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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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, 457 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, 79 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

Chalet in Averill Park

4.94 out of 5 average rating, 93 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. /\

A private in-ground pool is set among tree-covered surroundings, showcasing a tranquil blue water surface. Four lounge chairs line the pool deck, providing a relaxing space for guests. Lush greenery is present in the background, enhancing the secluded atmosphere.

Chalet in East Chatham

4.85 out of 5 average rating, 27 reviews

Berkshires Vacation Home 6BR, 4 ski mtns, hot tub

A getaway at the edge of the Berkshires - family friendly, 4 ski mountains nearby, hot tub, charming towns, fireplace, expansive deck, sunset views, private in-ground pool, BBQ, secluded, wooded, nearby lakes, hiking, Tanglewood for summer music and performance festivals. We've set up this vacation home for ourselves to enjoy, so you know we've put our hearts into it and are excited for you to create memories for a lifetime. The home is set up beautifully for families and groups of friends.

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

4.86 out of 5 average rating, 37 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!

Top guest favourite

A charming chalet is framed by lush greenery, featuring a stone pathway leading to a welcoming front porch. The house, designed with a slanted roof, has a balcony with a white railing above the entrance, enhancing its rustic appeal.

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

Guest favourite

Chalet in Otis

4.9 out of 5 average rating, 84 reviews

Spring skiing with friends & family - Berkshires

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

Superhost

Chalet in Great Barrington

4.86 out of 5 average rating, 21 reviews

Post & Beam: River Views, Screened Porch, Sleeps 7

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 spacious living room features a striking stone fireplace, complemented by stylish woven light fixtures overhead. Comfortable seating arrangements include a soft, textured area rug and a round table adorned with floral decor, surrounded by cozy poufs and natural light illuminating the space.

Chalet in Monterey

4.92 out of 5 average rating, 13 reviews

Butternut Ski Chalet on Lake w/HotTub Sauna by GB

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.

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 & Sk

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

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

4.89 out of 5 average rating, 19 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.