Villa holiday rentals in Rutland

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

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.

2-Bedroom Villa w/ King, Queen & Private Balcony

Set among the forested hills of southern Vermont, this two-bedroom villa is the perfect mountain escape for families and small groups. A fully equipped kitchen, dedicated dining area, and a private balcony invite you to unwind after a day in the Green Mountains. On-site amenities include a fitness center, movie theater, game room, and outdoor fire pits — everything you need for a memorable Vermont getaway.

The Upper Valley Retreat

Upper Valley Retreat: A 20-Acre Vermont Symphony of Light, Land, and Legacy Tucked into the gentle embrace of the Upper Valley, where rolling meadows meet the ancient hush of Brushwood Forest, stands the Upper Valley Retreat — a magnificent 20-acre estate and working apple orchard that feels like a poem written in wood, stone, and sky.

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!

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 Games Room + 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!

Whiffletree Out Door, Pool, Tennis, Golf

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

Base of Killington with Sports center, golf

Trail Creek 12, Lovely 1 bedroom close to Mountain

Base of Killington with Sports center access Golf

Trail Creek 52 on the Shuttle with ski back trail

Base of Killington with Sports center access Golf

Trail Creek 70, Fantastic 3 bed close to Mountain

Base of Killington with Sports center access Golf

Trail Creek, Lovely 2 bedroom close to Mountain