Guesthouse vacation rentals in Rutland County

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Top-rated guesthouse rentals in Rutland County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
A charming guest house is depicted, characterized by its red siding and gabled roof. An American flag is displayed at the entrance, while a covered porch features seating options. Lush green grass and trees frame the property, adding to the serene landscape.
Guesthouse in Leicester
5 out of 5 average rating, 23 reviews

Peace of the Farm Guest House

Forget your worries in this spacious and serene space. Located on 57 acres of pastures, hayfields and woods, our guest house sits central on Foxcroft Farm and is situated about 800' from the main road, down the driveway past our house, barns and gardens. The farm is about 5 miles from Brandon, 3 miles to Lake Dunmore, 12 miles to Middlebury, 45 minutes to Killington or Lake Champlain ferries/ bridge to NY State. Biking, hiking, kayaking, boating, fishing, skiing, local wineries, beers, arts...

Top guest favorite
The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.
Guesthouse in Granville
4.91 out of 5 average rating, 950 reviews

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Top guest favorite
The kitchenette is designed with light-colored cabinetry and a large wooden countertop. Appliances include a microwave, toaster oven, and coffee maker, while a two-burner cooktop is available for cooking. Natural light enters from a nearby window, illuminating the cozy dining area with wooden chairs.
Guesthouse in Mount Holly
4.96 out of 5 average rating, 77 reviews

Moon Acre Farm Green Mountain Oasis - near Okemo

Relax in the mountain stillness, overlooking a pond in a stylish studio guesthouse at Moon Acre Farm. Our guesthouse is off of the main roads, surrounded by 60,000 acres of National Forest, yet 15 miles drive to restaurants, shopping, and boating. The studio is open and spacious (900 sqft), and artistically built into the upper level of our barn to take advantage of the views of the mountains and pond. Enjoy sitting on the balcony overlooking a stream or explore the gardens and woods.

Top guest favorite
A charming guesthouse with a red exterior is set against a backdrop of vibrant greenery and colorful flower beds. Various flowers in shades of orange, pink, and purple border the property, while tall trees provide natural shade. The tranquil setting invites relaxation in nature.
Guesthouse in Wallingford
4.98 out of 5 average rating, 740 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

Guest favorite
Snow-covered landscape is showcased, featuring a mix of bare trees and evergreens. A path is visible winding through the snowy terrain, leading towards distant hills under a clear blue sky.
Guesthouse in Andover
4.89 out of 5 average rating, 107 reviews

Quiet Self Contained Apartment in Vermont Hills

Large self contained studio apartment on 30 acres of woods in Vermont's South Central skiing and hiking hills. Apartment has own entrance and has fully equipped kitchenette. Sleeps four comfortably. Very quiet at the end of a dead end road. 15 mins to Okemo, Bromley and Magic ski areas, 30 mins to Stratton, 40 mins to Killington. Extensive hiking and snowshoeing trails from the property. Charming village of Weston and Vermont Country Store 5 mins away.

Top guest favorite
A charming cottage is nestled amidst lush greenery, featuring a welcoming porch with an umbrella. The American flag flies above, and a serene pond reflects the surrounding landscape, creating a peaceful atmosphere. Natural stone formations border the water's edge, enhancing the outdoor space.
Guesthouse in Granville
4.98 out of 5 average rating, 64 reviews

Little Falls Cottage

Escape and unwind at our peaceful, romantic 2-bedroom, 1-bath cottage with private waterfall on a spring fed creek. Take a hike on our wooded 32 acres. Relax and barbecue on the deck or sit by the creek-side fire pit. Prepare a romantic dinner and spend a quiet evening in front of the fireplace or fall asleep to the sound of waterfalls. Enjoy year-round activities at nearby ski centers, lakes, and in the scenic mountains of New York and Vermont.

Top guest favorite
A comfortable living room is presented, featuring two patterned armchairs and a dark sofa. A coffee table occupies the center space, with side tables and lamps positioned strategically. Natural light filters through the windows, while a ceiling fan offers a cooling breeze.
Guesthouse in Plymouth
4.97 out of 5 average rating, 106 reviews

Quiet Couples Retreat near Killington and Okemo

Clean and comfortable rural guest house in quiet and serene setting on 68 acres of land in Plymouth on Vermont Route 100, a top 10 scenic road in the US. Only 15 minutes from Killington and Okemo and minutes from hiking, lakes, fishing, boating, swimming, and a state beach and boat landing. Historic Woodstock is 15 miles away. Guests must be 21+. Inquiries from guests with no prior reviews on Airbnb will be further screened.

Top guest favorite
A living area features a light grey sofa adorned with two decorative pillows, situated on a textured area rug. A wooden dining table and black chairs are visible nearby, while a wall-mounted sign adds a personalized touch to the warm-toned space.
Guesthouse in Castleton
4.97 out of 5 average rating, 360 reviews

Bomoseen Bungalow

Located near Lake Bomoseen and Castleton University. This is a charming upstairs apartment in a quiet, residential neighborhood. Walking distance to boat rentals and to a local country store. This apartment provides you with a cozy stay - a bedroom with a queen size bed, sofa bed, and air mattress. There is Roku television, a heat pump for air conditioning or heat, Keurig coffee maker, and more. This is a non smoking unit.

Top guest favorite
An open living area features natural wood paneling and a high ceiling with exposed beams. Two comfortable sofas are arranged around a coffee table. Light fills the room from multiple windows, enhancing the spacious feel. A dining area is visible in the background.
Guesthouse in Poultney
4.94 out of 5 average rating, 32 reviews

Large Loft Apartment

Large (1600 sq ft) private apartment on 132-acre property. Roomy, comfortable space with high-speed internet is ideal for a family or a couple with pets. Rural escape just steps away from the Delaware & Hudson rail trail where you can bike, walk or ski to two charming small towns. Conveniently located only 5 miles to local lakes, 20 miles to Rutland and 33 to Killington. Kitchen has all the essentials for your cooking needs.

Guest favorite
A cottage with a metal roof is set on a landscaped lot, featuring a gravel pathway and well-tended flower beds. A front deck with two chairs offers an inviting spot for relaxation, while trees provide visual interest in the background.
Guesthouse in Castleton
4.92 out of 5 average rating, 13 reviews

Elegant Lakefront one bedroom cottage

Enjoy lake living at this cottage/carriage house. Eastern shore of Lake Bomoseen for fabulous sunsets. Great swimming right off our dock. Adjacent to Crystal Beach. Near hiking trails and great biking. 30 minutes to Killington, Pico or Okemo for skiers. The cottage has a beautiful and well equipped kitchen to prepare gourmet meals! Dishwasher, washer/dryer, heated towel rack in the bathroom.

Guest favorite
The interior of the cabin features a spacious bed covered with a floral-patterned comforter. Large windows provide views of the surrounding woods, allowing natural light to fill the space. Accents include lamps on bedside tables and woven décor elements for a cozy atmosphere.
Guesthouse in Granville
4.9 out of 5 average rating, 71 reviews

Pretty pondside camping cabin with double bed

Enjoy the lovely setting of this cute cedar cabin on a small spring-fed pond. Semi-private, with a composting toilet in the garage. This is a wooded property, with a log home and 2 cabins. Paths all around the site are perfect for forest bathing.

Guest favorite
The exterior of a red cabin is framed by green grass and colorful yellow flowers. The building features multiple windows and a gabled roof, creating a charming and rustic appearance. A clear pathway leads to the welcoming front door.
Guesthouse in Pawlet
4.91 out of 5 average rating, 337 reviews

Picturesque Cabin on the Mettowee

This beautiful cabin features a loft style sleeping area, full bath, full kitchen, sitting area, and incredible views of the Mettowee River. Enjoy nature just outside your door with gorgeous views of fall foliage, fishing on the river and hiking.

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