Winchester Vacations from ￥206,212

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The Latest Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ashley Quarters Hotel Cincinnati Airport

Ashley Quarters Hotel Cincinnati Airport

2.5 out of 5
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip flight included
Nagoya (NGO) to Cincinnati (CVG)
9/10 Wonderful! (822 reviews)
Our room was nice & clean—but not as fancy as featured photo. All was good—would definitely stay again

Reviewed on Jun 19, 2025

The Cincinnatian Hotel Curio Collection by Hilton

The Cincinnatian Hotel Curio Collection by Hilton

4 out of 5
Downtown Cincinnati
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip flight included
Nagoya (NGO) to Cincinnati (CVG)
7.6/10 Good! (1,000 reviews)
We had a great stay here. Good location, great staff, comfortable bed. It’s an older hotel so it has some charm but our room was updated.

Reviewed on Jun 23, 2025

Hotel Covington Cincinnati Riverfront

Hotel Covington Cincinnati Riverfront

4 out of 5
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip flight included
Nagoya (NGO) to Cincinnati (CVG)
9.6/10 Exceptional! (1,001 reviews)
Very clean, comfortable and well appointed I wish room service was available after 9pm Convenient location Very nice hotel for the money

Reviewed on Jun 24, 2025

Hilton Cincinnati Netherland Plaza

Hilton Cincinnati Netherland Plaza

4 out of 5
Downtown Cincinnati
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip flight included
Nagoya (NGO) to Cincinnati (CVG)
7.8/10 Good! (1,007 reviews)
It’s a cool place was probably amazing 60 years ago but by today’s standards it needs some freshening up. The art deco is so cool. Maintaining this 30 story behemoth must cost a fortune The staff - 10 stars. Helpful, polite and welcoming.

Reviewed on Jun 24, 2025

21c Museum Hotel Cincinnati

21c Museum Hotel Cincinnati

4.5 out of 5
Downtown Cincinnati
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip flight included
Nagoya (NGO) to Cincinnati (CVG)
8.8/10 Excellent! (1,002 reviews)
Great service and friendly employees!

Reviewed on Jun 25, 2025

Find the Best Winchester Vacation Packages

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)
Peaceful
"Very clean, peaceful, quiet."

Reviewed on Jun 23, 2025

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
The price is ￥12,500 per night from Jul 9 to Jul 10
￥12,500
￥14,156 total
Jul 9 - Jul 10
includes taxes & fees
7/10 Good! (499 reviews)
"The stay was great"

Reviewed on Jun 21, 2025

Countryside Inn & Suites
Beverly hills inn
Beverly hills inn
2.5 out of 5
1830 U.S. 52, Aberdeen, OH
Fully refundableReserve now, pay when you stay
The price is ￥6,521 per night from Jun 26 to Jun 27
￥6,521
￥7,254 total
Jun 26 - Jun 27
includes taxes & fees
8.8/10 Excellent! (43 reviews)
"Every one at this hotel was nice friendly and accommodating"

Reviewed on Jun 22, 2025

Beverly hills inn
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.

Frequently asked questions

How much does a Winchester vacation package cost?
Offering excellent value package deals from ￥206,212 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?
The off-season is the best time to travel to Winchester if you're trying to save. Another tip for finding cheap Winchester vacation packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Winchester?
Usually, a handful of days is enough to go to the top attractions during your Winchester vacation. But if you want to have more time to rest or take day trips, think about extending your trip.
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.
How to plan a trip to Winchester?

  1. Choose when to get away: Check your diary and get packing. Your favorite season and the activities on offer will also help you decide when to vacation in Winchester.
  2. Figure out your budget: Ensure you have enough money to pay for everything from meals and transportation to flights and activities. Your hotel will probably be the biggest expense during your trip to Winchester.
  3. Decide your trip length: Consider how much time you want to spend discovering Winchester. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Winchester vacation package that brings all your bookings together.

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