Cottage vacation rentals in Dorset

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Top-rated cottage rentals in Dorset

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Top guest favorite
A rustic cottage is surrounded by vibrant flower pots, with a stone wall framing the entrance. A deck extends from the structure, featuring outdoor seating under a green umbrella. Trees provide shade in the background, while distant mountain views enhance the natural setting.
Cottage in Londonderry
4.96 out of 5 average rating, 225 reviews

Vermont Treehouse - Romantic Private Elegant

3 night minimum, unless prior approval, self checkin. Work remotely. This romantic, elegant, private getaway for two (or one) in our "Treehouse" with sleeping loft, full kitchen & bathroom, screened porch, deck, sauna, WiFi, BBQ grill, etc. Overlooking pasture & mountains. Enjoy the property with 3 miles hiking/snowshoe trails. Guest house on 160 acre private horse farm. Lots to do at nearby ski areas, shopping, hiking, biking, theater in summer. Or just relax. Discount for longer stays.

Superhost
The exterior of a wooden cabin is displayed amidst a snowy landscape. The structure features a sloped roof with skylights and a covered entrance that offers protection from the elements. A vehicle is parked nearby, and snow covers the ground and surrounding trees.
Cottage in Putney
4.82 out of 5 average rating, 284 reviews

The Cottage, a house built for guests.

In the village there is a wonderful farm to table restaurant, the Gleanery. A local pub, friendly, great food with indoor and outdoor dining & pub. The General Store, is the oldest continually run general store in Vt. The Next Stage, Yellow Barn, Sandglass Theater, these places provide an amazing collection of visual, musical, spoken word and world renowned art and artist to experience. These cultural event locations are but a mile away for the Cottage I hope you choose for your stay.

Top guest favorite
The charming guest cottage, with a light-coloured exterior and a metal roof, is surrounded by vibrant autumn foliage and wildflowers. A serene landscape of rolling hills enhances the rural setting, inviting outdoor exploration and relaxation.
Cottage in Pawlet
4.96 out of 5 average rating, 134 reviews

Carriage Barn at Indian Hill

Our guest cottage is a lovely converted 1840s-era carriage barn nestled in the heart of the Mettawee Valley in the southwest corner of Vermont. It is decorated with antiques, artworks and an upright piano. Our 65 acres on scenic Indian Hill are available for hiking & snow-shoeing. We have 12 acres frontage on the Mettawee River, rated one of the best for fly fishing in VT. Ready access to many area attractions, from local swimming holes to skiing at nearby Bromley and Stratton mountains.

Top guest favorite
The cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. A stone walkway leads to the entrance, while a covered wood storage area is visible nearby. Bright green leaves provide a natural canopy, creating a serene atmosphere.
Cottage in Whitehall
4.99 out of 5 average rating, 231 reviews

Hillside Cottage @ The Mettawee Retreat

The Hillside Cottage is a luxury cabin with views of the Mettawee River. Located on 26 acres on a back road, it is peaceful & private. Enjoy fishing, swimming, kayaking or relax on the deck. This riverside retreat includes a king bed, jacuzzi tub & a kitchenette. Sitting around the fire pit with dinner cooked on the grill is the perfect ending to a long hike. Whether it’s a quick get-away or an extended vacation, the Hillside Cottage is a simple solution from a complicated life.

Guest favorite
The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.
Cottage in Windsor
4.97 out of 5 average rating, 413 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Guest favorite
A quaint cottage is framed by vibrant autumn leaves, with a green metal roof contrasting the warm tones of the surrounding trees. A gravel driveway leads to the home, inviting guests to explore the peaceful nature setting.
Cottage in Dover
4.95 out of 5 average rating, 251 reviews

Cozy private cottage in the woods of Vermont

-The Ice Pond Camp, East Dover, VT A small well equipped cottage, surrounded by nature & quaint beauty. Enjoy southern Vermont's summer days as you relax, disconnect, recharge & spend your time living a slower pace in nature & rural beauty. Close to Wilmington (shopping, events and good food) and West Dover, (home of Mount Snow) and towns such as Putney and Brattleboro. Just minutes away are scenic villages, farms, brooks, ponds and lakes, walking trails & country roads.

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, 719 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated 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
A living area features a stone fireplace with a roaring fire, surrounded by large windows that invite natural light. A circular coffee table rests on a textured rug, while comfortable seating options include an upholstered chair and wooden accent chairs, complemented by soft lighting.
Cottage in Bennington
4.99 out of 5 average rating, 101 reviews

Cozy, bright 3-bedroom Cottage with fireplace.

Cozy, spacious brook-side cottage with 3 bedrooms, 2 baths, fully-equipped kitchen, fireplace, and serene, 382-acre country setting. Colorful artwork, designer furnishings, and well-appointed kitchen and bathrooms will make you feel welcome and at home. Historic charm of Bennington ten minutes away. NYC (182 miles); Boston (118); Mt. Snow (32); Prospect Mountain (13). Close to MASS MoCA (22), Tanglewood (49) and Manchester outlets (32).

Guest favorite
An open living area features rustic wooden beams and warm lighting. A cozy sofa is positioned near a wood stove, with a small dining table adjacent. The kitchen is visible in the background, showcasing appliances against a backdrop of exposed brick and wood floors.
Cottage in Dover
4.84 out of 5 average rating, 317 reviews

Cozy Camp in Vermont

This cozy camp located in beautiful East Dover, is on a secluded road off the beaten path where the babbling brook can be heard. Close to Mount Snow, Lake Whitingham, Lake Raponda, and only 25 minutes to Brattleboro the adventures are endless! Visit the serenity and beauty of Southern Vermont- especially in Fall during “leaf peeping”. This is a camp-style cottage with rustic charm. Snow tires are a MUST- Nov. - Apr.

Guest favorite
A serene landscape of a tranquil pond reflects a historic red building surrounded by trees adorned with golden foliage. Gentle hills rise in the background, while the sky displays a mix of light and shadow, creating a peaceful atmosphere.
Cottage in Pawlet
4.92 out of 5 average rating, 208 reviews

The Smithy Cottage at Consider Bardwell Farm

The historic “Smithy" at Consider Bardwell Farm is the original building used for blacksmithing by Consider Bardwell, himself, in the 1800s. Complete with brand-new, architect-designed kitchen and bathroom, wood-burning fireplace, and stone patio for outdoor grilling and dining, the Smithy is beautiful inside and out. Enjoy meeting our goats and all the local goodies and products that we can stock in your cottage.

Top guest favorite
The exterior of a red cottage is framed by greenery, featuring a welcoming entrance. A wooden ramp leads to the door, which has a glass panel for visibility. A sign identifies the property as Rollin Cottage, situated in a tranquil outdoor setting.
Cottage in Shaftsbury
4.97 out of 5 average rating, 157 reviews

Rollin Cottage

Welcome to Vermont! Rollin Cottage is a country cottage in a rural setting not far from the Village of North Bennington with a babbling brook, private patio and cottage gardens. Full kitchen, two bedrooms, ground floor master bedroom plus private loft bedroom with an additional sofa bed (full) in the living room. All amenities are provided.

Top guest favorite
A country cottage is positioned beside a tranquil pond, with vibrant green grass surrounding it. A rainbow arcs across the sky, adding a colorful backdrop to the serene landscape. Two blue chairs sit by the water's edge, inviting relaxation.
Cottage in Manchester
4.97 out of 5 average rating, 138 reviews

Home with a spring fed Koi pond and mountain view

Country cottage, full kitchen, closets, pantry, washer and dryer, with deck overlooking spring fed koi pond with mountain view. Open space kitchen/living room/dining area. Upstairs full bedroom with king bed, bathroom with shower, and walk in closet. Daybed in living room with pull out trundle bed. Pet friendly.

Popular amenities for Dorset cottage rentals

Quick stats about cottage rentals in Dorset

  • Nightly prices starting at

    Dorset vacation rentals start at G$25,105 GYD per night before taxes and fees

  • Verified guest reviews

    Over 280 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Dorset rentals

  • 5 Average rating

    Dorset stays are highly rated by guests—averaging 5 out of 5!

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