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.

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Chalet in West Stockbridge

4.96 out of 5 average rating, 46 reviews

Modern Mtn Chalet | Great Barrington & Tanglewood

Modern 3-BR Mountain Retreat. Sunlight-filled home (dining for 12) with cathedral ceilings in a secluded setting. Summer-ready: Large deck, screened porch, grill, firepit. 10 mins to Great Barrington/Stockbridge. Enjoy Tanglewood (20m), Norman Rockwell Museum (10m), Appalachian Trail hiking, and nearby lake swimming. • Luxury Kitchen: Open-plan & fully equipped • Outdoors: Screened porch, deck & fire pit • Culture: Near to galleries, antiques, historic homes, great dining, & farmer's markets.

Top guest favourite

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, 475 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 favourite

A spacious living area features large windows that provide ample natural light and views of the surrounding greenery. A cozy seating arrangement with patterned cushions is complemented by a stone fireplace and a rustic wooden shelf. A round coffee table is centered on a decorative area rug.

Chalet in Great Barrington

4.95 out of 5 average rating, 83 reviews

Berkshire "ZEN" Chalet

"ZEN" Palace Chalet perfect spot to chill & relax after a day of exploring or skiing. SPACIOUS,secluded,quiet, great grounds -3 bdrm 2 ba with LUSH VIEWS endless windows. BEAUTIFUL exposed wood beams & ceilings throughout. Super family friendly. 5 min GREAT BARRINGTON, Butternut, Catamount, great food, nature trails, lakes, great shopping & farmer's markets. Close to STOCKBRIDGE,Tanglewood, Norman Rockwell Museum, Wheatleigh, Kirpalu,Canyon Ranch & HUDSON NY. Accessible knowledgable local host.

Guest favourite

Chalet in Charlemont

4.91 out of 5 average rating, 22 reviews

Joia Verde| Dog-Friendly Mtn Cabin| Trails| MTB

Joia Verde Mtn Retreat, a private 120+ acre Berkshire retreat surrounded by forest, trails, and a serene pond. This secluded hideaway offers true peace, quiet, and space to reconnect with nature. Highlights: • Fire pit & outdoor seating • Natural swim pond (seasonal) • 120+ acres of private trails • Dog-friendly • Starry skies, total quiet, complete privacy • Second house available for larger groups • Local attractions: skiing, kayaking, white water rafting, zip-lining, and mtn biking

Guest favourite

A wooden deck extends from the back of the house, overlooking a fire pit surrounded by several adirondack chairs. Vibrant fall foliage complements the tranquil setting, with a winding path leading to the house, where large windows invite natural light.

Chalet in Charlemont

4.97 out of 5 average rating, 146 reviews

Ski, Raft & Relax | Lodge w/ Pool Table & Fire Pit

On your journey to The Lodge on Warner Hill, you will pass through a nostalgic covered bridge, drive by a babbling brook, and meander up a winding 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 10 minutes from Berkshire East and the Deerfield River

Superhost

Chalet in Great Barrington

4.86 out of 5 average rating, 22 reviews

Sunset River Views, SIP, Spotless, Sleeps 8

Conway House: Conway House: Brand New Contemporary Chalet with 3 Bedrooms, 2.5 baths and sparkling river views! Sleeps 6 (8 max). Screened porch, central AC, propane wood stove, 2 HDTVs, 2 car garage with direct entry, propane grill, outdoor seating with solo wood stove, high speed internet, good cell service, washer/dryer, whole-house water filter for clean drinkable water, decks with river views and plenty of outdoor seating! All linens included. Pets considered. No Smoking, please!

Guest favourite

The cabin is nestled in a wooded area, surrounded by lush greenery. A large deck extends from the front of the home, with firewood stacked neatly beside it. The architecture features an A-frame design, blending harmoniously with the natural landscape.

Chalet in Lenox

4.88 out of 5 average rating, 43 reviews

Modern Chalet Near Tanglewood & Downtown Lenox

Your Modern Berkshires Escape Light-filled modern chalet next to Kennedy Park with beautiful views, a spacious living room, and a peaceful garden for morning coffee, evening wine or yoga. Designed for families and friends, with a private upstairs main suite plus comfortable guest rooms. Minutes to Tanglewood, downtown Lenox, hiking trails, lakes, great dining, and the best of the Berkshires. Perfect for a summer getaway filled with music, nature, and time to unwind. Healthy fun!

Top guest favourite

Chalet in Otis

4.92 out of 5 average rating, 98 reviews

Family Lake Retreat | Sauna, Deck & Games

🚣 Kayak, swim, or float on the lake 🧖‍♂️ Relax in the Scandinavian barrel sauna 🍕 Grill, bake in the pizza oven, or gather around the firepit 🎶 Enjoy restaurants and Tanglewood (20 min) All Year Round: The light-filled interior offers comfort and style: 📺 Two large flat-screen TV (75" in Master bedroom, 80" in living room) 🍳 Fully equipped kitchen (air-fryer, waffle maker, Nespresso) 💻 Home office with fast WiFi 🎮 board games and outdoor arcade-style games and more

Top guest favourite

A cozy living room features two light-colored sofas adorned with decorative pillows. A wooden coffee table sits at the center, complemented by a woven area rug. A tall bookshelf filled with baskets is visible in the background, alongside a small side table and wall art.

Chalet in Monterey

4.98 out of 5 average rating, 95 reviews

Cozy French Country Chalet

Perfectly situated, this cozy French Country chalet is minutes to downtown Monterey, Lake Garfield & just 10 minutes to Butternut for skiing. Family friendly, this home is stocked with games, movies & books for a fun-filled trip. If you're looking for a relaxing Berkshires getaway, look no further than this well-cared-for home, stocked with amenities to make your trip comfortable & relaxing! The home also has high-speed broadband internet, capable of streaming & more!

Guest favourite

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

4.93 out of 5 average rating, 58 reviews

Modern Secluded Ski Chalet | 40 Acres | Family

Enjoy privacy at a cozy mountain home on 40 acres, minutes from ski resorts and shops. Floor-to-ceiling windows offer stunning views. This pet-free retreat is ideal for families seeking adventure & relaxation. Kids enjoy the playroom and outdoor space while parents relax in the jacuzzi tub or comfy living area. The fully stocked kitchen makes meal prep simple. Friendly local hosts provide restaurant tips, babysitter bookings and insider advice to enhance your stay.

Guest favourite

The open-plan living space features a wood-burning stove surrounded by comfortable seating. Expansive windows allow natural light to fill the room, showcasing the wooden interiors. A dining area with a table and chairs is visible, along with a cozy atmosphere enhanced by the surrounding greenery.

Chalet in Otis

4.91 out of 5 average rating, 22 reviews

Berkshires Chalet Natural Setting Deck & Fire Pit!

Relax with the whole family at this peaceful 4 bedroom 3 bath chalet as your base to enjoy the great outdoors of the Berkshires. Close to lakes, hiking trails and just a short drive to Tanglewood and Jacob's Pillow. In winter Ski Otis Ridge a mile away, or a 25 minute drive to Butternut. Relax and enjoy family time in the open plan living space with wood burning stove and deck, or venture down to the firepit in the large secluded yard.

Top guest favourite

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, 35 reviews

Spectacular Lakefront Chalet – Beach, AC, 3BR

Relax at a beautiful LAKEFRONT CHALET set on a peaceful 3-acre peninsula in Orange, Massachusetts. Enjoy sweeping water views, expansive grounds, and a sandy beach with a floating dock. Swim, canoe, fish, or explore nearby state forests and hiking trails. In the evening, unwind by the lakeside fire pit. The property features unique Greek statues and beautifully landscaped scenery, creating a memorable and serene lakeside retreat.