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Villa vacation rentals in Windsor County

Find and book unique villas on Airbnb

Top-rated villa rentals in Windsor County

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

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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 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!

Vacation rentals for every style

Get the amount of space that is right for you.

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Windsor County villa rentals

Free parking on premises

Air conditioning

Private villa rentals

Villa in Rutland

Pico D305 located slope side at Pico.

Villa in Rutland

4.25 out of 5 average rating, 4 reviews

Pico C103 located at the base of Pico Mountain

Villa in Rutland

Pico E202 with ski on/off at Pico Mountain

Villa in Rutland

Pico F305 located slope side at Pico

Villa in Killington

Trail Creek 69

Villa in Killington

Sunrise Timberline I4

Villa rentals with a pool

Villa in Killington

Sunrise Timberline K2 ski down to the Sunrise chai

Villa in Killington

5 out of 5 average rating, 3 reviews

Sunrise East Glade C8

Villa in Killington

4.67 out of 5 average rating, 3 reviews

Whiffletree B8 Great location with shuttle bus to

Villa in Brownsville

4.8 out of 5 average rating, 20 reviews

Villa with Pool + Fitness Center Access

Villa in Killington

4.56 out of 5 average rating, 9 reviews

Whiffletree C2 has been totally renovated and look

Villa in Killington

Whiffletree I2 Take the shuttle to the mountain an

Villa in Killington

4.64 out of 5 average rating, 11 reviews

Trail Creek 70, Fantastic 3 bed close to Mountain

Villa in Killington

2.67 out of 5 average rating, 3 reviews

Whiffletree G1 Close to mountain biking and winter

Villa rentals with a hot tub

Villa in Killington

4 out of 5 average rating, 4 reviews

Woods Resort and Spa Village 34

Villa in Killington

Sunrise Timberline G2 ski down to the Sunrise chai

Villa in Killington

Sunrise West Glade K1

Villa in Killington

4.33 out of 5 average rating, 3 reviews

Sunrise Timberline I7

Villa in Killington

Trail Creek 52 on the Shuttle with ski back trail

Villa in Killington

Trail Creek 57 with ski back trail

Destinations to explore