2091+ Private Villas and Holiday Rentals in Windsor County |
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  3. Windsor County

Windsor County Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Windsor County

Discover more than 2091 vacation rentals available in Windsor County. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windsor County.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windsor County, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windsor County. On average, places to stay near Windsor County offer 1120.16 ft², with nightly prices averaging US $571.

With Casai, finding and comparing holiday rentals in Windsor County is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Windsor County

Type Count
Vacation Homes 1049
Holiday Apartments 187
Cottages 40
Villas 6

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

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Windsor County.

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

Top Attractions Around Windsor County, VT

Casai offers a large selection of top attractions around Windsor County . Research things to do on your vacation before you visit Windsor County.


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

Other Places to Stay in Windsor County, VT


Ludlow 706 Properties
Bridgewater Corners 122 Properties
West Bridgewater 91 Properties
Cavendish 82 Properties
Woodstock 70 Properties
Quechee 61 Properties
Plymouth 59 Properties
Chester 58 Properties
Chester Depot 58 Properties
Proctorsville 44 Properties
Weston 35 Properties
West Windsor 27 Properties

Frequently Asked Questions About Windsor County?

What are the top holiday rentals in Windsor County?

With numerous options available in Windsor County, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Windsor County:

How many holiday rentals have private pools in Windsor County?

Discover a selection of holiday rentals with private pools near Windsor County with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Windsor County are best for families?

If you're searching for a family-friendly holiday home in Windsor County, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Windsor County:

How many Casai.nz holiday rentals are available in Windsor County?

As of 2026, Casai boasts over 2091 properties listed in the Windsor County area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windsor County.


People Also Ask

There are 2091 Windsor County, VT Holiday Rentals

Recently Booked Holiday Rentals in Windsor County