Winchester Vacations from $174

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Your Winchester Vacation

History, cuisine, art and more … There's so much to discover with a Winchester vacation package. And with the ability to customize your city break, it's guaranteed to be one you won't forget. Eager to start exploring your surroundings? Fair Hill State Natural Resources Management Area, Patriots Glen Golf Club and East Meadow Park are among the leading places to visit during your trip to Winchester. Your dream Winchester vacation is a couple of clicks away. Search accommodations, flights and more on Expedia for an adventure that's tailored to suit your style.

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree Hotel Baltimore - BWI Airport

DoubleTree Hotel Baltimore - BWI Airport

4 out of 5
Save 100% on your flight
Price was $243, price is now $174 per person
$174
per person
Apr 16 - Apr 19
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,247 reviews)
Friendly staff, and clean rooms

Reviewed on Feb 1, 2026

Hyatt House BWI Airport Baltimore

Hyatt House BWI Airport Baltimore

3 out of 5
Save 100% on your flight
Price was $290, price is now $186 per person
$186
per person
Apr 16 - Apr 19
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (665 reviews)
Great place, great staff and breakfast. Can’t wait to stay again!

Reviewed on Feb 1, 2026

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $387, price is now $260 per person
$260
per person
Apr 16 - Apr 19
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (2,362 reviews)
Yes and excellent staff

Reviewed on Jan 30, 2026

The Westin Baltimore Washington Airport - BWI

The Westin Baltimore Washington Airport - BWI

4 out of 5
Save 100% on your flight
Price was $324, price is now $226 per person
$226
per person
Apr 16 - Apr 19
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,082 reviews)
Room clean , staff very friendly and didn’t approve of the fact parking had to paid daily

Reviewed on Feb 1, 2026

Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

4 out of 5
Inner Harbor
Save 100% on your flight
Price was $524, price is now $367 per person
$367
per person
Apr 16 - Apr 19
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (2,459 reviews)
Clean room and friendly front desk representatives.

Reviewed on Jan 23, 2026

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Discover the most popular places to visit in Winchester

Fair Hill State Natural Resources Management Area

Explore the great outdoors at Fair Hill State Natural Resources Management Area, a lovely green space in Elkton. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Fair Hill State Natural Resources Management Area

Union Hospital

Though Union Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Elkton while you are here.

Union Hospital

Patriots Glen Golf Club

Enjoy a round of golf in Elkton at Patriots Glen Golf Club. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Patriots Glen Golf Club

Winchester Hotel Deals

Sheraton Suites Wilmington Downtown

Sheraton Suites Wilmington Downtown

3.5 out of 5
422 Delaware Ave Wilmington DE
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $140 total per night from Feb 6 to Feb 7
$140 total
Feb 6 - Feb 7
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Always the best place with early check in. Clean and cozy with super awesome customer service.

Reviewed on Jan 20, 2026

Sheraton Suites Wilmington Downtown
Embassy Suites by Hilton Newark Wilmington South

Embassy Suites by Hilton Newark Wilmington South

3.5 out of 5
654 S College Ave Newark DE
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $113 total per night from Feb 8 to Feb 9
$113 total
Feb 8 - Feb 9
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
Yes

Reviewed on Jan 25, 2026

Embassy Suites by Hilton Newark Wilmington South
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
$80 nightly
The price is $89 total per night from Feb 3 to Feb 4
$89 total
Feb 3 - Feb 4
Total with taxes and fees
7.6/10 Good! (1,254 reviews)
Perfect

Reviewed on Jan 30, 2026

Sonesta Select Newark Christiana Mall
See all 652 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
Closest Airport
Wilmington, DE (ILG-New Castle)
Top Sights
Historical Society of Cecil County, Fair Hill State Natural Resources Management Area and Patriots Glen Golf Club

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Frequently asked questions

How much does a Winchester vacation package cost?
Offering great value package deals from $174 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?
If you're hoping to book a cheap Winchester vacation package, consider planning a trip in November, December and January. You'll generally find better prices on accommodations and flights during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Winchester?
With a well-organized travel plan, you can easily tick off the main Winchester attractions in a handful of days. But if you prefer to explore off the beaten track or go on day tours, consider booking your Winchester vacation for longer.
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.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
If you're anything like us, you love going away but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Winchester break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.