
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
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
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
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
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
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
Winchester Hotel Deals

Best Western Jacksonville Inn
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

Sleep Inn & Suites South Jacksonville
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

Quality Inn Jacksonville near I-72
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
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















