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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Winchester holiday rentals

Studio Suite, 1 King Bed | Desk, laptop workspace, blackout curtains, WiFi

Value Suites Extended Stay - St Louis

Value Suites Extended Stay - St Louis
3.0 star property
Maryland Heights
7.0 out of 10, Good, (1,110 reviews)
"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 10.624.538 ₫
14.478.114 ₫ total
includes taxes & fees
23 Mar - 24 Mar
Value Suites Extended Stay - St Louis
Lobby

White House at Grand Central

White House at Grand Central
4.0 star property
Grand Center
8.4 out of 10, Very good, (130 reviews)
"Very clean and very friendly people "
United States
Mary
The price is 2.252.185 ₫
3.553.468 ₫ total
includes taxes & fees
18 Mar - 19 Mar
White House at Grand Central
Apartment (2 Bedrooms) | Interior

Walk to Bars & Dining: Historic Benton Park Gem

Walk to Bars & Dining: Historic Benton Park Gem
3.0 star property
Benton Park
The price is 2.576.028 ₫
8.811.593 ₫ total
includes taxes & fees
30 Mar - 31 Mar
Walk to Bars & Dining: Historic Benton Park Gem
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 9.121.242 ₫
22.671.793 ₫ total
includes taxes & fees
1 Apr - 2 Apr
3323: Uptown Elegant Escape 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 6.730.517 ₫
21.763.637 ₫ total
includes taxes & fees
1 Apr - 2 Apr
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.
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Top Winchester Hotel Reviews

Clayton Plaza Hotel & Extended Stay

Clayton Plaza Hotel & Extended Stay

6/10 Okay
"Friendly staff at breakfast. The hotel rooms are ok, the bathrooms are nice and updated, but the floors in the rooms need to mopped properly as they feel quite sticky and dirty. Good that it has a gym, but there’s a mismatch of single weights of varying size. The use of plastic wrapped plastic cutlery at breakfast is not great, would be great if that was changed into something more environmentally friendly."
Martti 2-night trip
Posted 3 hours ago
Clayton Plaza Hotel & Extended Stay

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select 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 wider area, you’ll find Museum of Transportation and The Factory.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.