Winchester Vacations from $274

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Save 100% on your flight
Price was $378, price is now $274 per person
$274
per person
Feb 14 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.2/10 Very Good! (779 reviews)
Staff was informative during check-in. Room was clean and the TV even had WELCOME with my name on it. Would stay here again.

Reviewed on Dec 22, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $590, price is now $298 per person
$298
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,600 reviews)
Breakfast great! Pool: hot tub being renovated.

Reviewed on Jan 12, 2026

White House at Grand Central

White House at Grand Central

4 out of 5
Grand Center
Save 100% on your flight
Price was $448, price is now $288 per person
$288
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.6/10 Excellent! (123 reviews)
Very clean and very friendly people

Reviewed on Nov 11, 2025

Hampton Inn By Hilton St Louis Airport

Hampton Inn By Hilton St Louis Airport

2.5 out of 5
Woodson Terrace
Save 100% on your flight
Price was $565, price is now $412 per person
$412
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (96 reviews)
I love the breakfast and the area itself. The staff were very helpful. They take care of their guess.

Reviewed on Jan 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
Save 100% on your flight
Price was $456, price is now $336 per person
$336
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,022 reviews)
I always love staying Angad art hotel!

Reviewed on Jan 11, 2026

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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
$70 nightly
The price is $80 total per night from Jan 15 to Jan 16
$80 total
Jan 15 - Jan 16
Total with taxes and fees
8.4/10 Very Good! (753 reviews)
Check-in was easy! No hassles! Room is clean and the TV works😊

Reviewed on Jan 7, 2026

Best Western Jacksonville Inn
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 out of 5
1725 W Morton Ave Jacksonville IL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $93 total per night from Jan 22 to Jan 23
$93 total
Jan 22 - Jan 23
Total with taxes and fees
8.8/10 Excellent! (501 reviews)
Our stay was great, the only negative feedback is regarding the comfort of the bed.

Reviewed on Jan 1, 2026

Hampton Inn Jacksonville
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

2.5 out of 5
2401 Holliday Ln Jacksonville IL
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $89 total per night from Feb 1 to Feb 2
$89 total
Feb 1 - Feb 2
Total with taxes and fees
9.2/10 Wonderful! (624 reviews)
I was pleasantly surprised at how nice and attentive the staff were here! I’d come back for that alone. The breakfast reminded me of the waffles I’ve had at the LaQuinta hotel chain which are delicious. Parking and area felt extremely safe which was a plus as well.

Reviewed on Jan 5, 2026

Sleep Inn & Suites South Jacksonville
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 $274 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.