Windsor holiday homes

We found 12 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Windsor to find one that's perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Windsor getaway

Learn about the unique charm of Windsor with a stay in a holiday home rental. This city is well-known for its restaurants and shopping. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Exploring the natural landscape of Windsor

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Windsor is a great spot to appreciate mother nature. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Lake Shelbyville (7.8 mi / 12.6 km)
  • Lake Shelbyville Beach (10.1 mi / 16.2 km)
  • Mattoon Peterson Park (13.1 mi / 21 km)
  • Forest Park (10.3 mi / 16.6 km)

Transport options to and around Windsor

The nearest airport is in Decatur, IL (DEC), located 31 mi (49.9 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Windsor?
Property type, length of stay and season are some factors that can influence the price of a holiday home. Simply enter your travel dates to find the ultimate escape. From comfy cabins to expansive luxury villas, all Bookabach holiday homes offer amazing value.
How much does it cost to rent a beach house in Windsor?
When you travel and the style and size of the property will help determine the cost of your beachside stay. Type in your Windsor travel dates to see your options on Bookabach. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to select the features and amenities you want.
What are the top attractions for families in Windsor?
There are lots of exciting things to do and see with the family in Windsor, such as:

  • Lake Shelbyville
  • Wolf Creek State Park
  • Eagle Creek State Park

How old do you have to be to rent a holiday home in Windsor?
The minimum age is typically 16, 18 or 21. It can differ from one property to another on Bookabach, so look at the rules of your preferred Windsor holiday home before you book.
How long can I rent a holiday home in Windsor for?
How long you can book a holiday home in Windsor is up to the property. Just enter your selected travel dates to look at a list of options offering extended stays. With tons of creature comforts like washing machines and kitchens, as well as some offering weekly or monthly discounts, you're sure to get somewhere perfect to call your home away from home in Windsor.

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