Book Hotels in Winchester, MO

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May 22 - May 24
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Top Winchester hotels

Drury Inn & Suites St. Louis Union Station

Drury Inn & Suites St. Louis Union Station

3 out of 5
201 S 20th St St. Louis MO
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $175 total per night from May 31 to Jun 1
$175 total
May 31 - Jun 1
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. ...
"We brought the grandkids there.. we had an excellent experience, right next door to the Union Station. Everything at the Union Station is very expensive that was the only downfall.."

Reviewed on May 22, 2026

Opens in a new windowDrury Inn & Suites St. Louis Union Station
Live by Loews - St.Louis

Live by Loews - St.Louis

4 out of 5
799 Clark ave St. Louis MO
$159 nightly
The price is $189 total per night from May 24 to May 25
$189 total
May 24 - May 25
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 ...
"Absolutely loved our stay here! The hotel was clean, comfortable, and had such a welcoming atmosphere. But the highlight of the experience was definitely the girl at check-in — she was so friendly, helpful, and genuinely kind from the moment we walked in. After a long day of traveling, her positive ..."

Reviewed on May 22, 2026

Opens in a new windowLive by Loews - 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
$98 nightly
The price is $114 total per night from Jun 7 to Jun 8
$114 total
Jun 7 - Jun 8
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 ...
"Everything was great!"

Reviewed on May 22, 2026

Opens in a new windowClayton Plaza Hotel & Extended Stay
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
$143 nightly
The price is $168 total per night from May 25 to May 26
$168 total
May 25 - May 26
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, ...
"The rooms were clean and common areas well maintained. Breakfast was the best and the staff were all helpful and very kind to all guests. It was the best stay I've had in a hotel."

Reviewed on May 21, 2026

Opens in a new window21C Museum Hotel St Louis
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
$116 nightly
The price is $136 total per night from May 31 to Jun 1
$136 total
May 31 - Jun 1
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. ...
"Nice hotel. Close to many things."

Reviewed on May 22, 2026

Opens in a new windowPear Tree Inn St. Louis Near Union Station
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
$127 nightly
The price is $149 total per night from May 25 to May 26
$149 total
May 25 - May 26
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 ...
"Short walk to Busch Stadium. Definitely recommend."

Reviewed on May 22, 2026

Opens in a new windowHyatt Regency St. Louis at The Arch
Renaissance St. Louis Airport Hotel

Renaissance St. Louis Airport Hotel

4 out of 5
9801 Natural Bridge Road St. Louis MO
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $148 total per night from May 29 to May 30
$148 total
May 29 - May 30
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, laundry service, and ...
"Xxx Essex d z"

Reviewed on May 22, 2026

Opens in a new windowRenaissance St. Louis Airport Hotel
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
$99 nightly
The price is $115 total per night from May 24 to May 25
$115 total
May 24 - May 25
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 ...
"Paid for an upgraded suite only to be told at check in - the room had never been cleaned and we were downgraded to a small room with only 2 beds for 3 adults. At first, we were offered a room with one king bed, so at least grateful for the second option. We were still charged the upgraded price and ..."

Reviewed on May 21, 2026

Opens in a new windowHeritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham
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
$116 nightly
The price is $136 total per night from Jun 1 to Jun 2
$136 total
Jun 1 - Jun 2
Total with taxes and fees
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
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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 $114. 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 1,899 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 Near Union Station

Pear Tree Inn St. Louis Near Union Station

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Nice hotel. Close to many things."
A verified traveler stayed at Pear Tree Inn St. Louis Near Union Station
Pear Tree Inn St. Louis Near Union Station

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