Winchester holiday rentals

We found 103 holiday rentals — enter your dates for availability
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.

Holiday rentals with weekly discounts – Winchester

Showing deals for:13 Nov - 20 Nov

Terrace/patio
Private kitchen
Interior
Exterior
Very good
(24 reviews)

Office and 5 BR, Updated Bathrooms, Movie Theater in Creve Coeur

St. Louis

20% off
AU$4,447
for 7 nights, 1 home
AU$635 per night
includes taxes & fees
Office and 5 BR, Updated Bathrooms, Movie Theater in Creve Coeur
Exterior detail
Private kitchen
Living area
Dining
Exceptional
(13 reviews)

Pet and Family Friendly House - Great Location- 30 Minutes to Downtown

Ballwin

8% off
AU$3,857
for 7 nights, 1 home
AU$551 per night
includes taxes & fees
Pet and Family Friendly House - Great Location- 30 Minutes to Downtown
Interior
Living area
Interior
Room
Exceptional
(5 reviews)

Spacious 4BR Family Home Near Historic St. Charles & STL

St. Charles

8% off
AU$2,518
for 7 nights, 1 home
AU$360 per night
includes taxes & fees
Spacious 4BR Family Home Near Historic St. Charles & STL
Interior
This family lives in the back yard, just steps away from the pool suite.
Private indoor pool suite (Heated but NOT air conditioned) w/child safety alarm
Many floral trees and bulbs are in full bloom in the Spring..
Exceptional
(256 reviews)

Retro Ranch With Private Indoor Pool & Sauna St Louis, MO

Ballwin

7% off
AU$5,216
for 7 nights, 1 home
AU$745 per night
includes taxes & fees
Retro Ranch With Private Indoor Pool & Sauna St Louis, MO
Exterior detail
Pool
Private kitchen
Outdoor dining
Exceptional
(6 reviews)

Fenton Oasis - private pool and garden

Fenton

8% off
AU$4,402
for 7 nights, 1 home
AU$629 per night
includes taxes & fees
Fenton Oasis - private pool and garden
Exterior
Private kitchen
Room
Living area
Excellent
(57 reviews)

3-bedroom vacation home just 20 minutes from Six Flags St. Louis

Ballwin

8% off
AU$2,173
for 7 nights, 1 home
AU$310 per night
includes taxes & fees
3-bedroom vacation home just 20 minutes from Six Flags St. Louis
  • 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)
  • 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)
  • Creve Coeur Golf Club (7.3 mi / 11.8 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)
  • 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)
  • Jefferson Barracks Historic Park (14.5 mi / 23.3 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 Stayz 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 Stayz, 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 Stayz'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.