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Villa holiday 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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Guest favourite

Private room in Windsor

4.9 out of 5 average rating, 39 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

Guest favourite

Villa in Ludlow

4.93 out of 5 average rating, 44 reviews

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail

This unique house has a style all its own. with floor to ceiling windows and doors throughout There are 3 levels. top floor has 2 bedrooms with full baths and Hot Tub on the balcony middle level entry; plus Great room: with kitchen, dining, living, activity area with a big table, fireplace and 75 inch television bottom level has 2 bedrooms and 2 full baths

Villa in Brownsville

4.79 out of 5 average rating, 71 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!

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!

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Popular amenities for villa rentals in Windsor County

Free parking on premises

Air conditioning

Private villa rentals

Villa in Killington

Trail Creek 11 is on a ski home trail

Villa in Rutland

5 out of 5 average rating, 3 reviews

Pico D305 located slope side at Pico quiet area

Villa in Killington

5 out of 5 average rating, 3 reviews

Sunrise East Glade C8

Villa in Brownsville

4.83 out of 5 average rating, 23 reviews

Villa with Pool + Fitness Center Access

Villa in Killington

4.64 out of 5 average rating, 11 reviews

Base of Killington with Sports center access

Villa in Killington

Sunrise Timberline I4

Guest favourite

Villa in Ludlow

4.93 out of 5 average rating, 44 reviews

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail

Villa in Brownsville

4.67 out of 5 average rating, 3 reviews

Vermont Villa Near the Trails

Villa rentals with a pool

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

4.83 out of 5 average rating, 23 reviews

Villa with Pool + Fitness Center Access

Villa in Killington

4.33 out of 5 average rating, 3 reviews

Sunrise Timberline I7

Villa in Killington

4.56 out of 5 average rating, 9 reviews

Whiffletree base of Killington outdoor pool

Villa in Killington

Whiffletree base of Killington outdoor pool

Villa in Killington

4.64 out of 5 average rating, 11 reviews

Base of Killington with Sports center access

Villa in Killington

2.67 out of 5 average rating, 3 reviews

Whiffletree base of Killington outdoor pool

Villa rentals with a hot tub

Villa in Killington

4.33 out of 5 average rating, 3 reviews

Sunrise Timberline I7

Villa in Killington

Base of Killington with Sports center access

Villa in Killington

Base of Killington with Sports center access

Villa in Killington

Base of Killington with Sports center access

Destinations to explore