Chalet vacation rentals in Berkshire County

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Berkshire County

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Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 379 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

Chalet in Great Barrington

4.95 out of 5 average rating, 64 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 favorite

Chalet in Averill Park

4.95 out of 5 average rating, 61 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. /\

Chalet in Hillsdale

4.9 out of 5 average rating, 62 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!

Superhost

Chalet in Lenox

4.78 out of 5 average rating, 18 reviews

Peaceful Berkshire Chalet, Walk to Lenox

Family friendly, spacious cabin. Tons of natural light a wood stove and private garden. Woodsy feeling in contemporary setting next to Kennedy Park. Downstairs is mobility friendly w/ 1 twin ensuite, 1 Queen w/ separate full bath & TV room. Upstairs: Main bedroom with w/separate full bath and sitting area. Lovely deck, stunning views. Ping pong table and plenty of games for kids! 10 mins drive to Tanglewood, Kripalu; 8 min drive to Bousquet Ski Mtn., 15 to Red Lion & 25 to Butternut Mtn.

Guest favorite

Chalet in Monterey

4.98 out of 5 average rating, 80 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 favorite

Chalet in Otis

4.9 out of 5 average rating, 52 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

Guest favorite

Chalet in Canaan

5 out of 5 average rating, 11 reviews

SRC-Hudson Valley/Berkshires Cultural Corridor

We welcome you to explore the magic of Sunset Ridge Chalet (aka SRC). Ideally situated within the Hudson Valley/Berkshires cultural corridor, SRC offers unparalleled panoramic sunset views of the mountains. Sitting on 7 private acres the Chalet offers our guests the unique opportunity to disconnect from their busy lives and reconnect with themselves, family, or friends. Imagine starting the day with sunrise yoga on the mahogany deck and ending it with sunset cocktails on the same deck.

Guest favorite

Chalet in East Chatham

5 out of 5 average rating, 19 reviews

Dream getaway - mtn views, pool, deck, fire pit

A getaway with everything you dream of - expansive deck, BBQ, sunset views, private in-ground pool, secluded, wooded, nearby lake (9 mins), hiking nearby, 4 Ski mountains a short drive away, quaint towns, 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 or groups of friends.

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 favorite

Chalet in Richmond

4.97 out of 5 average rating, 93 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.

Guest favorite

Chalet in New Marlborough

4.92 out of 5 average rating, 53 reviews

Modern & Secluded on 40 Acres - Fast Wi-fi

Total privacy and beautiful mountain views, set on 40 acres, floor-to-ceiling windows, wrap-around deck with table, and chairs. You can't see any other houses and they can't see you. 20ish min to Butternut and Catamount Ski 10-15 min to Restaurants and Shops Great outdoor space. 2 large TVs with Direct TV, Netflix, Amazon. Wifi throughout. Whirlpool bath. On-property hiking trails. ***VIDEO (copy and paste) https://rb.gy/29we4t***