Vacation rentals in Dorset Hill

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Top-rated vacation rentals in Dorset Hill

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Top guest favorite

A welcoming porch features two white Adirondack chairs positioned around a small wooden table, adorned with a floral centerpiece. Potted plants provide a splash of color near the entrance, while warm light emanates from the cabin interior, hinting at a cozy atmosphere inside.

Cabin in Londonderry

4.94 out of 5 average rating, 348 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

A modern kitchen is showcased, featuring a central island with three wooden stools. The light wood and white walls create an inviting atmosphere. Windows offer natural light, and various kitchen items are neatly arranged on the shelves, emphasizing functionality and style.

Cabin in Londonderry

4.95 out of 5 average rating, 187 reviews

Summit View Cottage:Green Mtn views w/Hot Tub & AC

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

Top guest favorite

A spacious screened-in porch features several chairs arranged for relaxation. The wooden flooring complements the vertical wood panels of the wall. A door leads into the cabin, while a view of the yard and a distant structure can be seen through the screen.

Cabin in Jamaica

5 out of 5 average rating, 248 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Top guest favorite

Apartment in Dorset

4.99 out of 5 average rating, 188 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 favorite

A wooden door with a rustic finish is positioned at the top of a carpeted staircase. The door features a handle and a small window, allowing light to filter through. Soft lighting illuminates the stairway, leading to a welcoming entrance.

Apartment in Manchester

4.99 out of 5 average rating, 259 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, but you can enjoy the outside seating set in front of the house.

Top guest favorite

The exterior of a historic guesthouse is shown, featuring white siding and classic black shutters. The structure is located amidst lush green grass and trees, with a red barn visible in the background. A gentle sunset casts a warm glow over the scene.

Guesthouse in Wallingford

4.98 out of 5 average rating, 700 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

Top guest favorite

A front porch features two rocking chairs and a swing, surrounded by wooden logs. A decorative blanket drapes over a barrel, adding color. The natural wooded landscape is visible in the background, highlighting the tranquility of the cabin’s setting.

Cabin in Granville

4.98 out of 5 average rating, 183 reviews

Quaint log cabin nestled in the woods

Enjoy a break from the daily grind at this lovely tiny log cabin nestled among beech and ash trees. This tiny cabin provides peace and quiet on nearly 4 wooded acres just minutes from the town of Granville, NY. A full kitchen, living room, one bathroom and a loft bedroom complete with stackable washer/dryer provide a place to relax and soak in nature. The spacious front porch grants a protected outdoor space to watch the wildlife and enjoy the fresh air with your family and pup.

Top guest favorite

A set of double glass doors frames a scenic winter view, showcasing a snowy landscape with trees and distant mountains. Natural light filters through the panes, creating a bright and airy entryway. A wooden table with items sits beside the doors.

Barn in Manchester

4.99 out of 5 average rating, 280 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)

Guest favorite

Cabin in Winhall

4.96 out of 5 average rating, 352 reviews

A-Frame Mountain Retreat near Manchester

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 6 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

Guest favorite

A wooden structure with a steeply pitched roof is surrounded by lush green foliage. A light-colored pathway leads from the house to the entrance, integrating the building with the natural environment.

Tiny home in Athens

4.9 out of 5 average rating, 122 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.

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, 181 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.

Superhost

A window view offers a serene panorama of rolling green fields and distant hills. Soft colors of the sky reflect the time of day, while a wooden countertop supports two black chairs, inviting a moment of relaxation while enjoying the scenic landscape.

Bus in Granville

4.88 out of 5 average rating, 144 reviews

Serene Bus Getaway Among Rolling Farm Land

Tucked off a quiet dirt road, this stationary bus promises to provide you and yours an unforgettable accommodation for your next Upstate NY retreat. Come stay in the Sleepy Tire, and wake up to beautiful views of Vermont’s Green Mountains, an indoor bathroom with flushing toilet and hot shower, and WiFi so you can stay connected to those that matter.