Winchester Vacations from $332

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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
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.2/10 Very Good! (754 reviews)
The stay was too short

Reviewed on Jul 2, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9/10 Wonderful! (1,547 reviews)
The room was ok, tired decor (a mix between The Sopranos and Hobby Lobby), slightly dirty furniture (sofa and arm chair). Bathroom was clean, fan didn’t pull all the moisture out. We traveled for a medical appointment in Saint Louis and I barely got any rest on the cheap springy mattress (we are 40, and in healthy shape). Breakfast was horrible: three waffle makers(why?!), some cereal, microwaveable Jimmy Dean sandwiches instead of ANY hot dishes, Great Valley granola bars, a thermos of coffee, decaf, and coffee-flavored hot water for Lipton tea. Lovely staff, but not enough for us to come back again.

Reviewed on Jul 13, 2025

Ballpark Apartments by Barsala

Ballpark Apartments by Barsala

4 out of 5
Downtown St. Louis
Save 100% on your flight
per person
Aug 15 - Aug 17
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
7.4/10 Good! (9 reviews)
It's a great location, right across from the Ballpark. It is a fairly spartan apartment set-up, with concrete floors.. a little surprising? Parking is on the street or in a pay lot.

Reviewed on Jun 8, 2025

Lodge Of Four Seasons Golf Resort, Marina & Spa

Lodge Of Four Seasons Golf Resort, Marina & Spa

4 out of 5
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
7.2/10 Good! (1,013 reviews)
We enjoyed the resort with plenty to do without having to leave the premises. It's a little "time dated" but we enjoyed that as well. The lady at the desk said they were going to have a lot of work done in 2 weeks to "refresh" the whole lodge. The food was good, the Japanese garden was beautiful, we enjoyed the pool, and the scene of the Lake was gorgeous! We enjoyed sitting on the balcony of our room & watching the boaters on the Lake. My wife had both a pedicure & a manicure & she was very happy with the lady who took care of her. We have already shared our experience with some friends! (Oh yeah, we were celebrating our 40th Anniversary.)

Reviewed on Jul 14, 2025

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.4/10 Very Good! (1,000 reviews)
Pool area and service was great !!!!

Reviewed on Jul 14, 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
$89 nightly
The price is $99 total per night from Jul 27 to Jul 28
$99 total
Jul 27 - Jul 28
Total includes taxes and fees
9.2/10 Wonderful! (537 reviews)
"Very clean and friendly staff. Will stay here again"

Reviewed on Jul 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 Jul 16 to Jul 17
$85 total
Jul 16 - Jul 17
Total includes taxes and fees
8.4/10 Very Good! (671 reviews)
Hot & Humid week = muggy room
"The hallways were pretty warm. It was a hot and humid week, the room were humid and had to run the A/C fan at 66 to try to dry it out a bit. It was ok for room comfort."

Reviewed on Jul 6, 2025

Best Western Jacksonville Inn
Baymont by Wyndham Jacksonville
Baymont by Wyndham Jacksonville
2.5 out of 5
1914 Southbrooke Road, Jacksonville, IL
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $66 total per night from Jul 21 to Jul 22
$66 total
Jul 21 - Jul 22
Total includes taxes and fees
7/10 Good! (808 reviews)
"Newly renovated. Attentive friendly staff."

Reviewed on Jun 25, 2025

Baymont by Wyndham Jacksonville
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.

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 $332 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.