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Compare 1,772 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Our top choices for Winchester hotels

Pear Tree Inn St. Louis Arnold

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Location is excellent "
$90 nightly
The price is $104
Aug 27 - Aug 28
Total with taxes and fees
Pear Tree Inn St. Louis Arnold

Drury Inn & Suites St. Louis St. Peters

3.0 star property
9.2 out of 10, Wonderful, (1002)
"The stay was great. Friendly staff and breakfast options were excellent "
$110 nightly
The price is $126
Aug 31 - Sep 1
Total with taxes and fees
Drury Inn & Suites St. Louis St. Peters

Sleep Inn & Suites O'Fallon MO - Technology Drive

2.5 star property
8.8 out of 10, Excellent, (1002)
"Perfect place to stay, very clean and quiet."
$89 nightly
The price is $105
Aug 24 - Aug 25
Total with taxes and fees
Sleep Inn & Suites O'Fallon MO - Technology Drive

The Wildwood Hotel

3.5 star property
9.2 out of 10, Wonderful, (1555)
"Great place to stay."
$95 nightly
The price is $111
Sep 1 - Sep 2
Total with taxes and fees
The Wildwood Hotel

Pear Tree Inn St. Louis Airport

2.5 star property
9.4 out of 10, Exceptional, (2668)
"Great place to stay!"
$90 nightly
The price is $106
Aug 26 - Aug 27
Total with taxes and fees
Pear Tree Inn St. Louis Airport

River City Casino & Hotel

4.0 star property
9.0 out of 10, Wonderful, (1333)
"It was very nice there we would definitely stay again "
$114 nightly
The price is $133
Aug 24 - Aug 25
Total with taxes and fees
River City Casino & Hotel

Courtyard by Marriott St. Louis Chesterfield

3.0 star property
9.0 out of 10, Wonderful, (546)
"Great stay for our quick weekend get away. "
$112 nightly
The price is $130
Aug 29 - Aug 30
Total with taxes and fees
Courtyard by Marriott St. Louis Chesterfield

Drury Plaza Hotel St. Louis Chesterfield

3.0 star property
9.6 out of 10, Exceptional, (1001)
"Hotel was great "
$130 nightly
The price is $151
Aug 26 - Aug 27
Total with taxes and fees
Drury Plaza Hotel St. Louis Chesterfield

Drury Inn & Suites St. Louis Airport

3.0 star property
9.2 out of 10, Wonderful, (1036)
"The evening happy hour and morning breakfast are very nice and make the stay even better. The hotel staff are very nice and accommodating. Definitely would recommend this hotel."
$111 nightly
The price is $130
Aug 26 - Aug 27
Total with taxes and fees
Drury Inn & Suites St. Louis Airport

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

3.0 star property
8.4 out of 10, Very Good, (1001)
"Very good hotel for the price"
$89 nightly
The price is $103
Aug 31 - Sep 1
Total with taxes and fees
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

Best Western St. Louis Inn

2.5 star property
7.8 out of 10, Good, (1001)
"Great place to stay."
$74 nightly
The price is $85
Aug 27 - Aug 28
Total with taxes and fees
Best Western St. Louis Inn

Country Inn & Suites by Radisson, St. Charles Historic District

2.5 star property
9.4 out of 10, Exceptional, (1001)
"Great location, loved the staff, so nice and helpful. "
$105 nightly
The price is $121
Aug 24 - Aug 25
Total with taxes and fees
Country Inn & Suites by Radisson, St. Charles Historic District

Best Western St. Louis-Kirkwood Route 66

3.5 star property
8.4 out of 10, Very Good, (1259)
"Beds were comfortable, parking lot was easy to access, and several restaurants were within walking distance."
$99 nightly
The price is $115
Aug 24 - Aug 25
Total with taxes and fees
Best Western St. Louis-Kirkwood Route 66

Super 8 by Wyndham St Charles

2.0 star property
8.0 out of 10, Very Good, (1000)
"Great breakfast and awesome staff"
$78 nightly
The price is $90
Aug 28 - Aug 29
Total with taxes and fees
Super 8 by Wyndham St Charles

Hyatt Regency St. Louis at The Arch

4.0 star property
8.4 out of 10, Very Good, (3973)
"Great hotel"
$129 nightly
The price is $152
Aug 23 - Aug 24
Total with taxes and fees
Hyatt Regency St. Louis at The Arch

Drury Plaza Hotel St. Louis Creve Coeur

3.0 star property
9.2 out of 10, Wonderful, (1001)
"The staff and hotel were great. The provided hot breakfast and diner buffet was great!"
$115 nightly
The price is $133
Aug 31 - Sep 1
Total with taxes and fees
Drury Plaza Hotel St. Louis Creve Coeur

Drury Inn & Suites Southwest St. Louis

3.0 star property
9.4 out of 10, Exceptional, (1014)
"Awesome staff and super nice hotel!"
$115 nightly
The price is $135
Aug 31 - Sep 1
Total with taxes and fees
Drury Inn & Suites Southwest St. Louis

Holiday Inn Express St. Louis West - O'Fallon by IHG

2.5 star property
8.6 out of 10, Excellent, (765)
"Clean, great breakfast, and quiet!"
$105 nightly
The price is $124
Aug 24 - Aug 25
Total with taxes and fees
Holiday Inn Express St. Louis West - O'Fallon by IHG

Pear Tree Inn St. Louis Near Union Station

3.0 star property
8.8 out of 10, Excellent, (1572)
"Beautiful stay also bed is very comfortable good food as well "
$98 nightly
The price is $115
Aug 26 - Aug 27
Total with taxes and fees
Pear Tree Inn St. Louis Near Union Station

Best Western Plus The Charles Hotel

3.0 star property
8.0 out of 10, Very Good, (1000)
"best place i stayed at for a while 10/10 would recommend "
$88 nightly
The price is $102
Aug 26 - Aug 27
Total with taxes and fees
Best Western Plus The Charles Hotel
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.
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Learn more about Winchester

Venture to Museum of Transportation and The Factory—just two of the sights around Winchester.

Stay near popular Winchester attractions

Top Winchester Hotel Reviews

Frequently asked questions

Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Winchester hotel for you.
How can I save on a Winchester hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Winchester hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

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How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from $71 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.