Chalet vacation rentals in The Berkshires

Find and book unique chalets on Airbnb

Top-rated chalet rentals in The Berkshires

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Chalet in Grahamsville

4.96 out of 5 average rating, 157 reviews

Chalet in the mountains with a breathtaking view!

Come and enjoy our Catskills mountain view chalet. Escape the chaos of the city for peace and serenity. In our home you'll find an open concept kitchen/dining and living room space, a huge deck, 2 bedrooms, a newly renovated bathroom and a loft work space. Take in the country skyline view with a glass of wine on the deck while listening to meditative sounds of the babbling brook. Don't forget to bring groceries as the best way to enjoy the chalet is with a home cooked meal with those you love

Guest favorite

Chalet in Stratton

4.97 out of 5 average rating, 104 reviews

Stratton/MtSnow HotTub, Sauna, Treehouse, Firepit

HYGGE HOUSE is your private luxury escape on 4 acres of wooded bliss. Perfect for families and small groups of nature-loving adults to make memories in all that the Green Mountains have to offer in any season; hike, mountain bike, kayak, fish, ski, snowshoe, paddle, & golf. Relax in your private HOT TUB and SAUNA. Hang out amongst the trees atop the TREEHOUSE. Take a nap in the HAMMOCK. Roast marshmallows by the FIRE PIT. Located 8 min to Mt Snow & 12 to Stratton Mountain. NO SMOKERS OF ANY KIND

Guest favorite

Chalet in Otis

4.95 out of 5 average rating, 372 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 Tannersville

5 out of 5 average rating, 169 reviews

Catskill Chalet: Romantic Fall Escape w/Hot Tub

Camp Van Winkle is a place to relax, unwind & reclaim your sense of calm. Take time to connect with family and friends and discover the magic of the Legendary Catskills. In the summer, there's hiking, biking, boating & swimming. Winter brings skiing at Hunter & Windham, ice skating & cozy evenings by a warm fire. Take a soak in the Spa! Enjoy the quiet, the starry night sky & the fresh air all year round. Designed with love and care, we invite you to relax and stay awhile! Almost Home!!

Guest favorite

Chalet in Leeds

4.94 out of 5 average rating, 109 reviews

Catskill Chalet: Hot Tub, Fire Pit, Cozy, Private

**Steep driveway-highly suggest SUV** Step into the comfort of this stylish 3BR, 2.5 bath chalet, 2 hours from NYC. Nestled in tranquility, offering a perfect escape from the everyday hustle and bustle. It promises a secluded retreat with a rich amenity list, immersed in the dreamy natural ambiance, close to the town of Catskill, NY. ✔ 3 Comfy BRs ✔ Fully Equipped Kitchen ✔ Pool Table ✔ Front Deck (Electric BBQ) ✔ Hot Tub ✔ Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Parking See more below!

Guest favorite

Chalet in Napanoch

4.95 out of 5 average rating, 216 reviews

Catskills Aframe, Water View, Goat Sanctuary

This charming Aframe is tucked into the Catskill mountains, with spectacular seasonal views of the Rondout Reservoir. This house has a cozy feel with rustic charm and is the perfect getaway for those wishing to escape to nature. Outdoor enthusiasts will enjoy numerous local hiking trails and we're just 25 minutes from popular areas such as Mohonk Preserve, Sams Point, Minnewaska. A goat sanctuary, animal lovers can visit with our 29 recsue goats, chickens, dogs and of course, local wildlife!

Guest favorite

Chalet in Mount Tremper

4.98 out of 5 average rating, 100 reviews

Modern Mountain Chalet on 15 Acre Catskills Estate

This secluded "Frank Lloyd Wright" inspired home can be your own private mountain retreat and perfect haven for an escape from the city. Designed like a luxurious treehouse, the multi layers of porches and decks makes one feel as if they are sleeping in the clouds. The home offers rest and relaxation with the therapeutic effects of nature right at your doorstep and as a breathtaking backdrop. You'll be inspired by the beauty and peacefulness that awaits you from every corner of the home!

Guest favorite

Chalet in Gilboa

4.98 out of 5 average rating, 126 reviews

Luxurious Chalet w/ Incredible Views on 22 Acres

A skier’s and nature lover's paradise located just seven miles from Windham! This 3-bedroom/4-bed/2-bath chalet is perched high along the northern edge of the Catskill Mountains offering panoramic views from inside and out across its 22 wooded acres. Due to its proximity to hiking trails, lakes, rivers, breweries and wineries as well as Hunter Mountain (17 mi) and the towns of Catskill (26 mi) and Hudson (29 mi), this is an ideal location from which to explore the best of the Catskills.

Guest favorite

Chalet in Maplecrest

4.97 out of 5 average rating, 234 reviews

Windham Chalet w BBQ Hut, Pizza Oven and Hot tub

Escape to a peaceful retreat just five minutes from Windham! Our private cabin offers relaxation and comfort, featuring a spacious deck with a hot tub, swing bed, gas grill, and bar seating. Enjoy the unique charm of our Scandinavian BBQ hut, perfect for year-round grilling and cozy gatherings. Whether rain or shine, you can soak in the beauty of nature, grill, or gather around the fire pit under the covered deck. Offering an escape for nature lovers seeking tranquility and comfort!

Guest favorite

Chalet in Tannersville

4.94 out of 5 average rating, 230 reviews

Romantic Chalet~ Hot Tub ~ Near Hunter Mountain

The Catskills Hideaway is a place to step back in time, unwind with a cocktail by the fire, soak in the hot tub, read a book in one of the hanging chairs, toast marshmallows with friends, prepare a special meal in the kitchen, ski your heart out, hike one of the many local trails, visit the falls, enjoy the local restaurants- whatever you’re dreaming about for your Catskill escape- this is THE PLACE! Hunter Mountain 4.8 miles Windham Mountain 12.6 miles Kaaterskill Falls 4 miles

Guest favorite

Chalet in Hurley

4.98 out of 5 average rating, 208 reviews

Exquisite Chalet near to Woodstock's best scenery

Newly renovated 3 bedrooms, 2 baths chalet for 6, one mile from stunning Ashokan reservoir view, on private lane but in the heart of Catskills, 10 min from Woodstock, Kingston and exit 19 off hwy 87, with fireplace, wraparound deck, deer-proof yard, firepit, barbecue, veggie garden. Ideal for couples, families, friends. Minutes to ski, ice climbing, iceskating, swimming, hiking, rock climbing, tubing, fishing, scenic walks, biking trails, food markets & excellent restaurants.

Guest favorite

Chalet in Fleischmanns

4.99 out of 5 average rating, 191 reviews

Crows Nest Mtn. Chalet

Elevated into the Mountainside, Crow’s Nest looks out onto a spectacular view of the Catskill Mountain range of Belleayre. Grab a cup of coffee and watch the sunrise from the back deck or bask in the glow of the sunset while relaxing in the hot tub or hammock. This is an incredible place to unwind and take in that fresh mountain air or retreat to one of the many hangout spots in this newly renovated home. Follow us on IG : @crows_nest_catskills