Holiday rentals in Dorset Hill

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Top-rated holiday rentals in Dorset Hill

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Guest favourite
The exterior of a red wooden house is showcased, surrounded by lush green grass and trees. A neatly trimmed garden features colorful flowers, while a small shed is visible in the background. Pebbled pathways provide access to the home's entrance.
Flat in Mount Tabor
4.93 out of 5 average rating, 117 reviews

Vermont Ski/Okemo/Killington/Pico/Stratton/Bromley

We welcome you to come experience Vt. We are a quiet, private, cozy, clean, stay in the country. Located equal distances to all surrounding towns and ski areas. Drive the Green Mountain National Forest road #10 to Peru, Landgrove & Weston. Hike on the Appalachian and Long trail. Fish, bike, forage, swim and spelunk (caving) Dine & shop, Manchester, East Dorset, Wallingford & Rutland. Walk around Danby. Take a scenic drive to Pawlet & Dorset. Ski, Killington, Pico, Okemo, Bromley, Stratton.

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.
Guest house in Manchester
4.8 out of 5 average rating, 242 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 favourite
The entrance of the Bonnet St Barn features a deep red exterior with a sloping roof and an overhang. A small chair is positioned beside the door, framed by lush greenery and blooming flowers, enhancing the welcoming entryway.
Flat in Manchester
4.99 out of 5 average rating, 103 reviews

Bonnet St Barn

Keep it simple at the peaceful, cozy and centrally-located Bonnet St Barn. Conveniently located steps from Manchester’s landmark 'Northshire Bookstore', restaurants and delightful shopping. The apartment is on the main floor of the two-story barn and features a king-size bed, a smaller second bedroom with a twin bed, AC, high speed WiFi, TV and a full kitchen for relaxing mealtimes. Less than 30-minute drive to Bromley & Stratton ski areas. Enjoy the Green Mountains of southern Vermont!

Top guest favourite
Flat in Dorset
4.99 out of 5 average rating, 193 reviews

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 4 friendly horses, entertaining chickens, mountain views and a host who cares about you. The farm is a quiet, private, peaceful place with 30 acres to roam, but still close to Dorset and Manchester. Fields, mountains and a pond are all here. Good for couples and solo travelers who want an amazingly beautiful setting. This listing is more than a rental... it's an entire farm. Powered by solar to help the planet!

Top guest favourite
An open living space is depicted, featuring a kitchen area with a stove and a kettle. A cozy sofa is positioned nearby, with large windows allowing natural light to fill the room. A staircase leads to a sleeping loft, visible above, with a unique railing design.
Guest suite in Manchester
4.91 out of 5 average rating, 153 reviews

Bright Manchester Studio with Sleeping Loft

Our studio apartment with sleeping loft is great for two adults or a couple with children. Located on a quiet country road great for taking long walks. There is a queen bed in the loft and a pull out queen sofa in the living area. Bright with high ceilings and all new furnishings. We are less than three miles from town, 20 minutes to Bromley and 25 minutes to Stratton. Close to hiking, biking, fishing, great restaurants and shopping. Please note;Owners lives on premise in main house.

Top guest favourite
A cozy living area features a mixture of seating options, including a tufted sofa and a vintage-style sofa adorned with decorative cushions. Natural wood floors enhance the warmth of the space, while artwork on the walls and a circular coffee table complete the inviting atmosphere.
Barn in Chester
4.99 out of 5 average rating, 710 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

Top guest favourite
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, 292 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 favourite
Cabin in Winhall
4.96 out of 5 average rating, 367 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

Top guest favourite
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.
Flat in Manchester
4.99 out of 5 average rating, 298 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.

Top guest favourite
Flat in Poultney
4.94 out of 5 average rating, 376 reviews

Cozy Poultney Village Apartment

I enjoy booking my two-story in-law apartment with a private entrance, which is attached to my 1850 Poultney Village home. I am located a block from Main Street with shops, books, and eateries. I am in the lakes region of Vermont, close to both Lake St. Catherine and Lake Bomoseen. Killington is 35 miles away. We am also located a mile from the NY border and the entrance to Lake George and the Adirondacks.

Top guest favourite
A spacious room features dark blue walls and ample natural light from large windows. A cozy bed is complemented by a comfortable seating area with a sofa and armchair. A wooden coffee table holds flowers, and wall art adds character to the space.
Guest suite in Salem
5 out of 5 average rating, 101 reviews

Suite on Salem

Keep it simple at this peaceful and centrally-located place. Walking distance to Salem Central, Fort Salem Theater, the Historic Salem Courthouse, Jacko's, Salem Art Work, On a Limb Bakery, and more. Come stay in our secure 2-room suite plus bathroom with a separate entrance uniquely filled with local art and antiques. Includes cube-sized refrigerator, coffee maker, and microwave for use.

Top guest favourite
The house is set amidst lush greenery, showcasing a modern design with a large metal roof and multiple windows. Grassy areas surround the property, with trees providing a natural backdrop. A rainbow is visible in the sky, adding a touch of color to the serene rural landscape.
Guest suite in Salem
4.98 out of 5 average rating, 127 reviews

Hilltop Country Views Studio Apartment

Enjoy a relaxing stay in the country. Easy access to Vermont & Saratoga. Eat local produce. Fresh eggs, bread and butter or oatmeal for your first breakfast, coffee and tea provided. Go shop, ski, hike or stay put & enjoy a good book! (After you're confirmed, please let us know if you're vegan, and or glucose or lactose intolerant.)

Popular amenities for Dorset Hill holiday rentals

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