
Cottage vacation rentals in Dorset
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Top-rated cottage rentals in Dorset
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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.

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.

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.

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.

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.

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.

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.

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).

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.

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.

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.

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
Cottage rentals with a hot tub

Cute Cabin! Plymouth, Vermont.

Modern Cottage between Stratton and Mount Snow VT

Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace

NEW Guest Cottage on 23 Acres

Cozy Killington Getaway • Hot Tub + 5 min from Mt.

Country Chalet, HotTub, 8 Mins to Skyeship Gondola

Newly Renovated, Hot tub, 2min to Killington lift

3BR lakefront with dock, swim platform, & firepit
Pet-friendly cottage rentals

Quaint stone house!

Adorable Dog Friendly Cottage w/FIOS

Private cottage in the woods

Idyllic Lake Cottage | Bay Views | Cozy Fireplace

50 Acres of solitude & 1/2 mile on the West River

The Cottage in East Poultney

Cozy Vermont Antique Sugar House with Fireplace

Cottage-7 min to Ski Stratton-Woodstove-View-DogOK
Private cottage rentals

Cozy Country Cottage

Stone Wall Cottage, Stonewall : GMHA, Okemo

The Crik House: modern digs, American farm country

Idlewild Cottage on Star Lake Near Okemo

Charming New England Cottage

Cottage w/ Loft near VT, Cambridge, Salem

Riverside Cottage - Bridgewater Vermont

No Frills Lakeside Cottage, EZ access, Row Boat
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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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Saratoga Spa State Park
- West Mountain Ski Resort
- Fort Ticonderoga
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Lake George Expedition Park
- Peebles Island State Park
- Dorset Field Club
- Hildene, The Lincoln Family Home
- National Museum of Racing and Hall of Fame
- Hooper Golf Course
- Bromley Mountain Ski Resort
- Northern Cross Vineyard
- Autumn Mountain Winery
- Brattleboro Ski Hill