Winchester Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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 $1,122, price is now CA $888 per person
CA $888
per person
Aug 22 - Aug 24
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
9.2/10 Wonderful! (1,661 reviews)
Absolutely beautiful property, such a unique looking hotel. The parking garage was a big help keeping my car safe during storms!

Reviewed on Jul 14, 2026

Landing Furnished Apartments - Central West End

Landing Furnished Apartments - Central West End

3.5 out of 5
Central West End
Price was CA $1,660, price is now CA $1,479 per person
CA $1,479
per person
Oct 9 - Oct 12
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
7/10 Good! (4 reviews)
Parking was behind a large mechanical gate which did not always work. Could sometimes be noisy outside in the evening due to college clientele. Had to park on the street most of the time because of gate issues.

Reviewed on Jul 6, 2026

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was CA $1,122, price is now CA $1,023 per person
CA $1,023
per person
Aug 22 - Aug 24
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Our King room was really luxurious! Perfect for spending a night for my birthday. Staff was great everywhere we went from security at entrance to casino to wait staff at all 3 restaurants we tried. Pool was great too. We will b back!

Reviewed on Jul 13, 2026

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Price was CA $1,338, price is now CA $1,224 per person
CA $1,224
per person
Oct 9 - Oct 12
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8.8/10 Excellent! (1,061 reviews)
Excellent staff and the most comfortable beds! We had the green room with the tub and it was immaculate. This is the second time we have stayed at the Angad and both experiences have been great. They also have a rooftop bar with views of the entire city although it was woefully understaffed. The bartender did the best she could but seemed a little overwhelmed. No worries from us...we were there to relax and have a nightcap. Highly recommend giving it a try!

Reviewed on Jul 14, 2026

DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
Price was CA $1,015, price is now CA $945 per person
CA $945
per person
Aug 22 - Aug 24
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,002 reviews)
Very friendly

Reviewed on Jul 14, 2026

Ready to book your vacation to Winchester?

 

Choose your dates

Winchester Hotel Deals

Best Western Jacksonville Inn

Best Western Jacksonville Inn

2.5 out of 5
1709 W Morton Ave Jacksonville IL
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Jul 19 to Jul 20
CA $105
CA $120 total
Jul 19 - Jul 20
includes taxes & fees
8.4/10 Very good! (817 reviews)
"Great, helpful staff. Was clean but had large stain on carpet in our room."

Reviewed on Jul 8, 2026

Best Western Jacksonville Inn
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

3 out of 5
2401 Holliday Ln Jacksonville IL
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Jul 26 to Jul 27
CA $127
CA $141 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (710 reviews)
"Very nice welcoming front desk staff. Pool and pool table, plus some casino style gaming (I think. We didn't do this). Typical chain hotel but nothing broken or worn out! Hot breakfast."

Reviewed on Jul 6, 2026

Sleep Inn & Suites South Jacksonville
Jacksonville Inn & Suites

Jacksonville Inn & Suites

2 out of 5
1914 Southbrooke Rd Jacksonville IL
Fully refundableReserve now, pay when you stay
The price is CA $80 per night from Jul 18 to Jul 19
CA $80
CA $89 total
Jul 18 - Jul 19
includes taxes & fees
7.6/10 Good! (32 reviews)
"Newly renovated rooms are nice. Nothing special but still nice."

Reviewed on Jul 7, 2026

Jacksonville Inn & Suites
See all 73 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'll find cheap prices from CA $888 on Expedia for your Winchester getaway. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
January, February and November are great times to look for cheap Winchester vacation packages. Travelling in less busy months means you can typically find lower prices on accommodations and flights.
How many days is enough for Winchester?
With a well-organized itinerary, you can easily visit the main Winchester attractions in a few days. But if you want to discover lesser-known spots or go on day trips, consider booking your Winchester vacation for longer.
How to find the best Winchester package deals?
Bagging a cheap Winchester package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, add a few filters and see what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most economical Winchester package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester vacation as a package?
You can enjoy significant savings on your Winchester escape by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winchester?
If you're considering a spontaneous Winchester adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Winchester?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Winchester.
  2. Calculate your budget: Make sure you have enough money to cover everything from meals and transportation to activities and flights. Your accommodations will probably be the biggest expense during your trip to Winchester.
  3. Decide how long to go for: Now that you're more familiar with Winchester, you can figure out the ideal length of your break. Create a draft plan and allocate enough time to get through everything on your must-do list.
  4. Combine your airfare and accommodations: Once you've nailed down your travel dates and duration, lock in the ideal Winchester vacation package for you.

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