Winchester Vacations from $330

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Cincinnati RiverCenter

Embassy Suites by Hilton Cincinnati RiverCenter

3.5 out of 5
Price was $452, price is now $330 per person
$330
per person
May 11 - May 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
7.4/10 Good! (1,005 reviews)
The room was comfortable.. Front desk staff friendly.. nice to have a free glass of wine

Reviewed on Mar 1, 2026

Siegel Select Cincinnati Sharonville

Siegel Select Cincinnati Sharonville

2 out of 5
Price was $582, price is now $411 per person
$411
per person
Apr 14 - Apr 17
found 1 day ago
Roundtrip flight included
New York (NYC) to Cincinnati (CVG)
3.6/10 (5 reviews)
Hotel Covington Cincinnati Riverfront

Hotel Covington Cincinnati Riverfront

4 out of 5
Save 100% on your flight
Price was $629, price is now $456 per person
$456
per person
May 11 - May 14
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
9.6/10 Exceptional! (1,002 reviews)
Amazing property. Great staff wonderful bar and restaurant. Beautiful you can’t go wrong booking here.

Reviewed on Mar 2, 2026

Great Wolf Lodge Cincinnati/Mason

Great Wolf Lodge Cincinnati/Mason

3.5 out of 5
Save 100% on your flight
Price was $489, price is now $356 per person
$356
per person
May 11 - May 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Cincinnati (CVG)
8.6/10 Excellent! (1,002 reviews)
Hotel and waterpark was great. Wasn't impressed with having to pay $20 a day to park though

Reviewed on Feb 22, 2026

Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
Price was $541, price is now $395 per person
$395
per person
May 20 - May 23
found 1 day ago
Roundtrip flight included
Houston (IAH) to Cincinnati (CVG)
8.6/10 Excellent! (1,003 reviews)
The resort was gorgeous, and the rooms were amazing also. There wasn't as many slots as I would expect but loved the table games!

Reviewed on Feb 22, 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
Get rates
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
French Quarter Inn

French Quarter Inn

3 out of 5
25 East McDonald Parkway Maysville KY
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $122 total per night from Mar 5 to Mar 6
$122 total
Mar 5 - Mar 6
Total with taxes and fees
8.8/10 Excellent! (765 reviews)
Staff was very helpful and pleasant. Bathroom not the cleanest but otherwise room was clean and comfortable

Reviewed on Mar 2, 2026

French Quarter 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 $97 total per night from Mar 18 to Mar 19
$97 total
Mar 18 - Mar 19
Total with taxes and fees
7.2/10 Good! (558 reviews)
Extra charges that shouldnt of been added plus bugs in room

Reviewed on Feb 17, 2026

Countryside Inn & Suites
See all 147 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 $330 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.