Vacation rentals in Windsor County
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Windsor County
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor County vacation rentals
Other great vacation rentals in Windsor County
Guest favorite
Condo in Ludlow
4.92 out of 5 average rating, 123 reviewsOkemo Ski-in/Ski-out, Steps to lift Condo
Aug 26 – Sep 2
€ 124 per night
Guest favorite
Cabin in Royalton
4.99 out of 5 average rating, 174 reviewsGenuine Vermont Sugar House on 70 peaceful acres.
Jan 3 – 10
€ 165 per night
Guest favorite
Guest suite in West Windsor
4.9 out of 5 average rating, 103 reviewsNewly renovated private space on Ascutney Trails
Dec 14 – 21
€ 110 per night
Guest favorite
Condo in Ludlow
4.92 out of 5 average rating, 122 reviewsAll Season Lovely and Zen Okemo Mt Lodge Condo
May 19 – 26
€ 115 per night
Guest favorite
Townhouse in Killington
4.93 out of 5 average rating, 232 reviewsModern Mountain Condo with Spa, Pool, Sauna, Gym
May 13 – 20
€ 172 per night
Guest favorite
Guest suite in Royalton
4.96 out of 5 average rating, 180 reviewsPrivate Guest Suite on 155 Acre Royalton Town Farm
Jun 24 – Jul 1
€ 134 per night
Guest favorite
Guesthouse in Springfield
4.86 out of 5 average rating, 321 reviewsConnecticut River-Cozy Cottage
Apr 1 – 8
€ 98 per night
Guest favorite
Apartment in Chittenden
5.0 out of 5 average rating, 223 reviewsVermont Country Suite
Mar 6 – 13
€ 141 per night
Destinations to explore
- Rentals with pools Windsor County
- Farmstay rentals Windsor County
- Rentals with an EV charger Windsor County
- Cottage rentals Windsor County
- Family-friendly rentals Windsor County
- Private suite rentals Windsor County
- Rentals with a washer and dryer Windsor County
- Cabin rentals Windsor County
- Chalet rentals Windsor County
- Monthly Rentals Windsor County
- Bed and breakfasts Windsor County
- Rentals with a kayak Windsor County
- Rentals with an accessible height toilet Windsor County
- Rentals with breakfast Windsor County
- Rentals with outdoor seating Windsor County
- Kid-friendly rentals Windsor County
- Waterfront rentals Windsor County
- Guesthouse rentals Windsor County
- Villa rentals Windsor County
- Rentals with a sauna Windsor County
- Rentals with lake access Windsor County
- Rentals with a fire pit Windsor County
- Rentals with a hot tub Windsor County
- Townhouse rentals Windsor County
- Rentals with an accessible height bed Windsor County
- Condo rentals Windsor County
- Rentals with a patio Windsor County
- Fitness-friendly rentals Windsor County
- Apartment rentals Windsor County
- Tiny house rentals Windsor County
- Rentals with beach access Windsor County
- Pet-friendly rentals Windsor County
- Beachfront rentals Windsor County
- Rentals with a fireplace Windsor County
- House 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