Winchester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to St. Louis (STL)
8.2/10 Very Good! (754 reviews)
The stay was too short

Reviewed on Jul. 2, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to St. Louis (STL)
9/10 Wonderful! (1,547 reviews)
Fantastic accommodations staff that went out of their way to make sure I was comfortable and taken care of I recommend this hotel to anyone

Reviewed on Jul. 10, 2025

Ballpark Apartments by Barsala

Ballpark Apartments by Barsala

4 out of 5
Downtown St. Louis
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to St. Louis (STL)
7.2/10 Good! (7 reviews)
It's a great location, right across from the Ballpark. It is a fairly spartan apartment set-up, with concrete floors.. a little surprising? Parking is on the street or in a pay lot.

Reviewed on Jun. 8, 2025

HoteLumiere at the Arch

HoteLumiere at the Arch

4 out of 5
Downtown St. Louis
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to St. Louis (STL)
6.6/10 (1,000 reviews)
I like that it was right across from the casino. I didnt like that it was card only no cash and didnt offer no breakfast only one vending machine and it offered baked food but only 3 options.

Reviewed on Jun. 30, 2025

Hilton Garden Inn St. Louis/O'Fallon MO

Hilton Garden Inn St. Louis/O'Fallon MO

3 out of 5
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to St. Louis (STL)
8.8/10 Excellent! (686 reviews)
The food in the restaurant was terrable. I had the meat balls and I could not eat them

Reviewed on Jun. 30, 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 $189 per night from Jul 31 to Aug 1
CA $189
CA $223 total
Jul 31 - Aug 1
includes taxes & fees
8.4/10 Very Good! (3,822 reviews)
"I like where it was located. The sink and toilet didn't drain well."

Reviewed on Jul. 9, 2025

Hyatt Regency St. Louis at The Arch
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 $192 per night from Jul 17 to Jul 18
CA $192
CA $224 total
Jul 17 - Jul 18
includes taxes & fees
9.4/10 Exceptional! (2,846 reviews)
A+ Hotel Stay
"From the moment we checked in until leaving, the service was top notch. At the dinner, it was super crowded, but employees were coming through quickly to clean tables and get them ready for the next person. Breakfast was yummy. Love the location!"

Reviewed on Jul. 11, 2025

Drury Plaza Hotel St. Louis at the Arch
The Arch Convention Hotel
The Arch Convention Hotel
3.5 out of 5
811 N 9th Street, St. Louis, MO
Fully refundable
The price is CA $155 per night from Jul 14 to Jul 15
CA $155
CA $181 total
Jul 14 - Jul 15
includes taxes & fees
6.8/10 (1,007 reviews)
"The water was not working and turned off mid shower, was told be on in 10-15 minutes, still not on 45 minutes later"

Reviewed on Jul. 9, 2025

The Arch Convention Hotel
See all 1,800 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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
94% of travellers recommend
St Louis: City Museum General Admission Ticket
St. Louis Arch Walking Tour and Entrance Ticket

St. Louis Arch Walking Tour and Entrance Ticket

CA $69
per adult
St. Louis Arch Walking Tour and Entrance Ticket
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

CA $33
per adult
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
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 $678 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.