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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor County villa rentals
Private villa rentals
Villa in Rutland
Pico D305 located slope side at Pico.
Jun 8 – 15
Villa in Killington
Sunrise Cambridge 101 located next to one of the b
Jul 21 – 28
Villa in Rutland
4.25 out of 5 average rating, 4 reviewsPico C103 located at the base of Pico Mountain
Mar 27 – Apr 3
Villa in Rutland
Pico F305 located slope side at Pico
Oct 31 – Nov 7
Villa in Killington
Sunrise Timberline I4
Sep 15 – 22
Luxury villa rentals
Villa in Killington
Sunrise Timberline K2 ski down to the Sunrise chai
Sep 8 – 15
Villa in Killington
Trail Creek 69
Feb 8 – 15
Villa in Rutland
Pico E202 with ski on/off at Pico Mountain
Dec 31 – Jan 7
Villa in Ludlow
4.94 out of 5 average rating, 32 reviewsModern 4 Bedroom 4 Bath Villa w HotTub/ back trail
Dec 16 – 23
Villa in Rutland
4.67 out of 5 average rating, 3 reviewsPico E205 located slope side at Pico
Dec 31 – Jan 7
Villa in Killington
4.64 out of 5 average rating, 11 reviewsTrail Creek 70, Fantastic 3 bed close to Mountain
Feb 16 – 23
Villa rentals with a pool
Villa in Killington
Whiffletree I1 has a shuttle & ski home trail
Oct 24 – 31
Villa in Killington
2.67 out of 5 average rating, 3 reviewsWhiffletree G1 Close to mountain biking and winter
Aug 1 – 8
Villa in Killington
Whiffletree I2 Take the shuttle to the mountain an
Jul 6 – 13
Villa in Brownsville
4.79 out of 5 average rating, 67 reviewsVilla with a Fireplace Near the Trails
May 26 – Jun 2
Villa in Brownsville
4.79 out of 5 average rating, 19 reviewsVilla with Pool + Fitness Center Access
Nov 22 – 29
Villa in Brownsville
4.8 out of 5 average rating, 10 reviewsVilla Near Biking and Hiking Trails
Jun 26 – Jul 3
Villa in Brownsville
Vermont Villa Near the Trails
Oct 26 – Nov 2
Villa in Killington
4.82 out of 5 average rating, 17 reviewsWhiffletree H1 newly renovated and on the shuttle
Jul 7 – 14
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- Rentals with breakfast Windsor County
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