Winchester Vacation Rentals

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 24 - Oct 26
In two months
Dec 5 - Dec 7
In three months
Jan 2 - Jan 4
In four months
Jan 30 - Feb 1

Vacation Rentals in Winchester

White House at Grand Central
1 bedroom, individually decorated, individually furnished, desk

White House at Grand Central

4.0 star property
8.4 out of 10, Very Good, (120)
"The property is in a Safe neighborhood. "
White House at Grand Central
Landing Downtown St. Louis
Property amenity

Landing Downtown St. Louis

4.0 star property
7.6 out of 10, Good, (15)
"Great place to stay when watching the Cardinals. "
Landing Downtown St. Louis
DreamAwayHome Metro
Living room

DreamAwayHome Metro

2.0 star property
2.0 out of 10, (1)
"I sisnt like rhat the property was dirty when i arrived and still had to pay cleaning fees. Also the shower and bath wasnt readhcto be used so i had to ojt the unit into a nother unit to shower/bath"
DreamAwayHome Metro
Quaint St Louis Home ~ 6 Mi to Downtown!
Interior

Quaint St Louis Home ~ 6 Mi to Downtown!

3.0 star property
Quaint St Louis Home ~ 6 Mi to Downtown!
Value Suites Extended Stay - St Louis
1 bedroom, desk, laptop workspace, blackout drapes

Value Suites Extended Stay - St Louis

3.0 star property
7.0 out of 10, Good, (1110)
"Close to the city, very comfortable and has a full kitchen which is nice."
The price is P19,909
P27,836 total
includes taxes & fees
Oct 7 - Oct 8
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

Drury Inn & Suites St. Louis Union Station

Drury Inn & Suites St. Louis Union Station

10/10 Excellent
"The hotel was fabulous. Cheerful and helpful staff. Great amenities and convenient to many area attractions. I would highly recommend and would love to stay again if visiting St. Louis. Parking was safe and reasonably priced for a downtown location. Room was relaxing and clean. "
Rayanne 2-night trip
Posted 2 days ago
Drury Inn & Suites St. Louis Union Station

Find out more about Winchester

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 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 The Factory.

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.