Winchester Vacations from $367

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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.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $643, price is now $367 per person
$367
per person
Jul 24 - Jul 29
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,001 reviews)
Parking detached from the actual hotel. Location setting is excellent and close to many shops and local

Reviewed on May 12, 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $833, price is now $456 per person
$456
per person
Jul 24 - Jul 29
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,184 reviews)
Everything was perfect, a very nice surprise.

Reviewed on May 8, 2026

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 $714, price is now $406 per person
$406
per person
Jul 24 - Jul 29
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,000 reviews)
Great staff and a he beds were very comfortable

Reviewed on Apr 21, 2026

Kimpton Banneker Hotel by IHG

Kimpton Banneker Hotel by IHG

4.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $724, price is now $427 per person
$427
per person
Jul 24 - Jul 29
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (799 reviews)
Room was spacious and very comfortable, and very clean. Bed and pillows very comfy. As other reviews noted, water pressure can be an issue, but was manageable. Disappointing not to have in room coffee, as i have no desire to go to the lobby in pjs for coffee. Room service was quick and well done, in-house restaurant was also very good and the hotel offered a free drink and 15% off which was a nice surprise. My only complaint was the morning noise. My room was on the back of the hotel, top floor, and i was awakened both mornings with garbage trucks, beeping delivery trucks, and construction noise that echoed very loudly all the way up 10 floors. If you're a business traveler up early maybe a non issue but there was definitely no sleeping in.

Reviewed on May 13, 2026

Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

5 out of 5
Northwest
Save 100% on your flight
Price was $1,162, price is now $705 per person
$705
per person
Jul 24 - Jul 29
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,004 reviews)
If you're looking at this hotel, go ahead and book it! Not only is it luxurious and friendly, but you'll find at least 5 taxis by it at any time (a definite plus when certain Metro lines are being repaired). Added bonus: the signature house fragrance is unspeakably delicious. You will love your stay here!

Reviewed on Apr 29, 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

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

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
$135 nightly
The price is $149 total per night from Jun 7 to Jun 8
$149 total
Jun 7 - Jun 8
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
this is a nice property. Clean and comfortable.

Reviewed on May 9, 2026

Sheraton Suites Wilmington Downtown
Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

2 out of 5
1240 Chesapeke Overlook Parkway Perryville MD
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $223 total per night from May 17 to May 18
$223 total
May 17 - May 18
Total with taxes and fees
8.8/10 Excellent! (215 reviews)
Clean night and a good time for the children

Reviewed on May 5, 2026

Great Wolf Lodge Perryville
Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

2.5 out of 5
65 Geoffrey Dr Newark DE
Fully refundable
$67 nightly
The price is $74 total per night from May 25 to May 26
$74 total
May 25 - May 26
Total with taxes and fees
5.6/10 (1,002 reviews)
I really wanted to give the Quality Inn a chance even after reading the poor reviews, but I really was disappointed by my stay there. This facility really needs updating, which would include a deep cleaning of the inside and outside. I received no room service during my stay so had to go to the lobby ...

Reviewed on May 13, 2026

Quality Inn Newark - Wilmington
See all 607 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 $367 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.