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

Hilton Cincinnati Netherland Plaza

4 out of 5
Downtown Cincinnati
Price was $509, price is now $367 per person
$367
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
7.8/10 Good! (1,145 reviews)
Great old hotel. The building itself is beautiful old architecture but the age shows. Hallway carpets need to be cleaned, but overall a pleasant stay.

Reviewed on Aug 26, 2025

Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
Save 100% on your flight
Price was $734, price is now $511 per person
$511
per person
Oct 12 - Oct 17
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
8.4/10 Very Good! (1,000 reviews)
Enjoyed everything except the bathroom. No vent fan in the bathroom. Steamed up badly when showering. Service was good at the bar in the Stadium Sports Bar but it was very slow if seated at a table.

Reviewed on Aug 26, 2025

21c Museum Hotel Cincinnati

21c Museum Hotel Cincinnati

4.5 out of 5
Downtown Cincinnati
Save 100% on your flight
Price was $761, price is now $545 per person
$545
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
8.8/10 Excellent! (1,010 reviews)
The hotel was a museum

Reviewed on Aug 19, 2025

Hyatt Regency Cincinnati

Hyatt Regency Cincinnati

4 out of 5
Downtown Cincinnati
Save 100% on your flight
Price was $771, price is now $552 per person
$552
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Cincinnati (CVG)
9/10 Wonderful! (1,497 reviews)
I had an amazing stay here! The staff were amazing! This is my first trip to Cincinnati and I loved every bit of it, but the staff here made it that much better! Special shout out to Brandon, Scott, and my beautiful waitress! I am not going to butcher her name, but she was very attentive, personable, and kind. The valet staff were all so courteous! I just knew Adam got sick of me going to get my keys every 5 minutes, but he was so pleasant anyway. All in all, great place to stay and the people are amazing.

Reviewed on Aug 25, 2025

The Cincinnatian Hotel Curio Collection by Hilton

The Cincinnatian Hotel Curio Collection by Hilton

4 out of 5
Downtown Cincinnati
Save 100% on your flight
Price was $641, price is now $460 per person
$460
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
7.6/10 Good! (1,002 reviews)
It’s a beautiful hotel, I just wish we could have stayed longer.

Reviewed on Aug 21, 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! (269 reviews)
Great place
"Would definitely come back"

Reviewed on Aug 11, 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 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
See all 144 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.

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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.