Chalet holiday rentals in Berkshire County

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Top-rated chalet rentals in Berkshire County

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

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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, 437 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

4.96 out of 5 average rating, 75 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.

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

4.83 out of 5 average rating, 29 reviews

Cozy Winter Chalet I Close to Ski & Downtown Lenox

Your Modern Berkshires Winter 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. Perfect stylish Berkshires retreat for intergenerational families. Minutes to Lenox dining, Butternut & Bousquet skiing— games, ping pong and top-tier destinations minutes away. Healthy fam fun!

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

4.96 out of 5 average rating, 81 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. /\

An aerial view presents a modern open-plan home surrounded by lush greenery. The screened-in porch features seating, while a deck offers outdoor dining. A winding driveway leads up to the home, nestled within the tranquility of the mountainside. Ample nature surrounds the property.

Chalet in West Stockbridge

4.95 out of 5 average rating, 42 reviews

Secluded Mountain Home 7min from Great Barringtom

Sunlight filled, 3 Bed, 2.5 bath, modern, open-plan home in a quiet mountainside location, only 7 min from Great Barrington, 13 min to Lenox & Tanglewood. Cathedral ceilings, modernly furnished, well equipped kitchen with dining for 10. Enjoy mountain views with endless windows, screened porch and deck sitting with the trees. Fire pit for s'mores. Embrace the outdoors in any season - with apple picking, leaf peeping, skiing, sledding, spas, shopping, swimming, hiking etc., all 10 min drive.

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, 89 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 upgraded Internet with 2 internet satellite dishes, to handle Zoom calls & home work!

Guest favourite

Chalet in Otis

4.91 out of 5 average rating, 76 reviews

Thrill & Chill: Ski & Sauna in Winter Wonderland

Join our unique Berkshire vacation experience, away from the hustle and bustle: ❄️Minutes to ski (Otis Ridge), 20 min to Butternut ❄️Boost your wellness in the barrel sauna ❄️Relax around the gas fireplace ❄️Binge your fav show on the 80” TV ❄️Min. to restaurant & snow shoeing The newly designed light-filled interior offers comfort and style while being perfectly suited for children: 👉fully equipped kitchen (air-fryer, waffle maker, Nespresso) 👉home office (Fast Wifi) 👉arcade-style games

Top 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

5 out of 5 average rating, 15 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 offers unparalleled panoramic sunset views of the mountains and rights to Queechy Lake. On 7 private acres the Chalet offers the unique opportunity to disconnect from our busy lives and reconnect with ourselves, family, or friends. Imagine starting the day with sunrise yoga on the enormous mahogany deck and ending it with sunset cocktails on the same deck.

Superhost

An open-concept living area features high wooden ceilings and large windows that frame views of the Housatonic River. A wooden dining table accommodates several chairs, while comfortable seating is arranged around a coffee table. French doors lead to the outdoor deck, enhancing the space's connection to nature.

Chalet in Great Barrington

4.85 out of 5 average rating, 20 reviews

River Views, Screened Porch, Sun Deck, Fire Pit!

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!

A cozy cottage is nestled among lush greenery, featuring a wooden exterior with large windows. A balcony extends from the upper floor, furnished with several chairs. The surrounding landscape includes tall trees and a vibrant mix of plants, creating a serene natural environment.

Chalet in Stephentown

5 out of 5 average rating, 13 reviews

Ski Cottage in the Berkshire hills

Ten minutes from Jiminy Peak, but surrounded by woods. Perfect for a family ski getaway or a small group of friends, our cottage features a cathedral ceiling in the open living/dining area. There's a galley kitchen & a table for six. There are 3 bedrooms (two double, one twin), one full and one half bath. There's a washer dryer by the entryway and baseboard heating in every room. The nights are starry and tranquil, and the days reveal the beauty of the Berkshire mountains.

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, 55 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.

Top guest favourite

A spacious great room features high ceilings with wooden beams and large triangular windows. A wooden dining table is situated near the windows, while comfortable seating arrangements with neutral-toned upholstery are arranged around a central fireplace. Natural light fills the space, enhancing the open concept design.

Chalet in Richmond

4.97 out of 5 average rating, 98 reviews

Updated Berkshires Chalet Mins to Tanglewood/Lenox

Our place is 4 miles to Tanglewood, and very close to Berkshire Attractions, Skiing, Swimming / Boating, hiking, Summer Theater, Restaurants. Easy On/Off Mass Pike & Taconic Parkway. You’ll love our place because it's newly renovated, open concept two story great room - new kitchen with soapstone counters and SS appliances, screened porch for relaxing in the summer, central A/C, Beautiful secluded grounds. 7 person covered outdoor hot tub; Water Filtration System.