57+ Private Villas and Holiday Rentals in Windsor |
  1. USA
  2. Vermont
  3. Central Vermont- Killington
  4. Windsor

Windsor Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Windsor

Discover more than 57 vacation rentals available in Windsor. 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.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windsor, 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. On average, places to stay near Windsor offer 994.61 ft², with nightly prices averaging US $471.

With Casai, finding and comparing holiday rentals in Windsor 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

Type Count
Vacation Homes 21
Villas 5
Cottages 2
Holiday Apartments 1

Use these Quick Filters to Find a Holiday Rental in Windsor

★ 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.

Weather in Windsor, VT

View the weather forecast for Windsor before booking your Windsor 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, VT

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


Mt Ascutney State Park
Mount Ascutney
Harpoon Brewery
Paradise Park
South Congregational Church
American Precision Museum
The Sustainable Farmer
Brownsville Trail
Path of Life Garden
Old Constitution House
Mt Ascutney Hospital and Health Center: Primary Care - Windsor
Killington Resort
Okemo Mountain Resort
Dartmouth College
Killington Peak
Pico Mountain at Killington Ski Resort
Dartmouth-Hitchcock Medical Center
Quechee Gorge
Lake Sunapee
Mount Sunapee

Other Places to Stay in Windsor, VT


Harpoon Brewery 90 Properties
Path of Life Garden 89 Properties
Brownsville Trail 87 Properties
Ascutney 87 Properties
Paradise Park 80 Properties
Mt Ascutney Hospital and Health Center: Primary Care - Windsor 79 Properties
The Sustainable Farmer 79 Properties
Old Constitution House 79 Properties
South Congregational Church 79 Properties
American Precision Museum 79 Properties
Mount Ascutney 55 Properties
Mt Ascutney State Park 53 Properties

Frequently Asked Questions About Windsor?

What are the top holiday rentals in Windsor?

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

Which holiday homes in Windsor are best for families?

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

How many Casai.com holiday rentals are available in Windsor?

As of 2025, Casai boasts over 57 properties listed in the Windsor area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windsor.


People Also Ask

There are 57 Windsor, VT Holiday Rentals

Recently Booked Holiday Rentals in Windsor