227+ 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 227 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 1090.36 ft², with nightly prices averaging GB £279.

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 135
Holiday Apartments 26
Cottages 11

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, MA

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, MA

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


Jiminy Peak Mountain Resort
Tanglewood Music Center
Mass MoCA
Williams College
Berkshire East Ski Resort
Norman Rockwell Museum
National Shrine of the Divine Mercy
Mohawk Trail State Forest
Lee Prime Outlets
Bousquet Ski Area
Mount Greylock
Williamstown Theatre Festival
Cranwell Golf Club
Jacob's Pillow
Berkshire Museum
Bridge of Flowers
Hancock Shaker Village
Pittsfield State Forest
October Mountain State Forest
Beartown State Forest

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 holiday rentals have private pools in Windsor?

Discover a selection of holiday rentals with private pools near Windsor 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 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.uk holiday rentals are available in Windsor?

As of 2025, Casai boasts over 227 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 227 Windsor, MA Holiday Rentals

Recently Booked Holiday Rentals in Windsor