wood dining table sits in the background, complemented by a patterned rug beneath.
Chalet in Jewett
4.97 out of 5 average rating, 182 reviews

Private Catskills Home w. Hot Tub, near Ski Mnt

Gina-LouiseRating, 5 stars2 months ago
Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!
Superhost
Chalet in Jamaica
4.78 out of 5 average rating, 444 reviews

Chalet 7min to Ski Stratton-WoodStove,Views,DogsOK

BrennanRating, 5 stars1 day ago
The quiet retreat in Vermont, just like we wanted. We are already comfortable with country living, so being here was easy and peaceful.
Guest favorite
A contemporary home is set amidst vibrant autumn foliage, showcasing a blend of warm wood tones and large windows. The grassy area in front invites relaxation, while the surrounding trees enhance the rustic charm of the property.
Chalet in Elka Park
4.9 out of 5 average rating, 596 reviews

Secluded home by Hunter Mountain

RylieRating, 5 stars1 week ago
Had a lovely time! It’s a beautiful house and Juris sent very clear and helpful instructions before check in. Would stay again.
Top guest favorite
A well-lit hallway features three doorways leading to different rooms. Soft, neutral-colored walls are complemented by a plush, light-colored rug covering the floor. One doorway opens to a cozy blue room, while two others remain closed, adding to the sense of privacy and space.
Chalet in Hensonville
4.96 out of 5 average rating, 359 reviews

2BDR- Cozy Windham/Hunter Escape

AmyRating, 5 stars1 month ago
Such a great and cozy stay! Minutes from town center and Windham, so easy to check in / check out. Very happy we stayed here!

Luxury chalet rentals

Guest favorite
An entrance features a wood-beamed ceiling supported by sturdy columns, creating a welcoming space. A stone path leads to a large wooden door, complemented by a decorative wind chime and a serene sculpture. Natural light filters through the adjacent windows.
Chalet in Mount Tremper
4.98 out of 5 average rating, 107 reviews

Modern Mountain Chalet on 15 Acre Catskills Estate

JonathanRating, 5 stars2 months ago
Lovely stay with family and friends. The host went out of his way to ensure our arrival was smooth, even with a very icy driveway and up to two inches of snow falling. The space is beautiful, secluded and serene. But also close to restaurants in Mt. Tremper and good hikes.
Guest favorite
Chalet in West Dover
4.98 out of 5 average rating, 50 reviews

Charming Chalet w. Hot Tub - 1 Mile to Mt. Snow

LaurenRating, 5 stars1 week ago
A beautiful spot perched amongst the trees and snowy woods. Cosy couches and fireplaces, a magical hot tub and generous touches, like extra wood, coffee and shampoo. I took my boys skiing nearby and we all loved every minute. Wouldn't hesitate to stay again
Guest favorite
Chalet in Dover
4.93 out of 5 average rating, 44 reviews

New! Custom Chalet minutes from Mt Snow w/ Hottub

ZacharyRating, 5 stars2 months ago
The house was fantastic. Great condition, cool layout! There was a ton of snow, and the property was well plowed, shoveled and sanded!
Superhost
Chalet in Dover
4.65 out of 5 average rating, 31 reviews

Mount Snow Chalet w/ Ski-Home Trail & Indoor Sauna

CarolRating, 5 stars2 months ago
The house was super close to the mountain The house had everything you could possibly need in the kitchen Three living rooms which was nice we were unable to turn the sauna on sadly Perfect ski house entrance with a lot of room the take everything off without tracking into the rest of the house Large table to eat and play games on I would definitely stay here again
Guest favorite
A wooden exterior of a mountainside retreat is framed by lush greenery. The porch features wooden steps leading to a seating area with chairs. Tall trees and shrubs create a natural border around the property, enhancing the tranquil setting.
Chalet in Mount Tremper
4.98 out of 5 average rating, 145 reviews

Secluded Woodstock Retreat with Pool and Sauna

BarryRating, 5 stars2 months ago
My wife and I stayed at Ron’s place for five nights for a winter getaway. We had a great stay, highlights include a comfortable king bed, a quiet setting, a cozy fireplace, and the large ground floor bathroom that feels like your own spa- we thoroughly enjoyed the sauna, huge bathtub, and rain shower. Ron was a great host and was very responsive with any questions we had. We spent many hours watching TV on the screen and projector set up, we grabbed more pillows from upstairs to add some more cushion to the leather couch downstairs.
Guest favorite
A rustic treehouse is elevated among the trees, featuring an open deck and enclosed area. Surrounded by lush greenery, the structure offers a serene retreat in the forest, inviting guests to immerse themselves in nature.
Chalet in Stratton
4.96 out of 5 average rating, 131 reviews

Luxe HOT TUB, SAUNA 8–12 min Stratton & Mount Snow

TimoRating, 5 stars1 week ago
So hyggelig! Hygge House is 100% what it promises. Wonderful, peaceful place to escape the busy life for a few days and relax in a beautiful house in a beautiful forest. Hot tub, sauna, cosy house, surrounded by nature. Near all activities of Stratton area. We even got five inches of new snow making it winter wonderland in April.
Guest favorite
Chalet in Gardiner
4.95 out of 5 average rating, 184 reviews

Modern Zen Chalet at the Foot of Gunks w Mt. View

GerryRating, 5 stars1 week ago
Spent two nights at this lovely property. For me it's perfect, spacious and remote but still in a great location. You're close to everything, have a beautiful home and outdoor space to enjoy, and Serg/Aaron are extremely helpful with anything you might need. Highly recommend and loved my stay 👍
Guest favorite
A spacious four-bedroom house is presented against a snowy landscape, showcasing a combination of wooden shingles and stone. Large windows provide ample natural light, while multiple balconies offer outdoor seating. The property is surrounded by protective stone walls and wooded views.
Chalet in Windham
4.88 out of 5 average rating, 189 reviews

Beautiful Windham Ski/Summer House

AmyRating, 5 stars2 months ago
The house was spacious, clean, beautiful and private. We loved the view of Windham Mt from the second floor! The fireplace, expansive but cozy couch and downstairs game room were a hit! Half of my family skied and half stayed at the house to relax. Being 5 minutes from the mountain was fantastic and the house was perfect. Great restaurants nearby, where we had lunch, but the rest of the time we cooked in. Well equipped open kitchen! Hope to be back many times!

Lakefront chalet rentals

Guest favorite
A serene waterfront scene is captured, showcasing calm, reflective waters framed by lush greenery. A cozy seating area with striped cushions is positioned nearby, inviting relaxation. In the distance, a family enjoys time on the water while the sun filters through the trees.
Chalet in Antrim
4.94 out of 5 average rating, 95 reviews

Direct Waterfront A-Frame, Close to 3 Ski Areas!

SheriRating, 5 stars1 week ago
What a great lake house! My family and I went up with the dogs and had such a great time. The place was child friendly, dog friendly, the host was responsive, the hot tub was relaxing, and the view was beautiful. Although we went up when the weather was still too cold to go swimming, the hot tub made for a relaxing evening. This place had everything we were looking for. Thank you
Guest favorite
An outdoor deck is shown with a relaxing lounge area, featuring wooden chairs and a grill. A hot tub is positioned to one side, while a fire pit sits in the center. The serene lake view is framed by trees, creating a peaceful setting.
Chalet in Hunter
4.98 out of 5 average rating, 152 reviews

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE

ChristinaRating, 5 stars2 weeks ago
This place was perfect for our Mom’s Book Club Retreat. The living room was spacious enough for all 7 of us but still so cozy for chatting and reading (we were looking at tags to buy the same couches). The weather was terrible so we didn’t get to enjoy the outdoor spaces as much as we’d like but the hot tub and fire pit were great. The kitchen had everything we needed to cook all our meals . Communication and check in were a breeze. Would definitely recommend this place!
A serene view of the lake is captured, showcasing calm waters bordered by lush greenery. A wooden dock extends into the water, with a ladder visible for easy access. The surrounding yard is spacious, with well-maintained grass and a few decorative stones near the shore.
Chalet in Lee
4.83 out of 5 average rating, 65 reviews

Waterfront 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!
Guest favorite
A serene lakeside area is presented, featuring four wooden Adirondack chairs arranged around a pebble-strewn fire pit. A wooden dock extends into the calm water, with lush greenery surrounding the peaceful setting.
Chalet in Athens
4.86 out of 5 average rating, 49 reviews

Large & Sunny Lakefront Home-kayaks/fire pit/games

KatieRating, 5 stars4 days ago
This was such a relaxing home to spend a celebratory weekend in! We had a great time at Adnan's home over the weekend. The setting is so peaceful, right on the water and we enjoyed the fire pit one evening. The space is large, with plenty of room for all. The house is a little bit dated, but with that said, it had everything we needed for a lake-weekend! On top of that, Adnan could not have been more accommodating and responsive.
Guest favorite
Chalet in Athens
4.89 out of 5 average rating, 102 reviews

Waterfront Lake Home, close to Hunter & Windham

ShelbyRating, 5 stars7 months ago
Lovely and relaxing stay. Easy to find and very clean. We loved using the kayaks too!
Superhost
The exterior of the chalet is showcased, highlighting a two-story structure with a large deck. Wooden railings surround the deck, and boulders are integrated into the landscaping. Tall trees frame the home, providing a natural backdrop.
Chalet in Winchester
4.85 out of 5 average rating, 118 reviews

Chalet Sonsie: A Sweetwater Stay

KatieRating, 5 stars1 month ago
My family and I booked this place for a relaxing weekend to unplug and we got just that! The kitchen had everything we needed, the couches were extremely comfortable, and the view was great! We would love to come back again soon.
Guest favorite
Chalet in Sunapee
4.94 out of 5 average rating, 80 reviews

Lake Sunapee Get Away

WyattRating, 5 stars2 months ago
Carl was a great host and extremely responsive. He helped make the check in/out process extremely easy and was extremely responsive with any questions. There was snow shovels and salt to deal with snow which was helpful. He helped navigate an issue right away and was very generous with offering help even though he was somewhat unavailable. The house was a great location and very clean, and could accommodate a large group easily. The open floor plan for the kitchen/dining room/living room was very nice and we enjoyed the new range for cooking. Carl even helped to make sure we forgot something that we left at the house after contacting us that it was there! Overall, I would highly recommend staying here.
Superhost
The exterior of Maple Lodge showcases a modern grey house surrounded by greenery. A large deck features seating around a fire pit, while a children's play structure adds to the yard's charm. Ample parking is available in the gravel area beside the home.
Chalet in Lanesville
5 out of 5 average rating, 4 reviews

Maple Lodge - Luxury Cabin

CrystalRating, 5 stars2 weeks ago
This place is amazing and top notch! The perfect house in the perfect location, with a wonderful host - TJ outdid himself! TJs house is spotless with so much room for families/large groups, and the views are breathtaking. The fire-pit, kids play area - every detail was thought of and we couldn’t appreciate it more. Drinking my morning coffee on the master balcony while looking at the lake, I can’t wait to come back! We are already planning our next stay here. I would highly recommend anyone to stay here! Thanks TJ!

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