Winchester Vacations from $526

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Pennywell St. Louis at the Arch

Hilton Pennywell St. Louis at the Arch

4 out of 5
Downtown St. Louis
Price was $686, price is now $526 per person
$526
per person
Jun 8 - Jun 12
found 7 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to St. Louis (STL)
8.8/10 Excellent! (1,029 reviews)
Nice and convenient to the event I was attending

Reviewed on Apr 4, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $882, price is now $606 per person
$606
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
9.2/10 Wonderful! (1,627 reviews)
The breakfaat was average, thou fresh. There was enough street parking nearby, safe.

Reviewed on Mar 30, 2026

The Cheshire

The Cheshire

4 out of 5
Price was $1,283, price is now $960 per person
$960
per person
May 12 - May 16
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) to St. Louis (STL)
8.6/10 Excellent! (1,009 reviews)
It had unique decor which was fun. Staff was nice But the lights were broken and there was a leftover can under a chair

Reviewed on Apr 1, 2026

Spacious 3-Bedroom with King Bed

Spacious 3-Bedroom with King Bed

4 out of 5
Central West End
Price was $1,316, price is now $1,040 per person
$1,040
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
8.8/10 Excellent! (11 reviews)
Clean room nice area

Reviewed on Feb 1, 2026

The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was $862, price is now $681 per person
$681
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
9.4/10 Exceptional! (505 reviews)
Great, simple breakfast options. Clean fitness room. Terrific location steps from main campus and a short walk to town and restaurants.

Reviewed on Mar 26, 2026

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Winchester Hotel Deals

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
$86 nightly
The price is $96 total per night from Apr 16 to Apr 17
$96 total
Apr 16 - Apr 17
Total with taxes and fees
9.4/10 Exceptional! (656 reviews)
Yes to both

Reviewed on Apr 3, 2026

Sleep Inn & Suites South Jacksonville
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
$75 nightly
The price is $85 total per night from Apr 6 to Apr 7
$85 total
Apr 6 - Apr 7
Total with taxes and fees
8.4/10 Very Good! (766 reviews)
Staff is great as usual .. been staying here for about 2 months now for work. Always clean and comfy

Reviewed on Apr 2, 2026

Best Western Jacksonville Inn
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

2.5 out of 5
200 Comfort Drive Jacksonville IL
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $75 total per night from May 4 to May 5
$75 total
May 4 - May 5
Total with taxes and fees
7.8/10 Good! (454 reviews)
Not the best not the worst

Reviewed on Apr 2, 2026

Quality Inn Jacksonville near I-72
See all 43 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
Population
1,500

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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $526 on Expedia for your Winchester getaway. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
You can usually find reduced prices and better availability in November, December and January. Take a look at our cheap Winchester vacation packages and you could land some great off-season deals.
How many days is enough for Winchester?
The ideal duration of your Winchester vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you enough time to tick off all the top attractions and explore some hidden treasures along the way.
How to find the best Winchester package deals?
Use Expedia's handy filters to find some terrific Winchester package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Winchester package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could land you great savings when compared to booking hotels and flights individually. Better still, you can personalize your Winchester trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Winchester?
Secure fantastic discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Winchester adventure.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Your Winchester break should be an escape from your busy life, not a source of money worries. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.