Vacation rentals in Dorset

Romantic Barn Guesthouse in Village Center

Keep it simple at our peaceful and centrally-located hideaway. This rustic and cozy two-story barn guesthouse with fireplace is located on four acres of a 1768 historic homestead right in Manchester Center. Enjoy the pond and mountain views from the bedroom and living room windows; the guesthouse faces a peaceful meadow and wildlife pond which abuts 70 acres of preserved land with hiking trails, yet it's also just steps from Main Street and all of the dining and shopping of Manchester Village.

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

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.

Waterfront Vermont Lake House w/ Panoramic Sauna

Waterfront on Lake St. Catherine, with almost 100ft of private lake frontage and a view that's hard to beat. Watch the sunrise from the deck or from inside our new panoramic barrel sauna. Explore the lake by kayak or canoe — both included for guests. Keep an eye out for both bald eagles and loons. There's also a fire pit for evening s'mores — firewood included as well. Great for families — we've got a crib, a bunk room for the kids, and a bookshelf of board games for those rainy days.

Cow Barn Lodge

Our home is located in MT. Tabor, Vermont, just off of Route 7, in a country setting with beautiful Mountain views of the Green Mountain National Forest, Dorset and Danby Mountains. The house is an old barn converted into a beautiful spacious home, on 4 acres. Snowmobiling from our place, plus 4 major ski areas less than 30 miles away. Hiking, fishing, swimming, golfing, and the Equestrian horse show are all nearby. as well as shopping in nearby Manchester and Rutland Vermont.

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

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.

Classic Vermont Home with Mountain Views.

Discover classic New England charm at this beautifully updated 3-bedroom country home on Dorset West Road. Enjoy a cozy fireplace, modern kitchen and bath, and serene mountain surroundings—all just moments from the Dorset Green, hiking trails, and the shops and restaurants of both Dorset and Manchester. This property is administered by Marble House Project, an non-profit artist's residency, and income from the property goes to support the program.

Dorset, Vermont mountain retreat

Relax at this peaceful, private and welcoming Dorset condo with a fireplace and spacious deck with views of the mountains. Get away from the hustle and bustle of everyday life. Sit by the fireplace and read or enjoy mountain views from the deck. Grill outside or sit indoors at the country table with family and friends. Dorset and environs (Manchester, Bromley, Stratton, Arlington) offer a number of excellent restaurants, shopping, and sports.

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.