Chalet vacation rentals in Western Massachusetts

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Top-rated chalet rentals in Western Massachusetts

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Guest favorite

Chalet in Dover

4.94 out of 5 average rating, 117 reviews

Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow

My super cozy mountain chalet 10 mins from Mount Snow is the perfect spot to host your Vermont vacation! Let the grownups cozy up by the wood-burning fireplace in the living room, while the kids hang out in the second living room and game room downstairs. With air hockey, shuffleboard, and poker table, they’ll be busy for hours. Hmmm….maybe the grownups will claim that space for themselves! After a long day on the slopes or trails, the sauna, hot tub, or jacuzzi tub will feel great on tired musc

Guest favorite

Chalet in Otis

4.95 out of 5 average rating, 382 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Guest favorite

Chalet in Gilboa

4.98 out of 5 average rating, 132 reviews

Luxurious Chalet with Amazing Views Near Windham

Located just seven miles from Windham Mountain, this newly constructed 3-bedroom/4-bed/2-bath log-built chalet is a favorite amongst skiers and nature-lovers alike. Enjoy panoramic views from inside and out across over 22 wooded acres. Due to our proximity to hiking trails, lakes, rivers, breweries and wineries as well as Hunter Mountain (17 mi) and the towns of Catskill (26 mi) and Hudson (29 mi), this is an ideal location from which to explore the best of the Catskills, or to simply relax.

Guest favorite

Chalet in Tannersville

5 out of 5 average rating, 176 reviews

Catskill Chalet: Romantic Fall Escape w/Hot Tub

Camp Van Winkle is a place to relax, unwind & reclaim your sense of calm. Take time to connect with family and friends and discover the magic of the Legendary Catskills. In the summer, there's hiking, biking, boating & swimming. Winter brings skiing at Hunter & Windham, ice skating & cozy evenings by a warm fire. Take a soak in the Spa! Enjoy the quiet, the starry night sky & the fresh air all year round. Designed with love and care, we invite you to relax and stay awhile! Almost Home!!

Guest favorite

Chalet in Leeds

4.95 out of 5 average rating, 113 reviews

Catskill Chalet: Hot Tub, Fire Pit, Cozy, Private

**Steep driveway-highly suggest SUV** Step into the comfort of this stylish 3BR, 2.5 bath chalet, 2 hours from NYC. Nestled in tranquility, offering a perfect escape from the everyday hustle and bustle. It promises a secluded retreat with a rich amenity list, immersed in the dreamy natural ambiance, close to the town of Catskill, NY. ✔ 3 Comfy BRs ✔ Fully Equipped Kitchen ✔ Pool Table ✔ Front Deck (Electric BBQ) ✔ Hot Tub ✔ Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Parking See more below!

Guest favorite

Chalet in Wilmington

4.95 out of 5 average rating, 131 reviews

Mountain View Retreat: 5 Mi to MT Snow, Hot Tub

Come escape to Wilmington, Vermont. Stunning views of Mt. Snow, a small stream, and a large hot tub on 12 secluded acres. Only 10 minutes to Mount Snow and 30 minutes to Stratton our home is the perfect getaway for your VT adventure with all of your family and friends. Come ski, snowboard, snowmobile, hike, kayak, mountain bike, swim, or fish just minutes away! After your long day exploring come relax in the hot tub, by the fire, in the game room, or just out on our deck taking in the sunset!

Guest favorite

Chalet in Mount Tremper

4.98 out of 5 average rating, 103 reviews

Modern Mountain Chalet on 15 Acre Catskills Estate

This secluded "Frank Lloyd Wright" inspired home can be your own private mountain retreat and perfect haven for an escape from the city. Designed like a luxurious treehouse, the multi layers of porches and decks makes one feel as if they are sleeping in the clouds. The home offers rest and relaxation with the therapeutic effects of nature right at your doorstep and as a breathtaking backdrop. You'll be inspired by the beauty and peacefulness that awaits you from every corner of the home!

Guest favorite

Chalet in Jamaica

4.98 out of 5 average rating, 242 reviews

Vermont Chalet

Escape to our cozy A-frame on 3 private acres in Southern Vermont for a peaceful, secluded retreat. Relax to the soothing sounds of the river across the street while unwinding on the covered, enclosed porch. Enjoy a fully stocked kitchen, updated bathroom, strong WiFi, video games and books by a warm wood stove. Explore local towns, ski & board, or wander through our tranquil forest. With an EV charger, local artisan soaps, and warm woodstove, this is the perfect spot for a serene getaway.

Guest favorite

Chalet in Dover

4.92 out of 5 average rating, 288 reviews

A charming VT chalet

Charming chalet nestled in the Mt Snow valley. Relax to the sound of a babbling brook in the back yard while you hang around a stone fire pit! Unwind in the quiet serenity of this country home complete with fully equipped kitchen with a newly installed gas fireplace , a comfy open living room with flat screen cable tv & DVD player Roko & High speed Internet . We have a lock box located on the post near the front entrance. combo provided upon arrival . Washer & dryer located on first level.

Superhost

Chalet in Dover

4.86 out of 5 average rating, 233 reviews

The Mountain A-Frame at Mount Snow

Entire chalet-style A-Frame in Mount Snow with mountain views. Less than 1 mile from the base of Mount Snow and close to all the fun in the Green Mountains: AT access, swimming holes, covered bridges and more! Across the street you can hop on the Moover shuttle that takes you right to the mountain! 2 minute walk to market, coffee shop and local bar. 2 bedrooms + 1 loft, 1 bath, wrap around deck, cooking necessities, Smart TV and WiFi. You can find us on social (tag us!) @themountainaframe

Guest favorite

Chalet in Dover

4.94 out of 5 average rating, 104 reviews

8Min to MtSnow, HotTub, FirePit, GameRoom, Dogs Ok

✔ 8 Minutes to Mount Snow, 30min To Stratton, 60min to Okemo ✔ 4 Bedrooms, 3 Bathrooms, Sleeps 10 comfortably ✔ Hot Tub Under Pergola & String Lights ✔ String-Lit Fire Pit Area w/ Adirondack Charis ✔ Game Room With Air Hockey & Ring Toss ✔ Dog-Friendly ✔ Lake Whitingham/Harriman Reservoir is 20 minutes away to enjoy boating & fishing ✔ Fast Wifi For Remote Working & Streaming ✔ Quiet, Peaceful, & Private ✔ High Chair, Pack N' Play Provided ✔ All Linens/Towels/Soaps Provided

Guest favorite

Chalet in Stoddard

4.95 out of 5 average rating, 237 reviews

Highland Haus-70s AFrame-short walk to lake/canoe

Cozy 1975 A-frame chalet cabin sleeps 5 with a comfortable living space, two wood stoves, and a full kitchen. Located in the rural community of Stoddard. Enjoy the peace and quiet that this area has to offer. Many local hiking, swimming and fishing nearby. In warmer months, guests will have access to our canoe. It is less than a 2-hour drive from Boston to the Highland Haus! Winter Guests- please note that Shedd Hill rd is very hilly and all-wheel drive or 4-wheel drive is recommended.