Villa holiday rentals in Rutland

100 yrs old 2024! Historic Musician's Villa Bolton

This truly intriguing turn-of-the century home transports guests to the inspiring mood & enduring character of the great & gracious. Built by a legendary musician’s family w/focus on elegant entertaining, this 100 yr old home is ready for guests after 3 yrs of restoration. Remaining true to original form, guests find showpiece architectural acoustics in great room, elevated framework throughout w/timeless archways, dramatic stairway w/ornate balustrade, romantic rounded walls, relaxing patios.

Gorgeous Victorian-Style House w/ Hilltop Pool!

Nestled in a serene valley of the Green Mountain National Forest and boasting 5 acres of maple tree-laden land, this Victorian home is the place for an unparalleled retreat. The 6-bedroom, 3.5-bath vacation rental was built in 1856 and boasts a perfect blend of old-fashioned charm and modern luxury. Spend your days relaxing at the river on-site, taking a dip in the pool, or roasting s'mores at the fire pit. During winter, curl up with a book in the library and gaze out over a snowy hillside.

Stonehouse at Stratton

Create cherished memories in this unique, family-friendly haven. Designed for entertainment, enjoy a wet bar, pool table, ping pong, darts, and more. Heated floors and Bluetooth sound systems add luxury. Each bedroom has a private bath. The expansive kitchen accommodates the entire family, and a fireplace invites warmth after skiing or boarding. Revel in privacy on 4 acres, with a 2-car heated garage. Only minutes from Stratton, this home offers comfort and leisure in every detail.

Vermont Villa Near the Trails

You'll be able to enjoy panoramic views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

Villa with Pool + Fitness Center Access

Enjoy stunning views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

Sun Castle Resort - Luxury Lakefront Villa

Reminisce about vacationing on the Lake in one of our luxury Villas. Includes occupancy of up to 4 guests with two king bedrooms one queen pull out sofa sleeper and a kitchenette. Lake George Village is 1.25 miles from the property

Whiffletree base of Killington outdoor pool

Whiffletree C2 has been totally renovated and looks great. Located at the base of Killington close to mountain biking and snow sports.

Whiffletree B8 Great location with shuttle bus to

Whiffletree B8 Great location with shuttle bus to base lodges and ski home

Whiffletree base of Killington outdoor pool

Whiffletree F6 is on the shuttle bus route with a ski back trail