Book Hotels in Winchester, MO

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Property amenities
Property amenities
Accessibility
Accessibility

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
$153 nightly
The price is $179 total per night from Aug 9 to Aug 10
$179 total
Aug 9 - Aug 10
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 ...
"None"

Reviewed on Aug 5, 2026

Opens in a new windowDrury Plaza Hotel St. Louis at the Arch
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
$159 nightly
The price is $189 total per night from Aug 9 to Aug 10
$189 total
Aug 9 - Aug 10
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 ...
"Great location."

Reviewed on Aug 5, 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
$91 nightly
The price is $106 total per night from Aug 30 to Aug 31
$106 total
Aug 30 - Aug 31
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 ...
"From walking in the grand entrance to the incredible high tech showers, it was a great experience. The hot breakfast bar really was impressive and hit the spot before having to drive all day to our next destination. My only complaint was that the game room is temporarily out of order due to remodeling, ..."

Reviewed on Aug 5, 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
$122 nightly
The price is $143 total per night from Aug 9 to Aug 10
$143 total
Aug 9 - Aug 10
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. ...
"This as hands down the best place I have stayed at so far very friendly people and helpful"

Reviewed on Aug 5, 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
$134 nightly
The price is $158 total per night from Aug 28 to Aug 29
$158 total
Aug 28 - Aug 29
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 ...
"Getting little dated! Elevators really slow!!"

Reviewed on Aug 5, 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
$134 nightly
The price is $157 total per night from Aug 10 to Aug 11
$157 total
Aug 10 - Aug 11
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, ...
"No problems, quick service and clean facilities. Would stay again if in the area."

Reviewed on Aug 5, 2026

Opens in a new windowHollywood Casino & Hotel St. Louis
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
$111 nightly
The price is $130 total per night from Aug 28 to Aug 29
$130 total
Aug 28 - Aug 29
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 ...
"Timely"

Reviewed on Aug 4, 2026

Opens in a new windowRenaissance St. Louis Airport Hotel
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
$97 nightly
The price is $113 total per night from Aug 10 to Aug 11
$113 total
Aug 10 - Aug 11
Total with taxes and fees
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, ...
"Had to wait on front desk several minutes. Had to ask for wifi password. Microwave didn't heat food that well."

Reviewed on Aug 5, 2026

Opens in a new windowForest Park Hotel by MDR
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
$94 nightly
The price is $109 total per night from Aug 9 to Aug 10
$109 total
Aug 9 - Aug 10
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 ...
Opens in a new windowHeritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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 2,005 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

4 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Getting little dated! Elevators really slow!!"
A verified traveler stayed at Hyatt Regency St. Louis at The Arch
Hyatt Regency St. Louis at The Arch

Explore More Ways to Travel with Travelocity