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 Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was CA $1,395, price is now CA $1,060 per person
CA $1,060
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Louis (STL)
9.2/10 Wonderful! (1,650 reviews)

The Cheshire

The Cheshire

4 out of 5
Price was CA $1,560, price is now CA $1,271 per person
CA $1,271
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
8.8/10 Excellent! (1,010 reviews)
The Cheshire is our home away from home in St Louis. We’ve stayed here at least seven times in the last thirteen years and have never been disappointed. The location is so central with great highway access that it’s hard to be more than twenty minutes from most places to visit.

Reviewed on Jul 25, 2026

Crowne Plaza St. Louis Airport by IHG

Crowne Plaza St. Louis Airport by IHG

3.5 out of 5
Price was CA $1,719, price is now CA $1,471 per person
CA $1,471
per person
Aug 24 - Aug 31
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8/10 Very good! (1,004 reviews)

Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
Price was CA $1,398, price is now CA $1,220 per person
CA $1,220
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Louis (STL)
9/10 Wonderful! (2,015 reviews)
Always amazing! This was our seventh trip and we’ll continue to say!

Reviewed on Jul 25, 2026

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was CA $1,481, price is now CA $1,299 per person
CA $1,299
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
8.6/10 Excellent! (1,019 reviews)

Ready to book your vacation to Winchester?

 

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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 $214 per night from Jul 31 to Aug 1
CA $214
CA $253 total
Jul 31 - Aug 1
includes taxes & fees
Hyatt Regency St. Louis at The Arch
Clayton Plaza Hotel & Extended Stay

Clayton Plaza Hotel & Extended Stay

3.5 out of 5
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Aug 16 to Aug 17
CA $139
CA $162 total
Aug 16 - Aug 17
includes taxes & fees
9/10 Wonderful! (3,273 reviews)
"Although the hotel was nice, I didn’t realize it was downtown much less that parking was in a parking garage. It was completely on the other side, which you had to go around a couple blocks to get to it. Even thought it was attached, the elevator to the garage was out of order. So it was impossible ..."

Reviewed on Jul 25, 2026

Clayton Plaza Hotel & Extended Stay
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
The price is CA $183 per night from Aug 2 to Aug 3
CA $183
CA $234 total
Aug 2 - Aug 3
includes taxes & fees
8.6/10 Excellent! (2,207 reviews)
"Hotel is convenient when attending a concert. Ate at the pub, and food was decent & service was friendly. Our room was clean, but bed was a bit squeaky and pillows could be better. But worked for what we needed. Hotel common spaces (eg. lobby) smells pretty well of cigarettes even though we didn’t ..."

Reviewed on Jul 24, 2026

Hollywood Casino & Hotel St. Louis
See all 1,993 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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What to do in Winchester

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

CA $34
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
The Gateway Arch National Park & Museum

StL's Signature "Sights and Bites" - Private Tour in St. Louis

CA $234
per adult
StL's Signature "Sights and Bites" - Private Tour in St. Louis
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

CA $36
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking 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 $1,060 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.