Winchester Vacations from $226

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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.
Holiday Inn Express & Suites St. Louis West - Fenton by IHG

Holiday Inn Express & Suites St. Louis West - Fenton by IHG

3 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 19
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.8/10 Excellent! (1,001 reviews)
great hotel clean and staff was fantasic

Reviewed on Aug 3, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 27
found 23 hours ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
9.2/10 Wonderful! (1,558 reviews)
I loke staying at the wildwwod because I'm in st. Louis without being in st. Louis. The town around the hotel seems a little like a ghost town and there always seems to be a lot of road construction but the area needs a lot more road construction. The area has great dining options that aren't chains or fast food. The hotel is clean and staff is accommodating.

Reviewed on Aug 10, 2025

The Principal Hotel

The Principal Hotel

3.5 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 19
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.8/10 Exceptional! (111 reviews)
Love staying here! The staff is very nice & always making sure you have what you need!

Reviewed on Aug 10, 2025

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 19
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.2/10 Very Good! (760 reviews)
I booked online and paid via the app. When I arrived on site they explained they had overbooked and had no rooms available. The staff was amazing and went above and beyond and secured a room at another location. Thank you to the staff for taking care of us.

Reviewed on Jul 26, 2025

Home2 Suites by Hilton St. Louis Downtown

Home2 Suites by Hilton St. Louis Downtown

3 out of 5
Downtown West
Save 100% on your flight
per person
Oct 16 - Oct 19
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8/10 Very Good! (481 reviews)
The staff was very friendly and helpful! The breakfast was amazing.. this is where we will be staying everytime we come to st. Louis.

Reviewed on Aug 1, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Winchester

Busch Stadium

Busch Stadium

Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's great live music or attend a baseball game.

Busch Stadium
St. Louis Union Station

St. Louis Union Station

You can learn about the local history of St. Louis when you make a stop at a well-known site like St. Louis Union Station. Experience the area's fascinating museums or attend a baseball game.

St. Louis Union Station
Gateway Arch showing a city, a skyscraper and skyline

Gateway Arch

Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.

Gateway Arch

What to do in Winchester

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

$24
per adult
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
Best of St. Louis Small Group Tour w/ Arch & River Cruise

Best of St. Louis Small Group Tour w/ Arch & River Cruise

$169
per adult
84% of travellers recommend
Best of St. Louis Small Group Tour w/ Arch & River Cruise
St. Louis: Guided Small Group City Tour with River Cruise

St. Louis: Guided Small Group City Tour with River Cruise

$174
per adult
100% of travellers recommend
St. Louis: Guided Small Group City Tour with River Cruise
See all activities in Winchester

Winchester Hotel Deals

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
$119 nightly
The price is $140 total per night from Aug 22 to Aug 23
$140 total
Aug 22 - Aug 23
Total includes taxes and fees
8.4/10 Very Good! (3,948 reviews)
"Maybe im just use to staying at the Drury across the street. But too many " policies ". Make sure you allow plenty of time for them to get your car out of valet. Not kid friendly IMO. Clean hotel, spacious rooms. Very nice staff"

Reviewed on Aug 10, 2025

Hyatt 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
$123 nightly
The price is $143 total per night from Aug 13 to Aug 14
$143 total
Aug 13 - Aug 14
Total includes taxes and fees
8.2/10 Very Good! (2,044 reviews)
"Nice, clean, modern hotel. Good dinner options within hotel and fun coffee shop."

Reviewed on Aug 8, 2025

Hollywood Casino & Hotel St. Louis
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
$120 nightly
The price is $140 total per night from Sep 2 to Sep 3
$140 total
Sep 2 - Sep 3
Total includes taxes and fees
9.4/10 Exceptional! (2,921 reviews)
"Will be staying here from now on when attending anything in downtown St. Louis!"

Reviewed on Aug 10, 2025

Drury Plaza Hotel St. Louis at the Arch
See all 1,762 properties in Winchester
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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Frequently asked questions

How much does a Winchester vacation package cost?
You can snap up a vacation package to this top destination from $226 on Expedia. However, how much your vacation to Winchester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winchester?
You can usually find reduced prices and greater availability in January, October and December. Take a look at our cheap Winchester vacation packages and you could score some great off-season deals.
How many days is enough for Winchester?
Usually, a handful of days is enough to see the major attractions during your Winchester vacation. But if you prefer to have more time to unwind or go on day trips, think about extending your itinerary.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Winchester package deal straight away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winchester escape off to a flying start.
Is it cheaper to book a Winchester vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a personalized Winchester vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Winchester?
If you're planning a spur-of-the-moment Winchester vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
If you're anything like us, you love discovering new places but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Winchester vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.