Winchester Vacation Rentals

  • 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

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Winchester vacation rentals

Interior

3323: Uptown Elegant Escape by JZ Vacation Rentals

3323: Uptown Elegant Escape by JZ Vacation Rentals
2.0 star property
The Gate
The price is ₩508,147
₩1,263,053 total
includes taxes & fees
Mar 15 - Mar 16
3323: Uptown Elegant Escape by JZ Vacation Rentals
House, Multiple Beds, Kitchen, City View (508 Trudy Ln) | 3 bedrooms, individually decorated, individually furnished, bed sheets

The Secret Sojourn | JZ Vacation Rentals

The Secret Sojourn | JZ Vacation Rentals
3.0 star property
O'Fallon
The price is ₩262,450
₩808,738 total
includes taxes & fees
Mar 18 - Mar 19
The Secret Sojourn | JZ Vacation Rentals
Lobby

White House at Grand Central

White House at Grand Central
4.0 star property
Grand Center
8.4 out of 10, Very Good, (128 reviews)
"Very clean and very friendly people "
United States
Mary
The price is ₩125,470
₩197,964 total
includes taxes & fees
Mar 24 - Mar 25
White House at Grand Central
House (3 Bedrooms) | Interior

508: The Secret Sojourn by JZ Vacation Rentals

508: The Secret Sojourn by JZ Vacation Rentals
2.5 star property
O'Fallon
The price is ₩366,100
₩843,963 total
includes taxes & fees
Mar 18 - Mar 19
508: The Secret Sojourn by JZ Vacation Rentals
House, Multiple Beds, Patio, City View ((#19) 3323 Vista Ave) | Private kitchen

Uptown Elegant Escape | JZ Vacation Rentals

Uptown Elegant Escape | JZ Vacation Rentals
2.0 star property
The Gate
The price is ₩374,930
₩1,212,367 total
includes taxes & fees
Mar 15 - Mar 16
Uptown Elegant Escape | JZ Vacation Rentals
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

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

6/10 Okay
"Very poor water pressure in the shower, sink didn’t drain nicely, and hotel is dated. "
Jody Charles 3-night trip
Posted 2 hours ago
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

Find out more about Winchester

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

  • View our selection of featured Vacation rentals in Winchester
  • Use the map to find apartments and other Vacation homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation 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 Bellerive Country Club 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.