Chalet vacation rentals in Western Massachusetts

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Western Massachusetts

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Guest favorite

Chalet in Cragsmoor

5.0 out of 5 average rating, 226 reviews

Scandinavian-Style Chalet with Scenic Views

Wake up to hilly views from this Scandinavian-inspired chalet boasting wood-paneled cathedral ceilings, sharp furnishings, and concrete floors. Share a glass of wine with a friend beside a sleek fireplace and live-edge coffee table in a chic living area. Please inform the host if you plan to bring a dog as there is a 20 pound weight limit. Maximum number of guests/visitors/people permitted on the property is 2. Our current housekeeping policy since Covid-19 is we block our calendar a minimum of two days after each guest checks-out for cleaning and disinfecting. Polished concrete floors with radiant heat, 8 ft. tall windows, 10 ft. walls, wood vaulted ceiling, air conditioning, gas fireplace fully equipped kitchen (oven, stove, refrigerator, dish washer, coffee maker, microwave, toaster, ninja) washer and dryer. Full bathroom with tile and marble. Free Wi-Fi, 50" smart tv The chalet is a free standing private building with a deck and covered porch. It has it's own barbecue, hammock and fire pit for your private use. Guests have full access to the owners 20 acre property which includes some short trails through the woods and an outdoor shower. The owner lives on the property in a seperate residence and is available for any assistance guests require. The chalet is set in an area of seclusion on the Shawangunk Mountains in Cragsmoor. A short drive away is the entrance to Sam's Point Preserve with miles of hiking trails and incredible scenic views. Effective 5/1/22 a reservation is required to enter Sam’s Point on the weekend. Go to ReserveAmerica. com to make a reservation. Minnewaska State Park and Mohonk Preserve are nearby. Dining and shopping are within a five to ten minute drive. There is no public transportation nearby so the only way to get to us is by motor vehicle. If your coming up during the winter season a four wheel drive vehicle is highly recommended. The owner has two cats that live on the property. The cats are never permitted inside the chalet.

Feb 22 – Mar 1

$368 per night

Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 350 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

Dec 10 – 17

$327 per night

Guest favorite

Chalet in Dover

4.95 out of 5 average rating, 100 reviews

Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow

My super cozy mountain chalet 10 mins from Mount Snow is the perfect spot to host your Vermont vacation! Let the grownups cozy up by the wood-burning fireplace in the living room, while the kids hang out in the second living room and game room downstairs. With air hockey, shuffleboard, and poker table, they’ll be busy for hours. Hmmm….maybe the grownups will claim that space for themselves! After a long day on the slopes or trails, the sauna, hot tub, or jacuzzi tub will feel great on tired musc

Aug 2 – 9

$464 per night

Guest favorite

Chalet in Cummington

4.86 out of 5 average rating, 101 reviews

Berkshire A-Frame Chalet!

Our secluded home is just off of route 9 in Cummington. We are less than 1 hour away from many attractions including Tanglewood, Mass MoCA, Glendale Falls and Northampton. This area is not only beautiful for hiking, but also motorcycle riding here is exquisite! No wifi or cable (plenty of movies!), good cell phone coverage for Verizon and AT&T (tMobile has not worked in the past, but recently guests have said that it does work). Friendly pets welcome! 1 pet maximum. We abut Shire Village Camp.

Jul 6 – 13

$150 per night

Guest favorite

Chalet in Northville

4.99 out of 5 average rating, 141 reviews

Stunning 3-Unit Lakefront! Hot Tub & Private Dock

Welcome to WINDOWS ON THE WATER - your Great Sacandaga Lake Waterfront Retreat! HOT TUB * FIREPIT * PRIVATE DOCK THREE Interconnected Units on 1-acre wooded lot. Perfect for Extended Families & Larger Groups.Sip your morning coffee on the Deck before launching Kayaks from your own dedicated Dock- NO road to cross to reach the lake! Soak in the 7-person spa overlooking the water... Enjoy all that this lake offers -just 30 min from world-renowned Saratoga Springs (spas*racetrack*shopping*dining

Feb 2 – 9

$941 per night

Guest favorite

Chalet in Gilboa

4.97 out of 5 average rating, 103 reviews

Luxurious Chalet w/ Panoramic Views on 22+ Acres

A nature-lover's paradise, this 3-bedroom/4-bed/2-bath log-built chalet with contemporary furnishings is perched high along the northernmost edge of the Catskill Mountains offering unforgettable panoramic views from inside and out across 22+ secluded acres. Due to its proximity to hiking trails, lakes, rivers, breweries and wineries as well as Windam (7 mi), Hunter (17 mi), Catskill (26 mi) and downtown Hudson (29 mi), this is an ideal location from which to explore the best of the Catskills.

Jun 18 – 25

$352 per night

Guest favorite

Chalet in Napanoch

4.95 out of 5 average rating, 206 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!

Jan 3 – 10

$149 per night

Guest favorite

Chalet in Dover

4.93 out of 5 average rating, 265 reviews

A charming VT chalet

Charming chalet nestled in the Mt Snow valley. Relax to the sound of a babbling brook in the back yard while you hang around a stone fire pit! Unwind in the quiet serenity of this country home complete with fully equipped kitchen with a newly installed gas fireplace , a comfy open living room with flat screen cable tv & DVD player Roko & High speed Internet . We have a lock box located on the post near the front entrance. combo provided upon arrival . Washer & dryer located on first level.

Dec 4 – 11

$134 per night

Superhost

Chalet in Dover

4.84 out of 5 average rating, 202 reviews

The Mountain A-Frame at Mount Snow

Entire chalet-style A-Frame in Mount Snow with mountain views. Less than 1 mile from the base of Mount Snow and close to all the fun in the Green Mountains: AT access, swimming holes, covered bridges and more! Across the street you can hop on the Moover shuttle that takes you right to the mountain! 2 minute walk to market, coffee shop and local bar. 2 bedrooms + 1 loft, 1 bath, wrap around deck, cooking necessities, Smart TV and WiFi. You can find us on social (tag us!) @themountainaframe

Oct 14 – 21

$179 per night

Guest favorite

Chalet in Big Indian

4.95 out of 5 average rating, 107 reviews

The Alpine Chalet - A Cozy, Catskill Mountain Home

Enjoy the scenic Catskill Mountains in this Bavarian-style chalet situated on half an acre with valley views. Composed of modern luxuries and comforts, The Alpine Chalet is the perfect getaway for anyone looking to explore the Catskills. Only 6 mins to Full Moon Resort, 10 mins to Belleayre Ski Mountain, and 15 mins to Phoenicia/30 mins to Woodstock, an abundance of hiking trails, ski resorts, and charming towns await you! Follow us on Insta! @Alpine.Chalet STR License #2022-STR-AO-005

Aug 26 – Sep 2

$236 per night

Guest favorite

Chalet in Stoddard

4.95 out of 5 average rating, 195 reviews

Highland Haus- Cozy 70s AFrame- two wood stoves

Cozy 1975 A-frame chalet cabin sleeps 4 with a comfortable living space, two wood stoves, and a full kitchen. Located in the rural community of Stoddard. Enjoy the peace and quiet that this area has to offer. Many local hiking, swimming and fishing nearby. It is less than a 2-hour drive from Boston to the Highland Haus! Winter Guests- please note that Shedd Hill rd is very hilly and can be difficult to drive after a fresh snowstorm, all-wheel drive or 4-wheel drive is recommended.

Jul 11 – 18

$141 per night

Guest favorite

Chalet in Hunter

4.92 out of 5 average rating, 308 reviews

Big Timber Lodge - Hunter Mountain’s TOP Getaway

Discover why our guests have left over 275 five star reviews! This 3-story custom log home sits perched on a beautiful running creek for the perfect weekend or midweek getaway. Featuring a premium outdoor hot tub, fire pit area and truly unforgettable views. Our home offers two units each with three bedrooms, kitchen, indoor jacuzzi, fireplace and plenty of games. The staircase to the creek brings you steps away from a meditative nature walk, trout fishing and zen relaxation.

Dec 8 – 15

$956 per night