Holiday rentals in Hinsdale

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Top-rated holiday rentals in Hinsdale

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Guest favourite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford

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
Top guest favourite
An open living area features two patterned sofas arranged around a natural wood coffee table. A small lamp provides soft lighting, while a gas fireplace adds warmth. Light streams in through a window, with sheer curtains framing the view.
Cottage in Brattleboro

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
Guest favourite
A wooden deck overlooks a serene lake, featuring a round glass table with a central umbrella. A charcoal grill is positioned nearby, surrounded by trees that enhance the natural setting.
Chalet in Winchester

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
Top guest favourite
Home in Guilford

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
Top guest favourite
Treehouse in Wilmington

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
Top guest favourite
The exterior of a renovated cottage is depicted, featuring natural wood siding and a welcoming porch. Vibrant garden flowers and greenery surround the entry, contributing to a serene atmosphere. A large window invites natural light, while a solar panel is visible on the roof.
Bungalow in Brattleboro

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
Top guest favourite
A spacious sleeping area is highlighted by large windows dressed in soft curtains, allowing natural light to fill the room. The bed features a checkered blanket with decorative pillows, paired with a simple side table and a small plant, enhancing the cozy ambiance.
Flat in Brattleboro

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
Top guest favourite
The garden features raised vegetable beds surrounded by a wooden fence. In the background, the charming former church building with a pointed steeple is visible, framed by vibrant autumn foliage in shades of red and orange.
Guest suite in Brattleboro

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
Top guest favourite
Flat in Brattleboro

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
Guest favourite
An enclosed porch is furnished with a white rocking chair and various seating options adorned with colorful cushions. A woven storage box sits beside a patterned area rug that features large floral designs. Natural light filters through multiple windows, creating a bright atmosphere.
Flat in Brattleboro

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
Guest favourite
A bright hallway extends through the upper level, featuring exposed wood beams and soft yellow walls. Vintage framed artwork is displayed alongside a small table with fresh flowers. A doorway leads to a cozy space lined with bookshelves, inviting quiet reading moments.
Barn in Guilford

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
Top guest favourite
The entrance features a covered porch with a red bench and potted flowers in vibrant colors. A welcome mat leads to the front door, framed by two red columns. Seasonal decorations add charm to the welcoming facade.
Guest house in Chesterfield

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 reviews

Popular amenities for Hinsdale holiday rentals