Chalet holiday rentals in Western Massachusetts

Peaceful VT Chalet w/ Mountain View’s

Our Peaceful chalet has everything you need. A fully equipped kitchen, 3 bedrooms, 2.5 baths, 2 living rooms, elec heat fireplace, outdoor fire pit, washer, dryer, Roku TV’s, great fiber optic internet. Accessible ATV/ snowmobile trails from property. 20 miles to Mt. Snow. Short driving distance to popular golf courses, shops, restaurants,breweries, kayaking, fishing, hiking, white water rafting ect An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

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

Chalet Sonsie: A Sweetwater Stay

Chalet Sonsie is a freshly-renovated waterfront getaway, where you can enjoy breathtaking views of Forest Lake year-round, from every room and all 3 levels of decks! Whether you're traveling with the kids, friends, or just looking for a quiet fishing retreat, there's something here for everyone. This cozy 2-bedroom home features 2 full kitchens, 1.5 baths, expansive fireplace and TV, plus a game room complete with foosball and mini-arcade! Book today, or check out other Sweetwater Stays! -Patti

StrautmanHaus: All-Season Chalet at Berkshire East

Welcome to StrautmanHaus, a Bavarian style A-Frame home, nestled at the base of Berkshire East Mountain Resort. This charming chalet is newly renovated, with 4 beds/2 baths/4 decks and stunning views that sleeps 10! Surrounded by mature growth pine trees, the property offers a perfect combination of privacy and ski-on/off access to Berkshire East. In the summer & fall, you have on-site access to the resort’s mountain biking/white water rafting/zip line/mountain coaster & aerial adventure park.

3BR/2BA Chalet w/ Unforgettable Views on 20+ Acres

A nature-lover's oasis, 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 (16 mi), Catskill (26 mi) and Hudson (29 mi), this is the ideal location from which to explore the best the Catskills has to offer.

Mountain View Retreat: 5 Mi to MT Snow, Hot Tub

Come escape to Wilmington, Vermont. Stunning views of Mt. Snow, a small stream, and a large hot tub on 12 secluded acres. Only 10 minutes to Mount Snow and 30 minutes to Stratton our home is the perfect getaway for your VT adventure with all of your family and friends. Come ski, snowboard, snowmobile, hike, kayak, mountain bike, swim, or fish just minutes away! After your long day exploring come relax in the hot tub, by the fire, in the game room, or just out on our deck taking in the sunset!

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

Ski, Raft & Relax | Lodge w/ Pool Table & Fire Pit

On your journey to The Lodge on Warner Hill, you will pass through a nostalgic covered bridge, drive by a babbling brook, and meander up a winding dirt road. Our home sits in a quiet, peaceful 5-acre setting. It has been completely remodeled with earth-tone charm. Enjoy your time with friends and family relaxing, reading a book, playing pool, barbequing on the back deck, gazing at the stars, or hanging out by the fire pit. Located 10 minutes from Berkshire East and the Deerfield River

Brook Haven Retreat - Minutes to Mt Snow&Stratton

Welcome to Brook Haven Retreat! We are situated directly on Wardsboro Brook, just minutes away from the best skiing and riding, hiking, biking, fishing and relaxation in Southern Vermont.The property features a private fenced yard and deck to take in all the beauty alongside the brook. The home is fully updated with modern conveniences including three sleeping areas, living room, and a fully stocked kitchen. We love and allow well-behaved furry friends in our home!

Highland Haus | Cozy 70s Aframe | Lake Access

Authentic 1975 A-frame chalet nestled in peaceful Stoddard countryside. This cozy cabin sleeps 5 with two wood stoves and full kitchen. Perfect rural retreat just 2 hours from Boston! Explore nearby hiking trails, swimming spots, and fishing areas. Summer bonus: complimentary canoe access! Highland Haus offers a tranquil escape with vintage charm. Note for winter visitors: Shedd Hill Road requires AWD/4WD due to steep terrain. Your cozy retro hideaway awaits!

Classic Vermont A-Frame | Fire Pit | Near Stratton

Escape to a classic Vermont A-Frame in Jamaica, Vermont on a private wooded 3-acre property along scenic Route 100. Near Stratton Mountain, Mount Snow, Jamaica State Park, and Pike Falls, this peaceful mountain retreat is perfect for hiking, swimming holes, fall foliage, scenic drives, and outdoor adventures. Enjoy mornings on the screened porch and evenings around the fire pit listening to the river across the street under the Vermont stars.

Modern Zen Chalet at the Foot of Gunks w Mt. View

Kick back at the foot of the Shawangunk Mountains in this calm, stylish home. Surrounded by forest, the house features large picture windows in every room to help you reconnect with nature. Enjoy the natural stone porch with a fire pit and newly built barrel sauna. Located near Minnewaska State Park, with quick access to trails, and views of Millbrook Ridge and the Gunks’ iconic climbing routes right from the windows.