Winchester Vacations from $367

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Cincinnati Netherland Plaza
Belterra Casino Resort
21c Museum Hotel Cincinnati
Hyatt Regency Cincinnati
The Cincinnatian Hotel Curio Collection by Hilton
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Winchester Hotel Deals

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Winchester
10/10 Exceptional! (269 reviews)
Great place
"Would definitely come back"

Reviewed on Aug 11, 2025

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Beverly hills inn

Beverly hills inn

2.5 out of 5
1830 U.S. 52, Aberdeen, OH
Fully refundableReserve now, pay when you stay
$50 nightly
The price is $56 total per night from Aug 29 to Aug 30
$56 total
Aug 29 - Aug 30
Total with taxes and fees
8.6/10 Excellent! (110 reviews)
"Older motel but it's clean and safe."

Reviewed on Aug 23, 2025

Beverly hills inn
Countryside Inn & Suites

Countryside Inn & Suites

2.5 out of 5
100 Leininger Street, Mount Orab, OH
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $98 total per night from Sep 11 to Sep 12
$98 total
Sep 11 - Sep 12
Total with taxes and fees
7/10 Good! (525 reviews)
Perfect stopover
"This is a very convenient, easily accessible, reasonably priced, property run by a hands on staff working hard to catch up on some deferred maintenance. Lots of food options nearby. Overall, I would stay there again if in the area."

Reviewed on Aug 11, 2025

Countryside Inn & Suites
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.

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Frequently asked questions

How much does a Winchester vacation package cost?
Offering excellent value package deals from $367 on Expedia, you'll be thrilled with how little a vacation to Winchester costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Winchester?
If you'd like to score a cheap Winchester vacation package, consider visiting in January, February and April. You'll usually find better rates on accommodations and flights during these months — ideal for budget-conscious travelers.
How many days is enough for Winchester?
The ideal duration for your Winchester vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to tick off all the leading attractions and discover some hidden gems along the way.
How to find the best Winchester package deals?
Landing a cheap Winchester package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Winchester package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging stays and flights individually. Better still, you can tailor your Winchester getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Winchester?
Score amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Winchester break.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Jet off on your perfect escape to Winchester with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for payday — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snag great deals while they last.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.