
Holiday rentals in Hinsdale
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Top-rated holiday rentals in Hinsdale
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Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!
4.95 out of 5 average rating, 160 reviews
Forest Street Retreat Attached Guest House
Less than 1 mile from the Retreat Farm, this private & peaceful attached carriage house is perfectly located in the heart of Brattleboro. Only steps from the Retreat Woods nature trails & a short walk into historic downtown, you'll find coffee shops, bookstores & the Stone Church nearby. Thoughtfully designed to have a minimal cozy cabin feel, the downstairs is open concept living w/ a gas fireplace. Both bedrooms are upstairs. Outdoors, enjoy 10 miles of trails & the beautiful West River.
4.99 out of 5 average rating, 148 reviews
Cozy, Quiet Cottage on Country rd 2 mil from I-91
Our quite and comfy home is conveniently located less than 2 miles from I-91, but a 1/4 mile down a country road giving you lots of privacy. The cottage is less than a mile from Crump 'N Fox Golf; 2 miles from Northfield Mount Hermon; 10 minutes from Greenfield & Stoneleigh Burnham; 15 min to Brattleboro, Deerfield Academy, Bement & Eaglebrook; 20 min to UMass, Amherst & Northampton; 30 minutes to Keene NH & Shelburne Falls and 45 min to the Basketball Hall of fame in Springfield & Mt Snow VT.
4.88 out of 5 average rating, 371 reviews
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
4.85 out of 5 average rating, 167 reviews
Guilford Grove Cottage
Guilford Grove Cottage is a simple, comfortable small cottage on the threshold of the forest. A quiet and clean refuge with everything you need to relax in scenic southern Vermont. Prepare meals in the kitchen (breakfast supplies provided), relax on the loveseat, chill on the covered porch and enjoy being on the edge of nature; shoe-free and free from chemicals and artificial fragrances. Brand new construction. Easy access from I-91 & Route 2, 15 mins from Brattleboro and 20 to Greenfield, MA
4.97 out of 5 average rating, 149 reviews
Sweet Vermont Tiny Home Get Away
Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.
4.87 out of 5 average rating, 284 reviews
Healix Vermont Getaway
This charming turn of the century cottage has been mindfully renovated with warm colors and a meditative vibe. The space includes vaulted ceilings, large skylight, abundant oxygen providing greenery, and high end bathroom appointments. Referrals to local wellness and spa offerings provided. It's conveniently located off exit 1 on I-91, within walking distance of quaint downtown Brattleboro, with safe and free off-street parking. An entry ramp provides ease of accessibility for all.
4.94 out of 5 average rating, 282 reviews
Bright Garden View Apartment
Enjoy a unique stay at this central, beautifully-remodeled apartment in quaint Brattleboro, Vermont. The apartment is attached to the back of the charming 1914 home where I live, and has a private, separate entrance so guests can come or go as they please. This carefully-curated apartment includes tasteful design, a well-appointed kitchenette, organic cotton sheets, and natural bath products. Just off Hwy 91, the apartment is located in the quiet, historic neighborhood of Esteyville.
4.99 out of 5 average rating, 211 reviews
Peaceful and Private Farmhouse Retreat
Welcome to a peaceful New England farmhouse getaway, set among over 300 acres of conserved land, including wooded and meadow trails, just outside Chesterfield, New Hampshire. This spacious three-bedroom, two-bath farmhouse offers a rare blend of comfort, beauty, and quiet. Large windows throughout the home frame sweeping views of scenic fields and countryside, creating a light-filled, calming space that is perfect for families, couples, and small groups seeking a restorative stay.
5.0 out of 5 average rating, 3 reviews
Charming studio in renovated 19th century church.
This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.
4.95 out of 5 average rating, 644 reviews
Guest House @ 120
Unforgettable designer stay in the heart of downtown Brattleboro. Curated art, luxe finishes, and boutique comfort set this experience apart. Walk to the best cafes, boutiques, and galleries. Enjoy a chef’s kitchen, plush bed, quaint bath, and fast Wi-Fi. Every detail is elevated, every corner styled. Steps from Amtrak, wrapped in Vermont charm. Perfect for escapes, retreats, or inspired work. You won’t want to leave.
4.99 out of 5 average rating, 123 reviews
Private Brookside Farmhouse
Fully refurbished 1860's Cape on the site of an old water powered sawmill & small farm. Minutes from town and I-91 with a rural feel. 40 minutes to Stratton or Mt Snow. Private yard, lots of outdoor space, footpath to the brook. Brook sounds reach into the house when windows are open. Porch gets the AM sun, great spot for morning coffee, or just relaxing. Back yard with picnic table & barbeque grill.
4.93 out of 5 average rating, 88 reviewsPopular amenities for Hinsdale holiday rentals
Other great holiday rentals in Hinsdale

Barnside Cottage at Fruition Farm
4.95 out of 5 average rating, 44 reviews
The Blacksmith Shop of Vermont
4.93 out of 5 average rating, 15 reviews
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
4.98 out of 5 average rating, 46 reviews
Cozy Loft Cabin in Vermont with Sauna
5.0 out of 5 average rating, 33 reviews
Clean, Tranquil & Convenient | Dog Friendly!
4.85 out of 5 average rating, 78 reviews
Cozy Home with Relaxing Views
4.88 out of 5 average rating, 32 reviews
Bright, spacious country home
4.91 out of 5 average rating, 67 reviews
Log Cabin on Maple Sugar Farm
4.91 out of 5 average rating, 32 reviewsDestinations to explore
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- Okemo Mountain Resort
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- Monadnock State Park
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- Hildene, The Lincoln Family Home
- Mount Monadnock
- Emerald Lake State Park
- Bromley Mountain Ski Resort
- University of Massachusetts Amherst
- Massachusetts Museum of Contemporary Art
- Mount Sunapee Resort
- Mount Greylock
- Hancock Shaker Village
- Camp Plymouth State Park
- Mount Holyoke College
- Naismith Memorial Basketball Hall Of Fame
- The Montague Bookmill
- Jamaica State Park
- Worcester Polytechnic Institute





