Book Hotels in Winchester, MO

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Top Winchester hotels

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
$134 nightly
The price is $157 total per night from Feb 26 to Feb 27
$157 total
Feb 26 - Feb 27
Total with taxes and fees
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. ...
The room was spotless and staff were outstanding. This is our first stay at a Drury Hotel and we will now seek them out when traveling.

Reviewed on Feb 16, 2026

Opens in a new windowDrury Plaza Hotel St. Louis at the Arch
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
$89 nightly
The price is $105 total per night from Feb 26 to Feb 27
$105 total
Feb 26 - Feb 27
Total with taxes and fees
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 ...
We have always received good service at this hotel. The bed is comfortable and the bedroom has a nice layout. The price beats all of the surrounding competition. But, the best part of this hotel is the outstanding breakfast!

Reviewed on Feb 17, 2026

Opens in a new windowPear Tree Inn St. Louis Airport
Live by Loews - St.Louis

Live by Loews - St.Louis

4 out of 5
799 Clark ave St. Louis MO
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $177 total per night from Feb 22 to Feb 23
$177 total
Feb 22 - Feb 23
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet ...
Everything was 10 star

Reviewed on Feb 14, 2026

Opens in a new windowLive by Loews - St.Louis
21C Museum Hotel St Louis

21C Museum Hotel St Louis

4.5 out of 5
1528 Locust street St. Louis MO
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $153 total per night from Mar 15 to Mar 16
$153 total
Mar 15 - Mar 16
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...
Pleasant staff

Reviewed on Feb 17, 2026

Opens in a new window21C Museum Hotel St Louis
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
$105 nightly
The price is $123 total per night from Feb 26 to Feb 27
$123 total
Feb 26 - Feb 27
Total with taxes and fees
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 ...
Love this older hotel that has kept up with the times. Love the excellent hot buffet breakfast, including cooked to order omelettes, that comes with the price of the room. Disappointed that the garage parking is no longer free, but hey, I can handle six dollars a night. Can’t beat the price for the ...

Reviewed on Feb 16, 2026

Opens in a new windowClayton Plaza Hotel & Extended Stay
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
$92 nightly
The price is $108 total per night from Mar 5 to Mar 6
$108 total
Mar 5 - Mar 6
Total with taxes and fees
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. ...
great location and parking

Reviewed on Feb 16, 2026

Opens in a new windowPear Tree Inn St. Louis Near Union Station
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
$106 nightly
The price is $126 total per night from Feb 22 to Feb 23
$126 total
Feb 22 - Feb 23
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and ...
Zero complaints! Enjoyed our stay and will stay again!

Reviewed on Feb 15, 2026

Opens in a new windowMagnolia Hotel St. Louis, a Tribute Portfolio Hotel
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
$149 nightly
The price is $176 total per night from Feb 27 to Feb 28
$176 total
Feb 27 - Feb 28
Total with taxes and fees
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 ...
Perfect!

Reviewed on Feb 18, 2026

Opens in a new windowHyatt Regency St. Louis at The Arch
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

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

3 out of 5
1088 South Highway Drive Fenton MO
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $103 total per night from Feb 22 to Feb 23
$103 total
Feb 22 - Feb 23
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the ...
Everything was good

Reviewed on Feb 16, 2026

Opens in a new windowHeritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham
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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 $103. 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 1,864 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

Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Perfect!"
A verified traveler stayed at Hyatt Regency St. Louis at The Arch
Hyatt Regency St. Louis at The Arch

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