Winchester Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 22 - Dec 23
Tomorrow
Dec 23 - Dec 24
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Winchester vacation rentals

Comfort Apartment | Individually decorated, individually furnished, desk, laptop workspace
White House at Grand Central

Apartment in Grand Center

White House at Grand Central
4.0 star property
8.6 out of 10, Excellent, (124)
"Very clean and very friendly people "
United States
Mary
The price is ￥10,257
￥22,140 total
includes taxes & fees
Jan 19 - Jan 20, 2026
White House at Grand Central
Studio Suite, 1 King Bed | Desk, laptop workspace, blackout drapes, WiFi
Value Suites Extended Stay - St Louis

Aparthotel in Maryland Heights

Value Suites Extended Stay - St Louis
3.0 star property
7.0 out of 10, Good, (1110)
"We’ve stayed here twice before and have always been pleased with everything. Very good hotel close to what we need."
United States
Timothy
The price is ￥60,301
￥82,873 total
includes taxes & fees
Dec 23 - Dec 24
Value Suites Extended Stay - St Louis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Home2 Suites by Hilton St. Louis Downtown

Home2 Suites by Hilton St. Louis Downtown

10/10 Excellent
"Great stay which is consistent for the Home 2 Suites. "
Jennifer 1-night trip
Posted 1 day ago
Home2 Suites by Hilton St. Louis Downtown

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals close to the most popular local attractions in Winchester, or you can go with a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Winchester?

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!: This vacation home rental outside of Winchester is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like Magic House - St. Louis Children's Museum, or get outside and enjoy nature at Lou Fusz Soccer Complex. In the larger area, you’ll find Museum of Transportation and Bellerive Country Club.

What’s a vacation rental in Winchester like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Winchester. Vacation rentals offer amenities such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.