Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Find vacation rentals that suit your style

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Apartments
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Condos
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Top Windsor Hotel Reviews

A hotel room with a large bed, a separate desk with a chair, a TV, a bathroom with a bathtub, and a window with curtains.
Comfort Suites Mattoon East

Comfort Suites Mattoon East

Comfort Suites Mattoon East
Mattoon

10/10 Excellent

U r consistent
United States
Bernard
Reviewed November 7, 2026
Comfort Suites Mattoon East

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently Asked Questions

Are there vacation rentals in Windsor?

Yes, we have vacation rentals close to the most popular sights in Windsor, or you can choose a more remote option if you're looking for relaxation. Windsor is known for its restaurants and shopping.

What can I see and do in Windsor?

While you're exploring the area, Lake Shelbyville and Lake Shelbyville Beach are a couple of picturesque spots to get outside and enjoy nature. Mattoon City Hall and Wolf Creek State Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can book for a couple days or more in Windsor. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for small groups.