Book Hotels in Winchester, MO

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Top Winchester hotels

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
$90 nightly
The price is $106 total per night from Apr 13 to Apr 14
$106 total
Apr 13 - Apr 14
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 ...
Great stay I have no complains

Reviewed on Apr 6, 2026

Opens in a new windowPear Tree Inn St. Louis Airport
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
$137 nightly
The price is $163 total per night from May 4 to May 5
$163 total
May 4 - May 5
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. ...
Welcoming, very kind staff

Reviewed on Apr 5, 2026

Opens in a new windowDrury Inn & Suites St. Louis Union Station
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
$148 nightly
The price is $173 total per night from May 3 to May 4
$173 total
May 3 - May 4
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, ...
We had a double queen room and one bed didn’t have a comforter. We checked in with 4 adults but only had 3 towels in the bathroom. On the second day we asked for a comforter for the second bed and extra towels and then never received them. Elevators are a pain in the behind also. We did love all ...

Reviewed on Apr 6, 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
$94 nightly
The price is $110 total per night from Apr 19 to Apr 20
$110 total
Apr 19 - Apr 20
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 ...
The room was very clean, there was always someone at the front desk and each staff member I encountered was friendly. The breakfast buffet was a nice bonus. Overall 10/10.

Reviewed on Apr 6, 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
$113 nightly
The price is $132 total per night from Apr 13 to Apr 14
$132 total
Apr 13 - Apr 14
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. ...
My kids appreciated the pool (crowded as it was!). The happy hour and fountain soda in the breakfast area was a pleasant surprise. Rooms are a bit worn, hallway looked like it had some water issues as well with missing tiles/exposed pipes. Bed was too soft for me. We had to switch rooms due to wet ...

Reviewed on Apr 6, 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
$136 nightly
The price is $160 total per night from May 8 to May 9
$160 total
May 8 - May 9
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 ...
Nice stay at an older downtown hotel. Was in walking distance of most attractions we were in town for. Very quiet even though there were several middle and high school girls volleyball teams in town for a tournament. Would definitely stay there again.

Reviewed on Apr 6, 2026

Opens in a new windowHyatt Regency St. Louis at The Arch
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
$122 nightly
The price is $143 total per night from Apr 8 to Apr 9
$143 total
Apr 8 - Apr 9
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, ...
It is an ok place

Reviewed on Apr 6, 2026

Opens in a new windowHollywood Casino & Hotel St. Louis
Best Western St. Louis-Kirkwood Route 66

Best Western St. Louis-Kirkwood Route 66

3.5 out of 5
1200 S Kirkwood Road Kirkwood MO
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $110 total per night from Apr 12 to Apr 13
$110 total
Apr 12 - Apr 13
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free ...
If I could give this place zero stars I would. They sold us a room with no working A/C, knowing it doesn’t work. Said they were sold out of other rooms and we couldn’t change when we realized. Didn’t give us any compensation to make up for it except a box fan. Will never stay here or any Best Western ...

Reviewed on Apr 2, 2026

Opens in a new windowBest Western St. Louis-Kirkwood Route 66
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
$162 nightly
The price is $189 total per night from Apr 12 to Apr 13
$189 total
Apr 12 - Apr 13
Total with taxes and fees
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
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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 $106. 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 1,904 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

Hilton St. Louis Airport

Hilton St. Louis Airport

5 out of 5
Posted 8 hours ago
Travelocity Verified Review
"Love this hotel! Very convenient and modern!"
A verified traveler stayed at Hilton St. Louis Airport
Hilton St. Louis Airport

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