Winchester Vacations from $214

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Graduate by Hilton Cincinnati

Graduate by Hilton Cincinnati

4 out of 5
Corryville
Price was $276, price is now $214 per person
$214
per person
Feb 27 - Mar 1
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Cincinnati (CVG)
9.4/10 Exceptional! (1,360 reviews)
The check in was quick, easy and the staff was friendly. The room was clean and beds were comfortable. Easy to get to the children’s hospital so we will Definitely stay again!

Reviewed on Jan 23, 2026

Hilton Cincinnati Netherland Plaza

Hilton Cincinnati Netherland Plaza

4 out of 5
Downtown Cincinnati
Save 100% on your flight
Price was $746, price is now $533 per person
$533
per person
Mar 27 - Apr 1
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Cincinnati (CVG)
8/10 Very Good! (1,268 reviews)
Clean room and friendly staff

Reviewed on Jan 16, 2026

Quality Inn & Suites Cincinnati Uptown Norwood

Quality Inn & Suites Cincinnati Uptown Norwood

2.5 out of 5
Price was $309, price is now $235 per person
$235
per person
Feb 22 - Feb 27
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Cincinnati (CVG)
5.8/10 (628 reviews)
The room was clean the lobby and breakfast area was clean. The hotel itself and even the room had like a musty smell you could tell they were trying to clean it up by the smell of the cleaning materials but all in all we got a good night sleep and that was our goal for the one evening

Reviewed on Dec 7, 2025

The Lytle Park Hotel, Autograph Collection

The Lytle Park Hotel, Autograph Collection

4.5 out of 5
Downtown Cincinnati
Save 100% on your flight
Price was $524, price is now $408 per person
$408
per person
Feb 27 - Mar 1
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Cincinnati (CVG)
9.6/10 Exceptional! (251 reviews)
Beautiful and tidy place! Service was first class!!

Reviewed on Jan 13, 2026

WoodSpring Suites Cincinnati Fairfield

WoodSpring Suites Cincinnati Fairfield

2.5 out of 5
Price was $280, price is now $220 per person
$220
per person
Feb 22 - Feb 27
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Cincinnati (CVG)
5.4/10 (527 reviews)
Quiet clean easy check in

Reviewed on Dec 4, 2025

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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 OH
10/10 Exceptional! (277 reviews)
Cabin was nice and clean and well stocked. Loved that all rooms are on the same level.

Reviewed on Dec 9, 2025

Get rates
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
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 $97 total per night from Feb 8 to Feb 9
$97 total
Feb 8 - Feb 9
Total with taxes and fees
7.2/10 Good! (552 reviews)
Nice room With jacuzzi tub.

Reviewed on Dec 28, 2025

Countryside Inn & Suites
Beverly hills inn

Beverly hills inn

2.5 out of 5
1830 U.S. 52 Aberdeen OH
Fully refundableReserve now, pay when you stay
$48 nightly
The price is $53 total per night from Jan 25 to Jan 26
$53 total
Jan 25 - Jan 26
Total with taxes and fees
8.4/10 Very Good! (156 reviews)
Everything good

Reviewed on Jan 16, 2026

Beverly hills inn
See all 146 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
1,050
Max Temp Winter
40ºF
Max Temp Summer
80ºF

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Frequently asked questions

How much does a Winchester vacation package cost?
Offering excellent value package deals from $214 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.

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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.