Winchester holiday homes, MO, USA: holiday houses & more

Scroll through and select from holiday rentals in Winchester to find one that's perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the amenities that you expect and more, which might include Wi-Fi and a hot tub. At the end of the day, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Winchester

Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues

Sleeps 4 · 3 bedrooms · 1 bathroom

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

Book a holiday rental for your Winchester getaway

Learn about the unique charm of Winchester with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Winchester

Are you hoping to find things to do in the city? Venture out of your cosy holiday rental and experience everything that makes Winchester a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

St. Louis Zoo (13.2 mi / 21.2 km)
Chesterfield Sports Fusion (7.1 mi / 11.4 km)
Hidden Valley Ski Resort (7.8 mi / 12.5 km)
Six Flags St. Louis (9.5 mi / 15.3 km)
Grant's Farm (9.8 mi / 15.8 km)
Chandler Hill Vineyards (15.1 mi / 24.3 km)

Exploring the natural landscape of Winchester

Whether you're looking for fun outdoor activities or just want to take in the scenery, Winchester is a great place to get out in nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

Lou Fusz Soccer Complex (7.7 mi / 12.4 km)
Lindenwood Park (12.1 mi / 19.4 km)
Jewel Box (13.7 mi / 22.1 km)
Forest Park (13.9 mi / 22.4 km)
Tower Grove Park (14.2 mi / 22.8 km)
Katy Trail (14.3 mi / 23 km)

Travelling to and around Winchester

The nearest airport is in St. Louis, MO (SUS-Spirit of St. Louis), located 8.1 mi (13 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Lambert-St. Louis International Airport (STL), which is 13.7 mi (22 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Winchester?

The average price for a holiday home in Winchester is determined by a number of factors, like season, property type and length of stay. Whether you prefer a sprawling house with room for friends and family or a quaint cottage just enough for two, just enter your dates of travel to see some great-value stays.

How much does it cost to rent a beach house in Winchester?

Prices for beach houses in Winchester may vary depending on the type and size of the property and when you’re travelling. Simply enter your dates of travel into Bookabach and the number of guests to view holiday home options and prices. From there you can use our filter tool to narrow your search results by amenities, ratings, nearby activities and more.

How old do you have to be to rent a holiday home in Winchester?

Age restrictions can vary across properties on Bookabach, so double-check the rules of the holiday home in Winchester you’re considering. But usually, it’s 16, 18 or 21.

How long can I rent a holiday home in Winchester for?

It’s up to the Winchester property. To browse a list of options offering extended stays, just enter your dates and guest number into Bookabach’s search page. You can look forward to having the whole place to yourself, as well as comforts such as air conditioning, a fully-equipped kitchen and a backyard where the kids can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.