Winchester Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Winchester Vacation Packages

Winchester Hotel Deals

Red Roof Inn & Suites Newark - University
Red Roof Inn & Suites Newark - University
2 out of 5
1119 S College Avenue, Newark, DE
Fully refundableReserve now, pay when you stay
The price is ₩105,747 per night from Jul 13 to Jul 14
₩105,747
₩117,381 total
Jul 13 - Jul 14
includes taxes & fees
5.4/10 (1,004 reviews)
"Good stop over a little construction"

Reviewed on Jul 5, 2025

Red Roof Inn & Suites Newark - University
Sonesta Select Newark Christiana Mall
Sonesta Select Newark Christiana Mall
3 out of 5
48 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is ₩138,931 per night from Aug 3 to Aug 4
₩138,931
₩154,214 total
Aug 3 - Aug 4
includes taxes & fees
7.8/10 Good! (1,019 reviews)
"Wonderful clean quiet"

Reviewed on Jul 7, 2025

Sonesta Select Newark Christiana Mall
DoubleTree by Hilton Downtown Wilmington - Legal District
DoubleTree by Hilton Downtown Wilmington - Legal District
4 out of 5
700 N King St, Wilmington, DE
Fully refundableReserve now, pay when you stay
The price is ₩131,926 per night from Jul 31 to Aug 1
₩131,926
₩145,118 total
Jul 31 - Aug 1
includes taxes & fees
7.4/10 Good! (1,000 reviews)
"This hotel is very convenient if you are seeing a show at the Grand Ballroom which is right across the street. It was comfortable and clean and also affordable. The staff was friendly. Would recommend for a quick stopover in the downtown Wilmington area."

Reviewed on Jul 2, 2025

DoubleTree by Hilton Downtown Wilmington - Legal District
See all 614 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.

Discover the most popular places to visit in Winchester

Cow Pond

Commune with nature and explore the great outdoors at Cow Pond during your travels in Elkton. While you're here, you can savor the top-notch restaurants.

Cow Pond

Frequently asked questions

How much does a Winchester vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Winchester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winchester?
You're likely to find lower prices and greater availability in January, February and November. Browse our cheap Winchester vacation packages and you could land some great off-season discounts.
How many days is enough for Winchester?
Usually, a handful of days is enough to tick off the top attractions during your Winchester vacation. However, if you prefer to have more time to rest or go on day trips, think about extending your itinerary.
How to find the best Winchester package deals?
Start your search for a Winchester package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Winchester package deal right away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winchester escape underway.
Is it cheaper to book a Winchester vacation as a package?
You can enjoy significant savings on your Winchester break by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winchester?
If you have your Winchester vacation dates confirmed, book as early as you can to bag some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for traveling on a whim.
How to plan a trip to Winchester?

  1. Choose your dates: What you plan to do in Winchester and your favorite season can help you decide when to go.
  2. Work out your budget: Make sure you have enough money to cover everything from food and transportation to airfares and activities. Your hotel will likely be the biggest expense during your trip to Winchester.
  3. Decide how long to go for: Now that you know more about Winchester, you can work out the ideal length of your break. Create a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalized Winchester vacation package.

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