Guesthouse vacation rentals in Rutland County

Wildcat Guest House - 4-Seasons Couple's Retreat

Our Guest House is on the VAST system, offering true ride-in, ride-out convenience and ample parking for snowmobile trailers. We are located less than 20 miles from Pico and Killington Ski Resorts. Although the property is off-grid, the studio offers modern amenities, including electricity, high-speed internet, and a large-screen TV. Note: This is an adults-only (18+) property for singles/ adult couples seeking a peaceful, relaxing retreat. It is not suitable for children or guests under 18.

Spacious studio on 200-acre farm

Spacious and comfortable studio on 200 acre farm. Peaceful country setting 15 min. from Rutland/Killington; 10 min to Mountain Top Resort. Access to miles of hiking and biking trails. Two Swedish sleeping boxes with queen beds. Desk to work from home. Oversized sofas. Storage space. Heated floor in tiled bathroom. Granite countertops, cherry cabinets. Two-burner induction stove top. Combo convection/microwave. SmartTV for your streaming service. High speed wi-fi. Outdoor seating and grill.

The Black Sheep Barn

The historic Black Sheep Barn is located in beautiful Ludlow less than a mile to Okemo Mountain Resort. The renovated space formally part of the barn is located in the Village and offers a private location within walking distance to boutiques, restaurants, shopping and Dorsey Park. The guest part of the Barn is facing the large, deep, private yard and has a courtyard with a firepit exclusively for guest use. There is plenty of parking adjacent to the space.

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.

Slopeside Estate Guesthouse: Ski On/Off, Hot Tub

This standalone 3BR, 2BA guesthouse offers direct ski-in/ski-out access on Killington’s Great Eastern Trail. Enjoy a private hot tub, BBQ grill, & deck with stunning views. The cozy living area includes smart TV & high-speed Wi-Fi, while the fully equipped kitchen makes meal prep easy. Bedrooms are spacious & we're pet-friendly. Perfect for families or groups, close to skiing, hiking, & Killington attractions. Book now for the ultimate mountain retreat!

Little Falls Cottage

Escape and unwind at our peaceful, romantic 2-bedroom, 1-bath cottage with private waterfall and natural pools. 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.

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.

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.

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.

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.

Private Apartment on 8 Acres

A furnished efficiency apartment located on the second floor of a free standing garage located 100 yards away from the main house. The property is on 8.5 acres with a river, two stocked ponds and boarders the Moosalamoo National Park.

Beautiful Guest House near Bromley, Magic, Okemo

Beautiful 1 bedroom guest house near Bromley, Magic, and Okemo. Open space with high ceilings and plenty of light. Perfect for a ski vacation, fall foliage trip, or enjoying the beautiful perennial gardens in spring and summer.