Winchester Vacations from $352

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express West Cincinnati by IHG

Holiday Inn Express West Cincinnati by IHG

3 out of 5
Dent
Price was $451, price is now $352 per person
$352
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cincinnati (CVG)
8.4/10 Very Good! (1,001 reviews)
The overall experience was great. The staff was extremely friendly and helpful, especially at the reception. However, the experience with the breakfast buffet staff was not as positive—one staff member seemed to watch our every movement, which was off-putting. The hotel itself is nice, but it definitely needs to be revamped, as the furniture and amenities, such as the gym, feel outdated.

Reviewed on May 25, 2026

Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
Price was $976, price is now $679 per person
$679
per person
Jul 20 - Jul 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
8.6/10 Excellent! (1,003 reviews)
The shower curtain leaked all over the floor. Our room was ok.

Reviewed on May 31, 2026

Landing Apartments Near University Of Cincinnati

Landing Apartments Near University Of Cincinnati

4 out of 5
Corryville
Save 100% on your flight
Price was $1,281, price is now $921 per person
$921
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cincinnati (CVG)
10/10 Exceptional! (2 reviews)
The apartment was clean, stylish, and incredibly comfortable. Everything I needed was right there, and the space felt modern and well-maintained. Parking was great! Perfect for our family vacation — we’d definitely come back!

Reviewed on Nov 27, 2025

Cincinnati's Fidelity Hotel

Cincinnati's Fidelity Hotel

3.5 out of 5
Downtown Cincinnati
Save 100% on your flight
Price was $1,581, price is now $1,235 per person
$1,235
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cincinnati (CVG)
No reviews
Holiday Inn Express Hotel & Suites Richwood-Cincinnati South by IHG

Holiday Inn Express Hotel & Suites Richwood-Cincinnati South by IHG

2.5 out of 5
Price was $532, price is now $422 per person
$422
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cincinnati (CVG)
8.8/10 Excellent! (1,005 reviews)
Breakfast was good but tables needed attention more frequently. Nice, quiet, clean room.

Reviewed on May 31, 2026

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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! (281 reviews)
"Very comfortable cabin, loved the layout."

Reviewed on May 25, 2026

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
$80 nightly
The price is $90 total per night from Jun 29 to Jun 30
$90 total
Jun 29 - Jun 30
Total with taxes and fees
7.2/10 Good! (570 reviews)
"I felt the facility was somewhat dirty. The carpets haven’t been cleaned in a very long time. When I got out bed, I put my flip flops to walk about the room because of the dirty carpet. Some updating is needed along with new carpet."

Reviewed on May 31, 2026

Countryside Inn & Suites
Beverly hills inn

Beverly hills inn

2.5 out of 5
1830 U.S. 52 Aberdeen OH
$55 nightly
The price is $61 total per night from Jun 1 to Jun 2
$61 total
Jun 1 - Jun 2
Total with taxes and fees
8.8/10 Excellent! (214 reviews)
"Greatly aging facility. Price was great, but room was not. Fairly clean in main area, but bathroom was not. Decided to forego the restaurant—in general the area was run down enough that we began to not trust the cleanliness."

Reviewed on May 29, 2026

Beverly hills inn
See all 155 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 $352 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.