Cottage vacation rentals in Dorset

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Top-rated cottage rentals in Dorset

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Top guest favorite

A spacious lawn is shown, featuring two buildings. One is a charming cottage with large glass doors, while the other is a main house with a traditional exterior. The ground is covered with fallen leaves, and trees line the background.

Cottage in Weston

4.97 out of 5 average rating, 102 reviews

Charming Mountain Cottage **NO CLEANING FEE**

Enjoy a charming cottage on the side of a hill in beautiful Weston, Vermont. You'll have the entire building to yourself (it's a stand-alone structure) to come and go as you please. My goal is to provide a five-star experience for five-star guests. I think little details like Ralph Lauren bath sheets, freshly-pressed bed linens, and duvet covers that are laundered between each guest make a difference. If you agree, you're probably the type of guest I'd enjoy hosting! Motorcycle friendly!!

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, 221 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.

Guest favorite

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, 278 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 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, 227 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.

Top 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, 405 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 cozy living area features a navy blue sofa positioned beside a bookshelf filled with books. A round wooden table is complemented by four wooden chairs. Natural light streams through multiple windows, emphasizing the warm tones of the interior.

Cottage in Manchester

4.81 out of 5 average rating, 117 reviews

Quintessential VT Cottage in Manchester Village

Enjoy a storied stay at the Lyman Cottage, a quintessential Vermont cottage in the heart of historic Manchester Village. Lyman Cottage affords a completely private getaway, only steps from the Equinox Resort with lots of space to relax and unwind. The cottage is located deep in the backyard behind the Wickham House. See our other listings for details. Amazing location -- 300 feet from the Equinox Resort, 5 minutes to Hildene, 15 minutes to Bromley and 30 minutes to Stratton.

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, 714 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 spacious bedroom features a skylight that allows natural light to fill the space. A bed is adorned with a colorful floral quilt, while a cozy armchair and table create a relaxing sitting area by glass doors that offer a view of the surrounding greenery.

Cottage in Newfane

4.97 out of 5 average rating, 138 reviews

Silk Purse Cottage on Baker Brook

The "Silk Purse" started life in the 60's as a 10x40 mobile home. Easy vehicle access and fast wifi are great for remote work. 20 minutes to Brattleboro, 30 to Stratton, 25 to Mt. Snow, 40 to Magic Mt. ski areas! The screened porch is a relaxing place to have coffee or cocktails. Extra windows add interior light in this shaded woodland setting, and a beautiful 12x14 addition with a skylight and a full wall of glass give an unobstructed, private view of the stream.

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, 201 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 cottage showcases a white façade and a metal roof, with blue shutters framing the windows. A colorful flower garden features various blooms, including irises and lush greenery, enhancing the welcoming approach to the entrance.

Cottage in Hartland

4.97 out of 5 average rating, 472 reviews

Breeze Hill Cottage

This cozy two bedroom cottage sits on a well-maintained dirt road overlooking fields, woods, and the NH mountains. Watch birds from the window, relax on the patio, and enjoy the flower gardens. The cottage boasts modern amenities mixed with antiques. Please note: if we don’t respond to an Airbnb message and you need to speak with us, call us!

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, 154 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, 133 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.