Winchester Vacations from $374

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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.
HoteLumiere at the Arch - A Caesars Rewards Destination

HoteLumiere at the Arch - A Caesars Rewards Destination

4 out of 5
Downtown St. Louis
Save 100% on your flight
Price was $646, price is now $374 per person
$374
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
6.6/10 (1,001 reviews)
It was very nice resort

Reviewed on Nov 20, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,151, price is now $579 per person
$579
per person
Feb 15 - Feb 22
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to St. Louis (STL)
9.2/10 Wonderful! (1,600 reviews)
Everything was good except the hot tub was down.

Reviewed on Nov 25, 2025

Hampton Inn By Hilton St Louis Airport

Hampton Inn By Hilton St Louis Airport

2.5 out of 5
Woodson Terrace
Save 100% on your flight
Price was $819, price is now $500 per person
$500
per person
Feb 15 - Feb 22
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to St. Louis (STL)
8.8/10 Excellent! (96 reviews)
Staff was nice. Room was clean. Breakfast was hot!

Reviewed on Nov 23, 2025

DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
Save 100% on your flight
Price was $903, price is now $573 per person
$573
per person
Feb 15 - Feb 22
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to St. Louis (STL)
8.6/10 Excellent! (1,001 reviews)
Clean rooms, comfortable beds, kind and helpful staff such as Kim, Brandon at the front desk, Michelle our house keeper were all fantastic.

Reviewed on Nov 26, 2025

The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $653, price is now $418 per person
$418
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.6/10 Excellent! (1,002 reviews)
Great stay! The room could have been a tiny bit cleaner but nothing crazy! Mainly stains on the table and some dusty areas but beds and bathrooms were clean! The staff was super nice and the place was nicely decorated.

Reviewed on Nov 15, 2025

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Discover the most popular places to visit in Winchester

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 great live music 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
St. Louis Zoo

St. Louis Zoo

In the middle of St. Louis, meet the exotic and endangered animals that live in meticulously recreated ecosystems from all over the world.

St. Louis Zoo

What to do in Winchester

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

$32
per adult
St. Louis Ghost Tour: Sinister Sins & Shadows
Step into the shadows and discover the haunting tales of our city's past.

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

$30
per adult
100% of travellers recommend
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
See all activities in Winchester

Winchester Hotel Deals

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

4 out of 5
421 N 8th St St. Louis MO
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $120 total per night from Dec 8 to Dec 9
$120 total
Dec 8 - Dec 9
Total with taxes and fees
8.6/10 Excellent! (1,127 reviews)
Clean room and hotel was beautiful

Reviewed on Nov 26, 2025

Magnolia Hotel St. Louis, a Tribute Portfolio 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
$83 nightly
The price is $97 total per night from Nov 30 to Dec 1
$97 total
Nov 30 - Dec 1
Total with taxes and fees
7.4/10 Good! (1,242 reviews)
Great location

Reviewed on Nov 22, 2025

Forest Park Hotel by MDR
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
$95 nightly
The price is $111 total per night from Nov 30 to Dec 1
$111 total
Nov 30 - Dec 1
Total with taxes and fees
8.4/10 Very Good! (4,006 reviews)
Taylor, at the front desk, was amazing and so helpful. She answered my questions with ease during check-in, and continued to help throughout my stay. Taylor deserves a huge Thank you!

Reviewed on Nov 22, 2025

Hyatt Regency St. Louis at The Arch
See all 1,803 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.

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

How much does a Winchester vacation package cost?
You can snap up a vacation package to this top destination from $374 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.