Windsor holiday rentals

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Scroll through and select from holiday rentals in Windsor to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for spending time at your holiday home, which might include a garden and hot tub. You're sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

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 has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Windsor

Are you hoping to find things to do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Windsor a fun place to get away to. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Montserrat Vineyards (16.9 mi / 27.3 km)
  • Shawnee Bend Public Use Area (19.5 mi / 31.4 km)
  • Bristle Ridge Vineyards (16.9 mi / 27.1 km)
  • Keth Memorial Golf Course at Pertle Springs (18.9 mi / 30.4 km)

Exploring the natural features in Windsor

Whether you're an adventurous traveller or just want to appreciate the scenery, Windsor is a great place to spend some time outside. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Truman Lake (19.2 mi / 31 km)
  • Truman Reservoir (19.7 mi / 31.6 km)
  • Truman Lake Mountain Bike Park (19.3 mi / 31 km)
  • Shawnee Bend Public Use Area (19.5 mi / 31.4 km)
  • Cave Hollow Park (21.1 mi / 33.9 km)
  • Vermont Park (19.5 mi / 31.3 km)

Transport to and around Windsor

The nearest airport is in Versailles, MO (VRS-Roy Otten Memorial Airfield), located 35.9 mi (57.8 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Windsor?
Property type, season and length of stay are some things that can affect the price of a holiday home. Simply add your travel dates to find your ideal match. From comfy cabins to sprawling luxury villas, all Stayz holiday homes provide unbeatable value.
How much does it cost to rent a beach house in Windsor?
Prices for beach houses in Windsor can vary depending on the type and size of the property and time of year you’re travelling. Simply enter your travel dates into Stayz and the number of guests to view your holiday home options and prices. From there you can use our filters to narrow your search results by ratings, nearby activities and more.
How old do you have to be to rent a holiday home in Windsor?
We recommend you check with the Windsor holiday property you’d like on Stayz as age restrictions differ. However, normally it’s 16, 18 or 21.
How long can I rent a holiday home in Windsor for?
The amount of time you can rent a Windsor holiday home for depends on the property. Just put in your preferred travel dates to find options that offer long-term stays. They include all you need to make your extended getaway more enjoyable and convenient, like laundries and air conditioning. Some holiday homes may also offer weekly or monthly discounted prices, so you can stick around for longer for less.