Winchester Vacations from $244
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Your Winchester Vacation
When a fun city break is calling, answer it with a Winchester vacation package. The neighborhood of Maplewood, which is great for bars and pubs, gift and craft shops and dining, makes a terrific base for your adventures. There's plenty to include on your itinerary during your trip to Winchester, starting with top attractions such as Castlewood State Park and American Kennel Club Museum of the Dog. Your Winchester vacation is just clicks away. Explore hotels, flights and more on Expedia for a getaway that's tailored just for you.
The Latest Winchester vacation packages
Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott St Louis Downtown
Midtown
Price was $910, price is now $595 per person
$595
per person
Sep 21 - Sep 25
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
7.8/10 Good! (1,001 reviews)
Poor quality and not clean. No up keep on the Property. Dirty pull out couch, so much that I wouldn’t put my kid on it. Bathroom door would not close.
Reviewed on Jul 1, 2026
Moonrise Hotel
Delmar Loop
Save 100% on your flight
Price was $414, price is now $287 per person
$287
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9/10 Wonderful! (1,976 reviews)
Beware if your room is on the 7th floor. The rooftop bar directly above is loud. as. hell. for. HOURS.
Reviewed on Jul 1, 2026
The Cheshire
Save 100% on your flight
Price was $458, price is now $324 per person
$324
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,004 reviews)
The Cheshire is a unique and beautiful place in a great location. That being said, it has some need of attention. While the room was comfortable, AC was quite loud and the overall cleanliness was not up to the expected standards. Example of cleanliness closet was dusty mentioned air conditioner Had lint buildup table. Obviously hadn’t legs had not been dusted. Overall, it was a wonderful visit and I would return. You just always hope these sort of places get the love and attention. They deserve.
Reviewed on Jul 2, 2026
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton
Grand Center
Save 100% on your flight
Price was $413, price is now $309 per person
$309
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,058 reviews)
Style of the premises, decor, and cleanliness were outstanding.
Reviewed on Jul 2, 2026
What to do in Winchester
St. Louis Ghost Tour: Sinister Sins & Shadows
$24
per adult
100% of travellers recommend
St. Louis Premium Small Group Tour With Arch & River Cruise
$161
per adult
84% of travellers recommend
St. Louis Premium Driving Tour with Boat Ride & Arch
$174
per adult
100% of travellers recommend
Winchester Hotel Deals
Hyatt Regency St. Louis at The Arch
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $165 total per night from Jul 17 to Jul 18
$165 total
Jul 17 - Jul 18
Total with taxes and fees
8.6/10 Excellent! (4,169 reviews)
"Our room faced towards the Gateway Arch/church. Very clean hotel. Staff was awesome. The restaurants were bith really good"
Reviewed on Jul 2, 2026
Clayton Plaza Hotel & Extended Stay
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $112 total per night from Jul 12 to Jul 13
$112 total
Jul 12 - Jul 13
Total with taxes and fees
8.8/10 Excellent! (3,252 reviews)
"The main parking garage was down so we had to park somewhere else which wasn’t convenient at all. They want to hold $100 for any damages that may occur while you’re staying there. The first night out we had to get a different room due to the refrigerator not working and the pull out couch was broke ..."
Reviewed on Jul 1, 2026
Pear Tree Inn St. Louis Airport
10810 Pear Tree Ln St. Ann MO
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $104 total per night from Jul 15 to Jul 16
$104 total
Jul 15 - Jul 16
Total with taxes and fees
9.2/10 Wonderful! (3,052 reviews)
"Nice place to stay"
Reviewed on Jul 2, 2026
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.
Find the Best Winchester Vacation Packages
Winchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Lambert-St. Louis Intl. Airport (STL) |
Population | 1,550 |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
