Winchester Vacations from $400

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Cincinnati (CVG)
8.4/10 Very Good! (1,002 reviews)
Needs to be renovated

Reviewed on May 28, 2025

Barsala At The Village At Stetson Square

Barsala At The Village At Stetson Square

4 out of 5
Corryville
per person
Aug 7 - Aug 10
found 18 hours ago
Roundtrip non-stop flight included
New York (LGA) to Cincinnati (CVG)
7.2/10 Good! (7 reviews)
It was clean and quiet. The staff checked in on me but without pressure. Really enjoyed my stay and check out was really easy.

Reviewed on Apr 28, 2025

The Cincinnatian Hotel Curio Collection by Hilton

The Cincinnatian Hotel Curio Collection by Hilton

4 out of 5
Downtown Cincinnati
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
7.6/10 Good! (1,000 reviews)
The lobby was very nice and clean. However, the toilet in our room was not installed properly and was very wobbly. The room seemed a bit worn.

Reviewed on Jun 27, 2025

Wingate by Wyndham - Cincinnati - Blue Ash

Wingate by Wyndham - Cincinnati - Blue Ash

3 out of 5
per person
Aug 14 - Aug 17
found 19 hours ago
Roundtrip flight included
New York (LGA) to Cincinnati (CVG)
8.8/10 Excellent! (1,001 reviews)
I liked that there was an office complex behind the hotel which made a safe place to go for a walk.

Reviewed on Jun 15, 2025

Hyatt Place Cincinnati/Blue Ash

Hyatt Place Cincinnati/Blue Ash

3 out of 5
per person
Aug 14 - Aug 17
found 19 hours ago
Roundtrip flight included
New York (LGA) to Cincinnati (CVG)
7.8/10 Good! (1,006 reviews)
Great value, hotel service

Reviewed on Jul 1, 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
10/10 Exceptional! (264 reviews)
Beautiful cabin
"Had a great stay. Cabin is awesome and very clean. Was a little difficult finding the pond but Jim answered my txt quickly and found it no problem. Fishing was ok but the weather was very hot during my stay. There’s quite a bit to do in the area. Very nice scenery. Would be a great deer hunting cabin ..."

Reviewed on Jun 26, 2025

Get rates
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 Jul 6 to Jul 7
$56 total
Jul 6 - Jul 7
Total includes taxes and fees
8.6/10 Excellent! (50 reviews)
"Clean room and area. Low prices. Friendly associates. Restaurant close by. Close to Maysville, KY and Ripley, Ohio. They could use some towel racks."

Reviewed on Jul 2, 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 Jul 20 to Jul 21
$98 total
Jul 20 - Jul 21
Total includes taxes and fees
7/10 Good! (506 reviews)
Road trip hotel
"It's a nice place, clean and quiet. For a night in a RT, it's perfect."

Reviewed on Jun 30, 2025

Countryside Inn & Suites
See all 143 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 $400 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.