Winchester Vacations from $408

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

4 out of 5
Downtown St. Louis
Price was $605, price is now $408 per person
$408
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to St. Louis (STL)
8.8/10 Excellent! (1,096 reviews)
The staff was amazing but the facility itself was not very clean. There was dust, dirty vents in the room, and carpet stains in the hallway.

Reviewed on Nov 26, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $833, price is now $456 per person
$456
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to St. Louis (STL)
9.2/10 Wonderful! (1,600 reviews)
The hot tub didnt work. It didnt have the table arrangement as advertised in the picture. The suite was very small.

Reviewed on Nov 28, 2025

HoteLumiere at the Arch - A Caesars Rewards Destination

HoteLumiere at the Arch - A Caesars Rewards Destination

4 out of 5
Downtown St. Louis
Save 100% on your flight
Price was $762, price is now $465 per person
$465
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to St. Louis (STL)
6.6/10 (1,001 reviews)
It was very nice resort

Reviewed on Nov 20, 2025

Hampton Inn By Hilton St Louis Airport

Hampton Inn By Hilton St Louis Airport

2.5 out of 5
Woodson Terrace
Price was $635, price is now $424 per person
$424
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to St. Louis (STL)
8.8/10 Excellent! (96 reviews)
Staff was nice. Room was clean. Breakfast was hot!

Reviewed on Nov 23, 2025

The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $726, price is now $498 per person
$498
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to St. Louis (STL)
8.6/10 Excellent! (1,002 reviews)
Great stay! The room could have been a tiny bit cleaner but nothing crazy! Mainly stains on the table and some dusty areas but beds and bathrooms were clean! The staff was super nice and the place was nicely decorated.

Reviewed on Nov 15, 2025

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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 Nov 30 to Dec 1
$85 total
Nov 30 - Dec 1
Total with taxes and fees
8.4/10 Very Good! (738 reviews)
Clean, quiet, easy, secure access, friendly front desk staff. Breakfast room clean and organized, staff friendly and helpful.

Reviewed on Nov 21, 2025

Best Western Jacksonville Inn
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

2.5 out of 5
2401 Holliday Ln Jacksonville IL
Fully refundable
$78 nightly
The price is $87 total per night from Dec 18 to Dec 19
$87 total
Dec 18 - Dec 19
Total with taxes and fees
9.2/10 Wonderful! (615 reviews)
Friendly and inviting staff. Clean bathrooms and overall nice hotel.

Reviewed on Nov 25, 2025

Sleep Inn & Suites South Jacksonville
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
$63 nightly
The price is $70 total per night from Dec 6 to Dec 7
$70 total
Dec 6 - Dec 7
Total with taxes and fees
7.6/10 Good! (423 reviews)
Staff was very nice. Room was great. A few things in the room were outdated (fabric on chair needed mending) but that didn’t keep us from having a pleasant stay. Plenty of parking.

Reviewed on Nov 16, 2025

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 $408 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.