Vacation rentals in Dorset Hill

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Top-rated vacation rentals in Dorset Hill

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Top guest favorite
The rustic cabin features a red exterior with a metal roof, framed by lush greenery. Flower pots with colorful blooms adorn the porch, which includes a small table and chairs. Large windows allow natural light to illuminate the interior.
Cabin in Londonderry
4.94 out of 5 average rating, 367 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Guest favorite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry
4.95 out of 5 average rating, 214 reviews

Summit View Cottage:Apres Ski| Hot tub|Fireplace

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Superhost
A small red cabin is nestled under large trees, surrounded by lush greenery and autumn foliage. The backdrop features distant mountains, creating a serene and natural setting. Soft light filters through the leaves, enhancing the peaceful atmosphere of the landscape.
Guesthouse in Manchester
4.8 out of 5 average rating, 238 reviews

Glamping Cabin with Private Pond and Mountain View

This little glamping cabin with cozy woodstove is set at the far edge of a field overlooking a wildlife pond, seasonal fountain, and mountain. It is a peaceful place, surrounded by beauty, and special not just for these amenities but because it is improbably located on four private acres right in Manchester Center. The property abuts 70 acres of preserved land, but is steps from Main Street and all the shopping, dining, and outdoor options that this lovely year-round tourist town has to offer.

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 318 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favorite
A midcentury modern cabin is nestled among trees, its dark exterior contrasting with the fresh snow covering the ground. A spacious deck is visible, adorned with wooden railings, while large windows reflect the serene winter landscape.
Cabin in Shaftsbury
4.99 out of 5 average rating, 295 reviews

The Hygge Loft- mid-mod cabin on 70 forested acres

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Top guest favorite
The green barn structure features a deck with white railings, providing access through double doors. Lush grass surrounds the building, with trees framing the background. A gradient sky at sunset displays soft hues of pink and orange, creating a serene outdoor setting.
Barn in Manchester
4.99 out of 5 average rating, 290 reviews

Big Green Barn - Manchester Village Vermont

Unique Vermont Barn Experience! 1880s restored barn on 2 acres in Manchester Village across from Southern Vermont Arts Center. Converted to a photo studio in 2004 when we moved from NY; spacious, comfortable, solar-powered, approx. 1 mile to Main St. (town roads, no sidewalk), close to shopping, restaurants, golf, hiking, skiing, etc. Beautiful views, Mount Equinox front, the Green Mountains back. No pets. Not suitable for children under 12. (License number MRT-10126712)

Top guest favorite
An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.
Cottage in Shaftsbury
4.98 out of 5 average rating, 720 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

Top guest favorite
Cabin in Winhall
4.96 out of 5 average rating, 361 reviews

Dog Friendly A-Frame Retreat near Hiking, Skiing

The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 4 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe

Superhost
A modern cabin features a contrasting black exterior and wooden accents, nestled among lush trees. A wide deck with railing leads to the entrance, offering a welcoming space to enjoy the surrounding nature. Large windows provide ample natural light and views of the forest.
Tiny home in Athens
4.9 out of 5 average rating, 147 reviews

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

Top guest favorite
The exterior of a two-story house is visible, featuring a sloped roof and white siding. Lush green bushes frame the front yard, where a small decorative archway and white picket fence add charm. Surrounding trees provide a natural backdrop for the property.
Apartment in Manchester
4.99 out of 5 average rating, 290 reviews

Private two-bedroom suite within a two-story house

This is a private suite located on the second floor of a house. Separate entrance. The owners live downstairs. Great location with mountain views. Please note: 1) Our kitchen is fully equipped, but it has a hot plate instead of the traditional stove. 2) Instead of a full-size living room there is a small sitting area with a TV in the same area where the kitchen is located. 3) Guests don't have access to the backyard/patio.

Guest favorite
The historic two-story house features a blue exterior complemented by a white porch adorned with hanging flower baskets. A pathway lined with greenery leads to the entrance, enhancing the inviting appearance of the home surrounded by mature trees.
Guest suite in Dorset
4.9 out of 5 average rating, 201 reviews

Guest Suite in historic 1804 tavern, w/ Breakfast.

You'll have the whole 3rd floor to yourself with a new private bath, large bedroom with a/c, and a separate sitting room/library. Stay in an historic gem, listed on the National Register of Historic Places. Historically sensitive restoration has been done. You'll have a continental breakfast in the house's original dining room. We're a four a minute drive from the center of historic Dorset village.

Top guest favorite
A mid-century retreat is illuminated at dusk, surrounded by snow-covered trees. Floor-to-ceiling windows create a warm glow, inviting guests into the living space. The landscape features a serene atmosphere with gently falling snow, enhancing the peaceful setting of the property.
Home in Winhall
4.98 out of 5 average rating, 403 reviews

Stunning mid-century house on 2.5 private acres

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.

Popular amenities for Dorset Hill vacation rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Bennington County
  5. Dorset
  6. Dorset Hill