29+ Private Villas and Holiday Rentals in Windsor |
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Windsor Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Windsor

Discover more than 29 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 798.58 ft², with nightly prices averaging CA $247.

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 13
Holiday Apartments 2

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, CT

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, CT

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


Northwest Park
Windsor Arts Center
Vintage Radio and Communications Museum of Connecticut
Keney Park
SS&C SummerWind Performing Arts Center
Windsor Historical Society
Oliver Ellsworth Homestead
XL Center
Six Flags New England
Xfinity Theatre
University of Hartford
Naismith Memorial Basketball Hall of Fame
Connecticut Convention Center
MassMutual Center
Trinity College
Eastern States Exposition
Wesleyan University
MGM Springfield
Lake Compounce

Other Places to Stay in Windsor, CT


SS&C SummerWind Performing Arts Center 123 Properties
Keney Park 97 Properties
Poquonock 70 Properties
Northwest Park 69 Properties
Vintage Radio and Communications Museum of Connecticut 38 Properties
Oliver Ellsworth Homestead 35 Properties
Windsor Historical Society 34 Properties
Windsor Arts Center 34 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:

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

As of 2025, Casai boasts over 29 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 29 Windsor, CT Holiday Rentals

Recently Booked Holiday Rentals in Windsor