Winchester Vacations from $208

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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.
Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Save 100% on your flight
Price was $316, price is now $208 per person
$208
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,001 reviews)
The hotel is showing its age and likewise the pool area which used to be its best part in winter

Reviewed on Dec 6, 2025

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $929, price is now $573 per person
$573
per person
Jan 11 - Jan 18
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
8.6/10 Excellent! (1,008 reviews)
I recommend this hotel to anybody who wants to have a combination of great location, amenities and services, cleanliness, comfort, and staff.

Reviewed on Dec 7, 2025

Hampton Inn & Suites Washington DC-Navy Yard

Hampton Inn & Suites Washington DC-Navy Yard

3 out of 5
Navy Yard
Save 100% on your flight
Price was $331, price is now $211 per person
$211
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,004 reviews)
Very good property, good rates

Reviewed on Dec 7, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $702, price is now $457 per person
$457
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Miami (MIA) to Baltimore (BWI)
8.2/10 Very Good! (1,002 reviews)
The staff was outstanding—everyone from the front desk to the room cleaning & maintenance! The campus and environment was also very clean and outstanding. I’ll only stay at Kellogg on my visits to Washington DC!!

Reviewed on Nov 25, 2025

Canopy by Hilton Washington DC Bethesda North

Canopy by Hilton Washington DC Bethesda North

4 out of 5
Save 100% on your flight
Price was $417, price is now $277 per person
$277
per person
Jan 15 - Jan 18
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
8.8/10 Excellent! (1,002 reviews)
Breakfast menu was fantastic.

Reviewed on Dec 7, 2025

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Discover the most popular places to visit in Winchester

Fair Hill State Natural Resources Management Area

3.5/5(2 reviews)

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

4/5(4 reviews)

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

Historical Society of Cecil County

You can spend time studying the exhibits at Historical Society of Cecil County during your trip to Elkton. While you're here, you can savor the top-notch restaurants.

Historical Society of Cecil County

Winchester Hotel Deals

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
$90 nightly
The price is $100 total per night from Dec 11 to Dec 12
$100 total
Dec 11 - Dec 12
Total with taxes and fees
7.6/10 Good! (1,200 reviews)
My three day stay was great. Staff were really friendly and helpful. My only thing was the hot water was lukewarm and the fold out bed had no sheets on it. I had to go request bedding. I would stay again.

Reviewed on Dec 7, 2025

Sonesta Select Newark Christiana Mall
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
$119 nightly
The price is $131 total per night from Dec 19 to Dec 20
$131 total
Dec 19 - Dec 20
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
Perfect location. Was able to get back-and-forth to the Philadelphia area. The hotels in a prime location, on site parking was available. The hotel room was clean and spacious.

Reviewed on Dec 4, 2025

Sheraton Suites Wilmington Downtown
Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

2.5 out of 5
65 Geoffrey Dr Newark DE
Fully refundableReserve now, pay when you stay
$66 nightly
The price is $73 total per night from Dec 15 to Dec 16
$73 total
Dec 15 - Dec 16
Total with taxes and fees
5/10 (1,004 reviews)
Yes

Reviewed on Dec 2, 2025

Quality Inn Newark - Wilmington
See all 642 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 $208 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.