Book Hotels in Winchester, MO

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Top Winchester hotels

Drury Plaza Hotel St. Louis Union Station

Drury Plaza Hotel St. Louis Union Station

3 out of 5
201 S 20th St St. Louis MO
Fully refundableReserve now, pay when you stay
The price is $134 total per night from Nov 15 to Nov 16
$134 total
per night
Nov 15 - Nov 16
This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
"Awesome location! We were able to walk to Union Station attractions as well as The Enterprise Center. The dinner and breakfast buffets are top notch!"

Reviewed on Oct 31, 2026

Opens in a new windowDrury Plaza Hotel St. Louis Union Station
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 $104 total per night from Nov 8 to Nov 9
$104 total
per night
Nov 8 - Nov 9
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport ...
Opens in a new windowPear Tree Inn St. Louis Airport
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 $168 total per night from Nov 9 to Nov 10
$168 total
per night
Nov 9 - Nov 10
2 hot tubs, an indoor pool, and a gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in ...
Opens in a new windowDrury Plaza Hotel St. Louis at the Arch
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 $148 total per night from Nov 25 to Nov 26
$148 total
per night
Nov 25 - Nov 26
This smoke-free hotel's 3 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business ...
Opens in a new windowHyatt Regency 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 $128 total per night from Nov 22 to Nov 23
$128 total
per night
Nov 22 - Nov 23
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy ...
Opens in a new windowClayton Plaza Hotel & Extended Stay
Hollywood Casino & Hotel St. Louis

Hollywood Casino & Hotel St. Louis

3.5 out of 5
777 Casino Center Drive Maryland Heights MO
Fully refundableReserve now, pay when you stay
The price is $131 total per night from Nov 30 to Dec 1
$131 total
per night
Nov 30 - Dec 1
A casino, 7 restaurants, and a 24-hour gym are all featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, express check-out, ...
Opens in a new windowHollywood Casino & Hotel St. Louis
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
3550 Samuel Sheppard Drive St. Louis MO
Fully refundableReserve now, pay when you stay
The price is $122 total per night from Nov 22 to Nov 23
$122 total
per night
Nov 22 - Nov 23
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 6 conference rooms, along with free WiFi in public areas. ...
Opens in a new windowAngad Arts Hotel St. Louis, Tapestry Collection by Hilton
Pear Tree Inn St. Louis Near Union Station

Pear Tree Inn St. Louis Near Union Station

3 out of 5
2211 Market Street St. Louis MO
Fully refundableReserve now, pay when you stay
The price is $120 total per night from Nov 15 to Nov 16
$120 total
per night
Nov 15 - Nov 16
This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
Opens in a new windowPear Tree Inn St. Louis Near Union Station
Forest Park Hotel by MDR

Forest Park Hotel by MDR

3 out of 5
5915 Wilson Ave St. Louis MO
Fully refundableReserve now, pay when you stay
The price is $88 total per night from Nov 29 to Nov 30
$88 total
per night
Nov 29 - Nov 30
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling for business? Take advantage of the 24-hour business center, ...
Opens in a new windowForest Park Hotel by MDR
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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.

Frequently asked questions

What are the top kid-friendly hotels in Winchester?
From carefully considered amenities to extra space, kid-friendly hotels come with features that can help turn a nice family vacation into a fabulous one. These Winchester properties make getting away with children child's play: Charming Ballwin Home < 1 Mi to Vlasis Park! will help make your vacation the most memorable one yet. It features a variety of conveniences geared toward families, such as a barbecue grill and internet access. Alternatively, spend your nights enjoying the comforts of Spacious 4 bedroom home. Make the most of a playground, a nearby theme park and more here.
Where can I find cheap hotels in Winchester?
At Travelocity you'll find really nice hotels in Winchester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winchester rather than in Winchester. We may find you even better rates, too.
How do I find the best Winchester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Winchester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winchester?
The cheapest hotel in Winchester is $88. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winchester?
There are 1,976 hotels in Winchester on Travelocity.
What are the best hotels in Winchester?
Winchester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winchester for you!
When is the best time to visit Winchester?
If you want the joy of a fun-filled trip in peak season, visit Winchester during March, May and June. If you'd prefer the peace of off-season, book a stay during quieter months, such as January, October and December.
When is the cheapest time to stay in Winchester?
Based on historic data is usually the cheapest month to visit Winchester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winchester?
There are multiple hotels in Winchester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winchester. We have plenty of kid-friendly hotels in Winchester to choose from on Travelocity!
Why book a hotel in Winchester through Travelocity?
Because we have the top hotels in Winchester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winchester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Winchester hotel reviews by fellow wanderers

Pear Tree Inn St. Louis Airport

Pear Tree Inn St. Louis Airport

5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Staff is very accommodating."
A verified traveler stayed at Pear Tree Inn St. Louis Airport
Pear Tree Inn St. Louis Airport

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