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 Killington
Sunrise Cambridge 101 located next to one of the b
Aug 31 – Sep 7
Villa in Rutland
Pico D305 located slope side at Pico.
Apr 12 – 19
Villa in Rutland
4.25 out of 5 average rating, 4 reviewsPico C103 located at the base of Pico Mountain
Mar 31 – Apr 7
Villa in Rutland
Pico F305 located slope side at Pico
Nov 4 – 11
Luxury villa rentals
Villa in Rutland
Pico E202 with ski on/off at Pico Mountain
Jan 4 – 11
Villa in Killington
Sunrise Timberline K2 ski down to the Sunrise chai
Sep 12 – 19
Villa in Killington
Trail Creek 69
Feb 12 – 19
Villa in Killington
Sunrise Timberline I4
Apr 17 – 24
Villa rentals with a pool
Villa in Killington
Whiffletree I1 has a shuttle & ski home trail
Apr 11 – 18
Villa in Killington
2.67 out of 5 average rating, 3 reviewsWhiffletree G1 Close to mountain biking and winter
Feb 12 – 19
Villa in Killington
Whiffletree I2 Take the shuttle to the mountain an
Dec 7 – 14
Villa in Brownsville
4.79 out of 5 average rating, 19 reviewsVilla with Pool + Fitness Center Access
Jan 11 – 18
Villa in Brownsville
4.79 out of 5 average rating, 67 reviewsVilla with a Fireplace Near the Trails
Jul 2 – 9
Villa in Brownsville
4.8 out of 5 average rating, 10 reviewsVilla Near Biking and Hiking Trails
May 31 – Jun 7
Villa in Brownsville
Vermont Villa Near the Trails
Aug 16 – 23
Villa in Killington
4.82 out of 5 average rating, 17 reviewsWhiffletree H1 newly renovated and on the shuttle
Dec 27 – Jan 3
Destinations to explore
- Villa rentals United States
- Villa rentals Vermont
- Villa rentals Vermont
- Villa rentals New York
- Villa rentals New Hampshire
- Apartment rentals Windsor County
- Bed and breakfasts Windsor County
- Rentals with pools Windsor County
- Rentals with lake access Windsor County
- Pet-friendly rentals Windsor County
- Condo rentals Windsor County
- Rentals with a washer and dryer Windsor County
- Cabin rentals Windsor County
- Chalet rentals Windsor County
- Rentals with a hot tub Windsor County
- Cottage rentals Windsor County
- Ski-in/ski-out rentals Windsor County
- Rentals with outdoor seating Windsor County
- Tiny house rentals Windsor County
- Rentals with a sauna Windsor County
- Rentals with a patio Windsor County
- Farmstay rentals Windsor County
- Rentals with an EV charger Windsor County
- Rentals with a fire pit Windsor County
- Kid-friendly rentals Windsor County
- Guesthouse rentals Windsor County
- House rentals Windsor County
- Private suite rentals Windsor County
- Family-friendly rentals Windsor County
- Townhouse rentals Windsor County
- Rentals with breakfast Windsor County
- Rentals with a kayak Windsor County
- Waterfront rentals Windsor County
- Beachfront rentals Windsor County
- Rentals with an accessible height bed Windsor County
- Rentals with an accessible height toilet Windsor County
- Rentals with a fireplace Windsor County
- Monthly Rentals Windsor County
- Rentals with beach access Windsor County
- Fitness-friendly rentals Windsor County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom