Chalet vacation rentals in Western Massachusetts

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Western Massachusetts

Guests agree: these chalets are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

The entryway features a welcoming entrance with a wooden door, adorned with a green wreath. A glimpse into the bright interior reveals modern seating and natural light streaming through large windows, enhancing the inviting space that awaits inside.

Chalet in Wilmington

4.97 out of 5 average rating, 115 reviews

Snug Chalet - Wi-Fi + Close to Mount Snow

This stylish 1971 chalet is a country retreat with modern comforts for you and your family... complete with strong WiFi and a fenced-in dog yard! The minimal cabin is tucked in the trees and set up for families and friends, pet & kid-friendly. 10-15 Minutes to Mount Snow 10-15 Minutes to Downtown Wilmington This is a country house, not a boutique hotel :) If booking during winter or spring months, we HIGHLY recommend a 4wd vehicle as the weather can cause some tough road conditions (snow/mud).

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, 432 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

A chalet-style home is surrounded by lush greenery, featuring a large three-sided wrap-around deck. Tall windows dominate the front, allowing ample natural light. To the side, a wooden garage complements the main structure, set against a backdrop of trees and an expansive lawn.

Chalet in Stamford

4.93 out of 5 average rating, 108 reviews

Peaceful VT Chalet w/ Mountain View’s

My peaceful 3-bedroom chalet has everything you need for your VT trip. The house comes with a washer, dryer, Roku TV’s, pullout queen couch. 2.5 bathrooms, indoor elec. fireplace, outdoor fire pit and fully equipped kitchen.Short driving distance to several popular golf courses, shops, restaurants, breweries, fishing, white water rafting, hiking, kayaking, ATV/snowmobile trails, & mountain slopes. An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

Guest favorite

A wooden deck overlooks a serene lake, featuring a round glass table with a central umbrella. A charcoal grill is positioned nearby, surrounded by trees that enhance the natural setting.

Chalet in Winchester

4.85 out of 5 average rating, 134 reviews

Chalet Sonsie: A Sweetwater Stay

Chalet Sonsie is a freshly-renovated waterfront getaway, where you can enjoy breathtaking views of Forest Lake year-round, from every room and all 3 levels of decks! Whether you're traveling with the kids, friends, or just looking for a quiet fishing retreat, there's something here for everyone. This cozy 2-bedroom home features 2 full kitchens, 1.5 baths, expansive fireplace and TV, plus a game room complete with foosball and mini-arcade! Book today, or check out other Sweetwater Stays! -Patti

Top guest favorite

The log-built chalet is surrounded by lush greenery and rolling hills. A spacious porch wraps around the house, and a fire pit with seating is visible in the foreground, providing a welcoming outdoor space amidst the natural landscape.

Chalet in Gilboa

4.98 out of 5 average rating, 168 reviews

Secluded Chalet w/ Unforgettable Views on 22 Acres

A nature-lover's oasis, this 3-bedroom/4-bed/2-bath log-built chalet with contemporary furnishings is perched high along the northernmost edge of the Catskill Mountains offering unforgettable panoramic views from inside and out across 22+ secluded acres. Due to its proximity to hiking trails, lakes, rivers, breweries and wineries as well as Windam (7 mi), Hunter (16 mi), Catskill (26 mi) and Hudson (29 mi), this is the ideal location from which to explore the best the Catskills has to offer.

Top guest favorite

A charming lodge is nestled within a wooded landscape, showcasing a vast back deck with seating and a central fire pit surrounded by comfortable chairs. Colorful autumn leaves frame the scene, highlighting the welcoming atmosphere of the outdoor space.

Chalet in Charlemont

4.99 out of 5 average rating, 118 reviews

The Lodge on Warner Hill

On your journey to our lodge, you will pass through a nostalgic covered bridge, drive by a babbling brook, and meander up a winding dead-end dirt road. Our home sits in a quiet, peaceful 5-acre setting. It has been completely remodeled with earth-tone charm. Enjoy your time with friends and family relaxing, reading a book, playing pool, barbequing on the back deck, gazing at the stars, or hanging out by the fire pit. Located less than 10 minutes from Berkshire East and the Deerfield River

Top guest favorite

An open living area features a high wooden ceiling and large windows, allowing natural light to fill the space. A cozy seating arrangement is complemented by a sculptural centerpiece on a long table, with a fireplace set against a dark brick wall. Two armchairs add to the inviting atmosphere.

Chalet in Winhall

4.98 out of 5 average rating, 110 reviews

Mountain view chalet with hot tub & fire pit!

Welcome to the Vermont View Chalet! This spacious, family-friendly property is perfect for year-round enjoyment. With the mountain view as your backdrop, come unplug by the fire pit and unwind in the hot tub. Perfectly situated between Manchester (shopping & dining) and Bromley/Stratton (skiing and entertainment). You're also just 2 minutes away from the Appalachian trail for the best hiking and fall foliage Southern Vermont has to offer. Look no further, you've arrived at your destination.

Top guest favorite

A cozy log cabin is nestled among tall trees, with sunlight filtering through the leaves. The surrounding ground is covered in vibrant autumn leaves, and a winding path leads to the front entrance of the home, offering a serene and inviting atmosphere.

Chalet in Londonderry

4.94 out of 5 average rating, 121 reviews

10 min from Stratton! Log Cabin w/ Beautiful Views

Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!

Guest favorite

The A-Frame chalet is set amidst vibrant autumn foliage, showcasing a wrap-around deck with wooden railings. A balcony extends above, offering a view of the surrounding trees and an inviting outdoor space with seating.

Chalet in Dover

4.87 out of 5 average rating, 268 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

Top guest favorite

The chalet is set against a backdrop of mountains and trees. The property features a large green lawn, and two dogs are seen resting on the grass in the foreground. The warm exterior of the home, complete with a deck, can be seen in the background.

Chalet in Wells

4.98 out of 5 average rating, 103 reviews

Chalet on a Hill w/ Mountain & Lake View, Hot Tub

A beautiful chalet situated between mountains and Lake St Catherine. Whether on the deck or inside the house, you can enjoy the tranquil and serene view of the mountains and the lakes. At over 3000 sq ft, the house offers multiple gathering areas, including separate living room(s), a sociable kitchen, a pool table, and a bar. A perfect home for a retreat. Located less than 10 mins from Lake St Catherine Park and country club and many hiking and mt-biking options for the active guests.

Guest favorite

Chalet in Dover

4.97 out of 5 average rating, 130 reviews

Private Brook Chalet: Hot Tub - Fire pit - Ski

The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best food VT has to offer.

Superhost

An A-frame chalet is illuminated at dusk, showcasing its triangular structure and charming front porch. Warm light spills from the windows, and twinkling string lights enhance the serene outdoor setting surrounded by trees.

Chalet in Stoddard

4.95 out of 5 average rating, 279 reviews

Highland Haus AFrame Lake Access Vintage 70s Charm

Authentic 1975 A-frame chalet nestled in peaceful Stoddard countryside. This cozy cabin sleeps 5 with two wood stoves and full kitchen. Perfect rural retreat just 2 hours from Boston! Explore nearby hiking trails, swimming spots, and fishing areas. Summer bonus: complimentary canoe access! Highland Haus offers a tranquil escape with vintage charm. Note for winter visitors: Shedd Hill Road requires AWD/4WD due to steep terrain. Your cozy retro hideaway awaits!