Winchester Vacations from $261

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton St. Louis Forest Park

DoubleTree by Hilton St. Louis Forest Park

4 out of 5
Central West End
Price was $346, price is now $261 per person
$261
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.2/10 Very Good! (1,006 reviews)
Friendly staff, very responsive. Room was comfortable and very convenient if you’re accessing the medical facilities for Washington University and Barnes Jewish Hospital.

Reviewed on Oct 14, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $871, price is now $575 per person
$575
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,581 reviews)
Has a parking garage or street parking patrolled by local police constantly. We did not try the hotel breakfast we went to “The Pancake House” for breakfast and it was awesome.

Reviewed on Oct 12, 2025

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 $432, price is now $305 per person
$305
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,005 reviews)
Awesome hotel with awesome/helpful staff! The area around is mostly safe, nighttime can get a lil scary but the hotel itself is really safe.

Reviewed on Oct 11, 2025

Hampton Inn By Hilton St Louis Airport

Hampton Inn By Hilton St Louis Airport

2.5 out of 5
Woodson Terrace
Price was $406, price is now $287 per person
$287
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (62 reviews)
One night stay to catch a flight Easy check in, room was clean and ready for us Shuttle to airport was right on schedule Excellent experience

Reviewed on Oct 13, 2025

DoubleTree by Hilton St. Louis - Westport

DoubleTree by Hilton St. Louis - Westport

4 out of 5
Price was $397, price is now $300 per person
$300
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.2/10 Very Good! (1,004 reviews)
The property was very nice however, my main kudos goes to the staff. There was a plumbing issue. They got me to another room and will refund a one night‘s stay

Reviewed on Sep 29, 2025

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Winchester Hotel Deals

Sleep Inn & Suites

Sleep Inn & Suites

2.5 out of 5
2401 Holliday Ln, Jacksonville, IL
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $93 total per night from Nov 6 to Nov 7
$93 total
Nov 6 - Nov 7
Total with taxes and fees
9.2/10 Wonderful! (594 reviews)
"Great stay!"

Reviewed on Oct 9, 2025

Sleep Inn & Suites
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 Oct 16 to Oct 17
$85 total
Oct 16 - Oct 17
Total with taxes and fees
8.4/10 Very Good! (721 reviews)
Terrific
"Terrific."

Reviewed on Oct 12, 2025

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
$59 nightly
The price is $66 total per night from Nov 14 to Nov 15
$66 total
Nov 14 - Nov 15
Total with taxes and fees
7.6/10 Good! (407 reviews)
"The air conditioning didn't work the first night until we fidgeted with it for some time. The breakfast the first day was good but the 2nd day the food wasn't available due to excess demand that wasn't being met."

Reviewed on Oct 6, 2025

Quality Inn Jacksonville near I-72
See all 42 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.

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 $261 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.