Vacation rentals in Dorset

Vermont cottage with water and mountain views

Welcome to our rustic, clean, cozy, quiet and comfortable guest cottage The open floor plan allows for a bright and airy living space Fully stocked chef's kitchen with new appliances Washer & Dryer Rustic hardwood floors with area rugs Beds: 1 full, 2 twin, 1 extra twin downstairs Outdoor 2 person swing overlooking serene water views of Deming Pond and the mountain backdrop Hiking, biking, alpine skiing, snowboarding, cross country skiing, snowshoeing Fully air conditioned and dog friendly

Riverbed Treehouse @hot tub & a new sauna & views!

The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

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!

Cozy Barn home w/ Mountain Views

Newly renovated cozy Vermont barn with views of Mount Equinox. This unique barn includes a full kitchen, bedroom, bath, smart TV, and wifi. Conveniently located 2.5mi to downtown Manchester and 3.7mi to the Dorset Town Green. Come hike, golf, ski, dine, shop, or take a stroll on the Manchester Rail Trail. 15min drive to Bromley and 25mins to Stratton. Relax with a cup of coffee or glass of wine on the deck while looking out at the mountains, or cozy up with a book by the electric fireplace.

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!

The Hygge Loft- mid-mod cabin on 70 acres w/HotTub

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Dorset Hollow Cottage

Cozy historic schoolhouse flooded with natural light located in the coveted Dorset Hollow. 2 bedrooms, 1 bathroom, high ceilings, terrace with babbling brook and mountain views, outdoor propane firepit and outdoor grill. Located 3 miles from Church Street in Dorset, 8 miles from Manchester Center, 23 miles from Stratton Mountain, 15 miles from Bromley Mountain, 8 Miles from Merck Forest and Farmland, 4 miles from the Dorset Quarry and 10 miles from Vermont Summer Festival.

Charming Vermont Schoolhouse

Kick back and relax in this calm, stylish space. A beautifully restored schoolhouse circa 1860 welcomes you. Situated on a quiet country road this adorable home on one wooded acre has lovely mountain views and a peaceful setting. Nearby you will find skiing, hiking trails and quaint Vermont towns with shops and restaurants. Manchester and Rutland are 30 min. drives, Dorset is just 20 min. Granville NY has a large grocery store and other shops and is only a 15 min. drive.

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Home in the Heart of Dorset Village

Nestled down a willow-lined drive this charming historic converted carriage house offers bucolic privacy in an ideal town setting. Unwind by the fireplace or out by the pond. Stroll to the bakery, general store, dinner and playhouse. The glory of the Northshire's hiking, farmers markets, skiing and swimming holes is within a scenic drive. The property borders the Dorset Field Club which offers groomed cross-country ski trails.

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.

Private Retreat Steps from Dorset Village Green

Private guest apartment in the heart of historic Dorset village. Spacious king bedroom with Hastens bed, leather reading chair, and ample closet space. Separate living room with comfortable, stylish seating, new TV and audio, lovely art and antiques. Kitchen area with counter dining space. Wood floors, lots of light and peaceful views to lawns and woodlands.