
Holiday rentals in Hinsdale
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Hinsdale
Guests agree: these stays are highly rated for location, cleanliness and more.

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
The Blacksmith Shop of Vermont
Experience the perfect blend of historic charm and modern luxury in this beautifully converted Blacksmith shop, nestled in the scenic pastures of Southern Vermont. Pet and family friendly, this retreat spans three levels. The lower-level bedroom offers a king bed, half bath, and patio access. The main floor boasts a fully equipped kitchen and spa-style bath. Upstairs an airy loft bedroom provides a king bed, ample storage, and a cozy ambiance, ideal for a sophisticated yet relaxing getaway.
4.94 out of 5 average rating, 16 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
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, 212 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
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 reviews
The Carriage Barn
Situated on a 1792 Vermont farmstead, the original Carriage Barn is a thoughtfully renovated 2-bedroom cottage that blends historic charm with colorful, comfortable design. Located just 10 minutes from Brattleboro and all that Southern Vermont has to offer, it’s a perfect home base for a cozy New England escape.
4.99 out of 5 average rating, 139 reviews
House on a hill
Keep it simple at this peaceful and centrally-located large studio home. Enjoy your coffee while sitting on the screened in porch with beautiful local views. Just 3 miles to Brattleboro, VT and 12 miles to Keene, NH you can spend the day hiking in VT and the night in downtown Keene.
4.98 out of 5 average rating, 115 reviewsPopular amenities for Hinsdale holiday rentals
Other great holiday rentals in Hinsdale

Peaceful and Private Farmhouse Retreat
5.0 out of 5 average rating, 3 reviews
Casita by the Green: Quiet, Country, close to town
4.94 out of 5 average rating, 77 reviews
Cozy Home with Relaxing Views
4.88 out of 5 average rating, 32 reviews
Private Brookside Farmhouse
4.93 out of 5 average rating, 88 reviews
Barnside Cottage at Fruition Farm
4.95 out of 5 average rating, 44 reviews
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
4.98 out of 5 average rating, 47 reviews
Cozy Loft Cabin in Vermont with Sauna
5.0 out of 5 average rating, 34 reviews
Peaceful forest cottage getaway
5.0 out of 5 average rating, 85 reviewsDestinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Jersey City Holiday rentals
- Portland Holiday rentals
- Newark Holiday rentals
- Mont-Tremblant Holiday rentals
- Salem Holiday rentals
- Atlantic City Holiday rentals
- Providence Holiday rentals
- Okemo Mountain Resort
- Stratton Mountain
- Jiminy Peak Mountain Resort
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Monadnock State Park
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Mount Monadnock
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- 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
- Bridge of Flowers





