Winchester Vacations from $384

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
The Cincinnatian Hotel Curio Collection by Hilton

The Cincinnatian Hotel Curio Collection by Hilton

4 out of 5
Downtown Cincinnati
Price was $487, price is now $384 per person
$384
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cincinnati (CVG)
7.6/10 Good! (1,005 reviews)
Customer service from onsite staff was the best this hotel had to offer. Everyone was pleasant and accommodating. The hotel could use a maintenance overhaul. The rooms were very much showing their age with beat up floors, stained furniture, chipped and worn down paint. The cleanliness was not great, noticeable dust in corners of the room and places the top of the toilet paper holder (which was also falling off the wall). Hotel lobby, bar, and coffee shop are nice. Location is great, however, the abandoned building next door is being worked on so construction work begins at 6am! Nice and noisy! I wouldn't expect it to be super quiet given that it's in the heart of downtown, but the construction definitely makes it unpleasant.

Reviewed on Oct 8, 2025

voco The Clair Cincinnati Downtown by IHG

voco The Clair Cincinnati Downtown by IHG

3 out of 5
Downtown Cincinnati
Price was $821, price is now $616 per person
$616
per person
Dec 29 - Jan 2
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Cincinnati (CVG)
9.2/10 Wonderful! (1,013 reviews)
Nice room, very updated hotel.

Reviewed on Oct 12, 2025

Hyatt Regency Cincinnati

Hyatt Regency Cincinnati

4 out of 5
Downtown Cincinnati
Price was $820, price is now $629 per person
$629
per person
Dec 29 - Jan 2
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Cincinnati (CVG)
9/10 Wonderful! (1,539 reviews)
Loved the hotel! Great location and very friendly staff.

Reviewed on Oct 12, 2025

Hotel Covington Cincinnati Riverfront

Hotel Covington Cincinnati Riverfront

4 out of 5
Price was $998, price is now $782 per person
$782
per person
Dec 29 - Jan 2
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Cincinnati (CVG)
9.6/10 Exceptional! (1,004 reviews)
Love this hotel. 5 STARS

Reviewed on Oct 7, 2025

Embassy Suites by Hilton Cincinnati RiverCenter

Embassy Suites by Hilton Cincinnati RiverCenter

3.5 out of 5
Price was $788, price is now $630 per person
$630
per person
Dec 29 - Jan 2
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Cincinnati (CVG)
7.4/10 Good! (1,008 reviews)
There was no shampoo in the shower

Reviewed on Oct 11, 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! (273 reviews)
"My husband and I wanted a getaway and this cabin was perfect. It was clean, pretty and had everything we could possibly need. We enjoyed fishing in the large pond and our black lab really loved soaking in it while we fished. We will definitely be back."

Reviewed on Sep 21, 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
$47 nightly
The price is $53 total per night from Nov 11 to Nov 12
$53 total
Nov 11 - Nov 12
Total with taxes and fees
8.6/10 Excellent! (128 reviews)
"Nice atmosphere. I plan to visit again in summer. The pool looked fun"

Reviewed on Oct 8, 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 $97 total per night from Oct 27 to Oct 28
$97 total
Oct 27 - Oct 28
Total with taxes and fees
7.2/10 Good! (534 reviews)
"The room was clean. Everything worked in the room. Staff was very polite"

Reviewed on Sep 28, 2025

Countryside Inn & Suites
See all 145 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.

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 $384 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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.