Winchester Holidays

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Your Winchester Holiday

Book a Winchester holiday package and get set to experience the best of this lively city. Consider basing yourself in the neighbourhood of Maplewood, which is good for bars and pubs, gift and craft shops and dining. Searching for some sightseeing inspiration for your trip to Winchester? Castlewood State Park and American Kennel Club Museum of the Dog are two must-visit attractions here. Whoever you're travelling with and whatever the size of your budget, your dream Winchester holiday is just clicks away with Expedia.

Winchester Holiday

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lambert-St. Louis Intl. Airport (STL)
Population
1,550
Max Temp Winter
4ºC
Max Temp Summer
32ºC

Our pick of the best Winchester Hotel Deals

Drury Plaza Hotel St. Louis at the Arch

Drury Plaza Hotel St. Louis at the Arch

3 out of 5
2 South 4th Street, St. Louis, MO
Fully refundableReserve now, pay when you stay
The price is AU$259 per night from 26 Oct to 27 Oct
AU$259
26 Oct - 27 Oct
includes taxes & fees
9.4/10 Exceptional! (3,175 reviews)
"Everything about my stay was good. It was a little strange to have the window in my room overlooking the inside courtyard of the hotel but it was still a pleasant stay. The evening and morning buffet was substantial and good."

Reviewed on 18 Oct 2025

Drury Plaza Hotel St. Louis at the Arch
Clayton Plaza Hotel & Extended Stay

Clayton Plaza Hotel & Extended Stay

3.5 out of 5
7750 Carondelet Avenue, St. Louis, MO
Fully refundableReserve now, pay when you stay
The price is AU$188 per night from 2 Nov to 3 Nov
AU$188
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (2,996 reviews)
"Was a good place for us to stay. Room was nice, only shared breakfast one time. Parking Ramp easy and convenient."

Reviewed on 18 Oct 2025

Clayton Plaza Hotel & Extended Stay
Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

4 out of 5
315 Chestnut St, St. Louis, MO
Fully refundableReserve now, pay when you stay
The price is AU$221 per night from 2 Nov to 3 Nov
AU$221
2 Nov - 3 Nov
includes taxes & fees
8.4/10 Very Good! (4,022 reviews)
Lovely hotel, buy parking could be better
"Came here for Galaxycon. Great location with the Arch just across the street. Parking was hit and miss though. For some reason you have to tell someone when you check in that you want to self-park otherwise using your room key to leave and come back doesn't work. Plus their parking garage can fill ..."

Reviewed on 18 Oct 2025

Hyatt Regency St. Louis at The Arch
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.