Chalet holiday rentals in Berkshire County

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Berkshire County

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

%{current} / %{total}1 / 1

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, 463 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

Top 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

4.96 out of 5 average rating, 80 reviews

Berkshire "Zen" Cottage

"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.

Top guest favourite

A mid-century A-frame house is set within a lush landscape, surrounded by trees displaying autumn colors. A spacious driveway leads to the entrance, and a large deck with railings extends along the front, offering an inviting outdoor space.

Chalet in Averill Park

4.93 out of 5 average rating, 92 reviews

A Hidden Sparrow

/\ Keeping it cozy, yet modern. Our take on hygge minimalism. A Hidden Sparrow is a classic mid-century A-frame nestled on 60+ acres for hiking and has a picturesque creek that flows in the front of the property. With fresh upgrades, tasteful aesthetic and comfy accommodations, A Hidden Sparrow is an idyllic sanctuary offering complete privacy for your next getaway. This all season escape is the perfect place to disconnect from your typical dwelling and enjoy everything nature has to offer. /\

The exterior of a charming house is displayed, featuring a steep, gabled roof and multiple levels. A spacious deck with white railings spans the front, adorned with hanging plants. Surrounding greenery includes colorful autumn foliage and a landscaped yard with patches of flowers.

Chalet in Hillsdale

4.86 out of 5 average rating, 65 reviews

Natural Splendor: Forest Luxury Retreat

Discover your perfect retreat near the heart of the Berkshires! This charming house offers tranquility year-round. In autumn, vibrant golds surround you; in winter, enjoy the warm fireplace while snow dances outside. The game room features pool and ping pong tables, and the spacious family room has surround sound and a 65" TV. Relax on the screened porch or large decks, gather around the fire pit, and enjoy a baby grand piano. Close to top attractions and restaurants, your ideal getaway awaits!

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, 40 reviews

Cozy Winter Chalet I Close to Ski & Downtown Lenox

Your Modern Berkshires Ski Escape Elegant, light-filled chalet beside Kennedy Park. Sleek design meets comfort with a mesmerizing view, spacious living room, and a serene garden. Main suite upstairs with bath and comfy sitting area; downstairs features a queen room, twin ensuite, and cozy TV lounge. Stylish winter Berkshires retreat for intergenerational families. Minutes to Lenox dining, Butternut & Bousquet skiing— snow-shoeing, ping pong and top-tier destinations minutes away. Healthy fun!

Guest favourite

Two white Adirondack chairs are positioned on a grassy slope, facing a vibrant sunset over distant mountain silhouettes. The warm hues of the setting sun create a serene backdrop, with trees framing the scene and a peaceful atmosphere enveloping the area.

Chalet in Canaan

4.88 out of 5 average rating, 17 reviews

SRC-Hudson Valley/Berkshires Cultural Corridor

We welcome you to explore the magic of Sunset Ridge Chalet (SRC). Ideally situated in the Hudson Valley/Berkshires cultural corridor, SRC is a custom-designed mountain retreat that balances dramatic open-concept architecture with the cozy warmth of a family home. The Chalet offers unparalleled panoramic sunset views of the mountains and rights to Queechy Lake. 7 private acres offers the unique opportunity to disconnect from our busy lives and reconnect with ourselves, family, or friends.

Superhost

The open living area features wood-paneled walls and a high ceiling, with ample natural light streaming through large windows. A green sectional sofa and a leather armchair are positioned over a geometric area rug, with a dining area visible in the background.

Chalet in Great Barrington

4.86 out of 5 average rating, 21 reviews

Low Spring Rates: Wood stove & screened porch!

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

A modern living room features a large, plush sectional sofa adorned with soft white throws. Natural light floods in through expansive windows, showcasing a beautiful view of the lake. A stone fireplace adds charm, while a television is mounted above, providing entertainment.

Chalet in Monterey

4.92 out of 5 average rating, 13 reviews

Sleek Butternut Ski Chalet Lakefront HotTub Sauna

Newly Renovated Berkshires chalet with HOT TUB & Sauna, Pet friendly, 5BR 4 full bath on Lake Garfield 5 min to Ski Butternut, 15 min to Ski Catamount, 15 min Great Barrington dining /shops. Spacious, family-friendly home sleeps 14 with 2 living rooms, out door hot tub for 6, indoor infrared sauna, wood fireplace, BBQ, Solo fire pit sitting 6, fenced yard, decks, and 2 kayaks. Short walk to lake beach. Perfect for ski trips, lake stays, and group and family getaways.

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, 91 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.

Chalet in West Stockbridge

4.95 out of 5 average rating, 44 reviews

Modern Mtn Chalet | 7m to Great Barrington & Ski

Modern mountain retreat with cathedral ceilings & forest views. Perfectly located for après-ski dinners for 10 or simply curling up by the fireplace. Enjoy a secluded mountainside setting just 7 mins to Great Barrington & Butternut Skiing, and 15m to Catamount or Lenox. • Luxury Kitchen: Open-plan & fully equipped • Outdoors: Screened porch, deck & fire pit • Adventure: Near spas, hiking, shopping & Tanglewood • Winter: 4WD/AWD recommended

Chalet in East Chatham

5 out of 5 average rating, 8 reviews

East Chatham Spacious 5BR House Pool Sauna AC

Skiing nearby! 5BR retreat with sauna — perfect for large family or friends gatherings. Cook, connect, and unwind in rustic modern luxury. Nestled between the Hudson Valley and the Berkshires, this curated 5-bedroom estate features cathedral ceilings, panoramic forest views and a private sauna. Designed for rest and reconnection, with fast Wi-Fi and big-screen smart TVs for cozy holiday evenings. 20 min away from Jiminy Peak - skiing.