Search Holiday Rentals in Winchester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Top Holiday Rentals in Winchester

Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, we have holiday rentals where you'll be just 13.2 mi (21.2 km) from St. Louis Zoo, providing a more secluded option if you want peace and quiet.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like St. Louis Zoo, or get outside and enjoy nature at Lone Elk Park. In the wider area, you’ll find Museum of Transportation and The Factory.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.