Winchester Vacation Packages

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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.

Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was CA $885, price is now CA $751 per person
CA $751
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
9.4/10 Exceptional! (376 reviews)
Quiet, unique. A little difficult to find the correct front entrance and parking.

Reviewed on Aug. 27, 2025

CentralWestEnd-WashU-STL- Euphoria

CentralWestEnd-WashU-STL- Euphoria

2 out of 5
Central West End
Price was CA $2,133, price is now CA $1,771 per person
CA $1,771
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
10/10 Exceptional! (1 review)
DoubleTree by Hilton St. Louis - Westport

DoubleTree by Hilton St. Louis - Westport

4 out of 5
Price was CA $987, price is now CA $837 per person
CA $837
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.2/10 Very Good! (1,002 reviews)
I liked how it was easy to park, easy to check in, the lighting wasn't too harsh, felt quiet and nice

Reviewed on Aug. 17, 2025

Country Inn & Suites by Radisson, St. Peters, MO

Country Inn & Suites by Radisson, St. Peters, MO

2.5 out of 5
Price was CA $850, price is now CA $754 per person
CA $754
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.2/10 Very Good! (1,003 reviews)
Everything was as advertised.

Reviewed on Aug. 27, 2025

DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
Price was CA $857, price is now CA $763 per person
CA $763
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Beautiful property, pleasant and responsive staff, delicious warm cookies! And convenient location near city hall and police department.

Reviewed on Jul. 27, 2025

Ready to book your vacation to Winchester?

 

Choose your dates

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
The price is CA $187 per night from Sep 1 to Sep 2
CA $187
CA $220 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (3,992 reviews)
"Lots of dinning walking distance, quiet, self parking can be sometimes full but they have valet for 10 dollars more."

Reviewed on Aug. 25, 2025

Hyatt Regency St. Louis at The Arch
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
The price is CA $176 per night from Sep 7 to Sep 8
CA $176
CA $206 total
Sep 7 - Sep 8
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
"Great"

Reviewed on Aug. 24, 2025

Renaissance St. Louis Airport Hotel
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
The price is CA $166 per night from Sep 28 to Sep 29
CA $166
CA $194 total
Sep 28 - Sep 29
includes taxes & fees
9.4/10 Exceptional! (2,984 reviews)
"The hotel was more than what we expected!! The breakfast was delicious and the kickback food and drinks were excellent! Not too mention that was all included! Will definitely return!!! Also huge shout out to all employees there.. everyone was so friendly and helpful!!"

Reviewed on Aug. 25, 2025

Drury Plaza Hotel St. Louis at the Arch
See all 1,772 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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Discover the most popular places to visit in Winchester

Busch Stadium

Busch Stadium

5/5(19 reviews)

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
Gateway Arch featuring modern architecture, a city and a skyscraper

Gateway Arch

4.5/5(37 reviews)

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

4.5/5(7 reviews)

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: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

CA $31
per adult
96% of travellers recommend
St Louis: City Museum General Admission Ticket
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

CA $44
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

CA $233
per adult
84% of travellers recommend
Best of St. Louis Small Group Tour w/ Arch & River Cruise
See all activities in Winchester

Frequently asked questions

How much does a Winchester vacation package cost?
You can snap up a vacation package to this top destination from CA $751 on Expedia. But how much your vacation to Winchester costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Winchester?
To score cheap Winchester vacation packages, organize your getaway outside of peak periods such as public holidays. You'll typically find better availability and lower prices for flights and hotels.
How many days is enough for Winchester?
With a well-organized itinerary, you can easily tick off the most popular Winchester attractions in a few days. But if you want to explore off the beaten track or take day trips, think about booking your Winchester vacation for longer.
How to find the best Winchester package deals?
Use Expedia's filters to find some tempting Winchester package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Winchester package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Winchester vacation as a package?
You can enjoy significant savings on your Winchester retreat by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Winchester?
If you've got your Winchester travel dates locked in, book early to score some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Winchester?

  1. Choose your travel dates: What you'd like to do in Winchester and your favourite season can help you decide when to go.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and experiences. Your accommodations will likely be the largest expense during your trip to Winchester.
  3. Decide how long to go away for: Now that you're up to speed on Winchester, you can figure out the ideal length of your break. Create a rough itinerary and give yourself enough time to get through everything on your must-do list.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a Winchester vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.