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).

Snug Chalet - Wi-Fi + Close to Mount Snow

This stylish 1971 chalet is a country retreat with modern comforts for you and your family... complete with strong WiFi and a fenced-in dog yard! The minimal cabin is tucked in the trees and set up for families and friends, pet & kid-friendly. 10-15 Minutes to Mount Snow 10-15 Minutes to Downtown Wilmington This is a country house, not a boutique hotel :) If booking during winter or spring months, we HIGHLY recommend a 4wd vehicle as the weather can cause some tough road conditions (snow/mud).

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

7min-Stratton Dogs OK Fire Pit EV Charger Arboreal

7min drive to pickleball, tennis, pool, golf, mountain biking and skiing @Stratton Resort. Soak up 13 acres of arboreal views from your private chalet. Light-filled w/ southern exposure. Deck and fire pit for stargazing, mid-century modern furnishings, new appliances, and 300Mbps Wi-Fi and a Mini Split AC/Heat. Convenient to ski areas, restaurants, shops, and swimming holes, yet secluded and quiet. Walk to Pikes Falls 29min to Bromley and Mt Snow AWD required for spring/winter. Pet fee $187.

Luxe Hot Tub, 8–12-Min Sauna, Stratton & Mount Snow

Escape to HYGGE HOUSE, your ultimate cozy & modern mountain getaway awaits. Come relax and make memories with family and friends in a luxurious modern retreat on 4 wooded acres in Stratton. Unwind in the private HOT TUB and SAUNA or relax in the rustic TREEHOUSE for the ultimate mountain getaway. Just minutes from Stratton Mountain and Mount Snow, this architectural gem is the perfect blend of seclusion and adventure. Features high-speed internet, a gourmet kitchen, and a cozy stone fireplace.

Secluded Lakefront Chalet•Firepit•Yard Dogfriendly

Just over an hour from NYC, this secluded, dog-friendly lakefront chalet offers 200’ of private shoreline, fenced yard and sunroom with serene lake views. Thoughtfully styled with collected pieces from my travels, it blends quiet luxury with modern comfort. Cozy up by the fireplace, enjoy vinyl or a movie, watch snowfall, spot wildlife, explore nearby trails, unwind by the fire pit and rest in the king-size bed. Romantic, peaceful, beautifully secluded – your perfect winter lake escape awaits.

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

Private Brook Chalet: Hot Tub, Fire pit, Mt. Snow

The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best food VT has to offer.

Highland Haus AFrame Lake Access Vintage 70s Charm

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.