1995+ Rental Villas and Private Getaways in Windsor County |
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Windsor County Villa Rentals

About Windsor County Vacation Rentals

There are more than 1995 incredible getaway rentals that are available in Windsor County. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Windsor County.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Windsor County, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Windsor County. Places to stay near Windsor County are 1131.17 ft² on average, with prices averaging US $542 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Windsor County. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Private Villas, Resorts, and Rentals in Windsor County

Type Count
Vacation Homes 998
Holiday Apartments 185
Cabin Rentals 107
Ski Chalet Rentals 55
Others 37
Cottages 36
B&B 26
Villas 6
Unique Vacation Rentals 4

Use these Quick Filters to Find a Vacation Rental in Windsor County

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Windsor County with BedroomVillas.

Weather in Windsor County, VT

View the weather forecast for Windsor County before booking your Windsor County Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Windsor County's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Windsor County's Research Top Attractions For Your Vacation


Okemo Mountain Resort
Quechee Gorge
Jackson Gore Ski Resort at Okemo
King Arthur Flour
Quechee Gorge Village
Little Pico Mountain
Weston Playhouse
Suicide Six Ski Area
Weston Priory
Mt Ascutney State Park
Upper Valley Aquatic Center
Sugarbush Farm
Simon Pearce Mill
Mount Ascutney
Woodstock Country Club
Billings Farm and Museum
Okemo Valley Golf Club
Silver Lake State Park
Vermont River Tubing
Woodstock Town Hall Theatre
Briggs Opera House
Montshire Museum of Science
Wilderness Trails
Buttermilk Falls
Long Trail Brewing Company
Calvin Coolidge Historic Site
Mount Tom Peak
Vermont Institiute of Natural Science
Calvin Coolidge Homestead
Harpoon Brewery

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Ludlow 832 Properties
Bridgewater Corners 146 Properties
West Bridgewater 112 Properties
Cavendish 101 Properties
Woodstock 99 Properties
Quechee 90 Properties
Chester 78 Properties
Chester Depot 78 Properties
Plymouth 71 Properties
Proctorsville 55 Properties
Weston 47 Properties
Andover 36 Properties

Complexes around Windsor County, VT


Cedarbrook 29 Properties
Winterplace Ludlow 22 Properties
Located 20 Properties
Okemo Mountain Lodge 13 Properties
Efficiency Sofa 8 Properties
Kettle Brook 8 Properties
Hotel 6 Properties
Br Of Ski Lift 4 Properties
Ghia Farm Road 4 Properties
Comfort Inn White River Junction 3 Properties
Hampton Inn White River Junction 3 Properties
Holiday Inn Club Vacations Mount Ascutney Resort Ihg Hotel 3 Properties
Holiday Inn Express Hotel White River Junction Ihg 3 Properties
Hotel Coolidge 3 Properties
Mountain Lodge At Renovated 3 Properties
See More Complexes

Frequently Asked Questions About Windsor County?

What are the top hotels or resorts in Windsor County?

We provide an array of great vacation destinations in Windsor County. If you are looking to stay in or around the Windsor County area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Windsor County:

How many vacation rentals have private pools in Windsor County?

We have 60 luxury villas and vacation rentals featuriung a private pool in and near Windsor County. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel or resort in Windsor County is best for families?

Searching for a family-friendly getaway in Windsor County? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Windsor County?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2025 is over 1995 in the Windsor County area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Windsor County. 


People Also Ask

There are 140 hotels in Windsor County 18 resorts, and 1296 rentals

Recently Booked Hotels, Resorts, or Rentals in Windsor County