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

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

4 out of 5
421 N 8th St St. Louis MO
Fully refundableReserve now, pay when you stay
The price is AU$182 per night from 8 Dec to 9 Dec
AU$182
8 Dec - 9 Dec
includes taxes & fees
8.6/10 Excellent! (1,135 reviews)
Beautiful Hotel! Comfortable rooms and friendly staff.

Reviewed on 28 Nov 2025

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel
Pear Tree Inn St. Louis Airport

Pear Tree Inn St. Louis Airport

2.5 out of 5
10810 Pear Tree Ln St. Ann MO
Fully refundableReserve now, pay when you stay
The price is AU$160 per night from 9 Dec to 10 Dec
AU$160
9 Dec - 10 Dec
includes taxes & fees
9.2/10 Wonderful! (2,754 reviews)
Was a very nice stay! Bandanas next door is so good!!

Reviewed on 29 Nov 2025

Pear Tree Inn St. Louis Airport
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$169 per night from 21 Dec to 22 Dec
AU$169
21 Dec - 22 Dec
includes taxes & fees
8.4/10 Very Good! (3,995 reviews)
Couldn't adjust the heat in my room as it was below freezing outside. Also, they misinformed me about the garage parking. Made my 1$t few trips inside & outta the hotel very stressful.....

Reviewed on 4 Dec 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.