Villa holiday rentals in Rutland

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Top-rated villa rentals in Rutland

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Private room in Windsor

4.88 out of 5 average rating, 33 reviews

Private Wing of largest Colonial Mansion in US

Built in 1902 and comprehensively renovated in late 2016, the Windsor Mansion is an incredibly well preserved example of Colonial Revival Architecture. Filled with elegance & history, Three US Presidents have slept here. Our 17 Rooms/Suites are individually decorated each with private bathroom & free wireless internet. Set on 14 acres with a tiered terrace offering spectacular views & a custom fire pit. Lots to see in area including Saint-Gaudens Nat'l Park, Quechee Falls, Dartmouth College, etc

Villa in Woodstock

4.8 out of 5 average rating, 5 reviews

Woodstock/Barnard Chalet 20 min Killington dog ok

Rarely Available estate - Nightly, Weekly or monthly stays available for winter 2024-5. Our 5 br family home is 5 min to Woodstock&Barnard, town centers 20 min to the Killington skyeship, 35 min to Okemo an 5 min to S6. Its a Stunning Estate on 25 acres of lush Vermont. Woodstock is close and one of New England's favorites. Grill on the rear deck with your private hot tub. Sip wine on the porch with magical views. Make this your getaway. <2 hr to Boston. Inquire about Winter 24/25 leases.

Guest favourite

Villa in Bolton

4.94 out of 5 average rating, 64 reviews

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.

Villa in Rupert

4.31 out of 5 average rating, 58 reviews

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.

Guest favourite

Villa in Winhall

4.9 out of 5 average rating, 21 reviews

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.

Superhost

Villa in Brownsville

4.79 out of 5 average rating, 70 reviews

Villa with a Fireplace Near the Trails

Dreaming of a cozy villa with a fireplace? 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!

Superhost

Villa in Brownsville

4.8 out of 5 average rating, 10 reviews

Villa Near Biking and Hiking Trails

This villa is perfect for your group! 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!