
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, 161 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, 149 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
Beautiful timber-frame treehouse
The timber frame treehouse is a perfect couples retreat. The home is custom built with hardwood maple trees cut down and milled right on the property. The deck has a barrel sauna, cold or hot cedar soaking tub, a propane fire pit, a wood burning chiminea fire pit, and a bar top for outdoor dinning. The inside has a stone fireplace, fully equipped kitchen, tile shower, projector with dvds, books, board games, chandelier, and dimmable lighting for any mood. This home is truly one of a kind.
5.0 out of 5 average rating, 124 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, 286 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
River View apartment
Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .
4.99 out of 5 average rating, 205 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
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
Log Cabin: Amazing Views, River Frontage, Hot Tub
A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.
4.99 out of 5 average rating, 320 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
Quiet St in Town, gardens, terrace
Private entry, up wide covered stairs to open and enclosed porches, into newly renovated spacious open concept living and kitchen area. Separate large BR with queen-size bed has French doors that open onto the enclosed porch. A few blocks to downtown restaurants, food coop, and shops, walking distance to trails.
4.9 out of 5 average rating, 423 reviewsPopular amenities for Hinsdale holiday rentals
Other great holiday rentals in Hinsdale

The Blacksmith Shop of Vermont
4.93 out of 5 average rating, 15 reviews
Private Brookside Farmhouse
4.93 out of 5 average rating, 88 reviews
The Beam House | Cozy Rustic Retreat in Winchester
4.89 out of 5 average rating, 28 reviews
Cozy Home with Relaxing Views
4.88 out of 5 average rating, 32 reviews
Peaceful and Private Farmhouse Retreat
5.0 out of 5 average rating, 3 reviews
Barnside Cottage at Fruition Farm
4.95 out of 5 average rating, 44 reviews
Casita by the Green: Quiet, Country, close to town
4.94 out of 5 average rating, 77 reviews
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
4.98 out of 5 average rating, 46 reviewsDestinations to explore
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- Okemo Mountain Resort
- Stratton Mountain
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Bousquet Mountain Ski Area
- 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





