Winchester Vacations from $255
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Your Winchester Vacation
The rich history and small-town feel are just the start of the things Winchester has on offer. Experience the best of this city your way with a tailor-made Winchester vacation package. You'll want to do some exploring during your trip to Winchester. Find time for big-name attractions such as Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Winchester vacation is easy with Expedia.
The Latest Winchester vacation packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Laurel
West Laurel
Save 100% on your flight
Price was $438, price is now $255 per person
$255
per person
Dec 5 - Dec 10
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,006 reviews)
We chose this hotel for its convenient on/off location to I 95. But it turned out to be a friendly, quiet, clean and comfortable stay. Loved the Tex-Mex restaurant and the breakfast buffet too.
Reviewed on Oct 3, 2025
InterContinental Washington D.C. - The Wharf by IHG
The Wharf
Save 100% on your flight
Price was $1,277, price is now $674 per person
$674
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
9.4/10 Exceptional! (1,010 reviews)
The property was beautiful. The staff was amazing and the area is so easy to get around plenty of dining and entertainment options.
Reviewed on Oct 2, 2025
Graduate by Hilton Annapolis
Save 100% on your flight
Price was $807, price is now $491 per person
$491
per person
Nov 6 - Nov 9
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,008 reviews)
Very rude waitress at restaurant, very aloof and disinterested food and beverage manager. No compensation for disrespect and uncomfortable situation in restaurant. Otherwise, very comfortable room and pleasant front desk staff and valet.
Reviewed on Oct 3, 2025
Pier 5 Hotel Baltimore
Inner Harbor
Save 100% on your flight
Price was $495, price is now $306 per person
$306
per person
Dec 5 - Dec 8
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (741 reviews)
Full array of places to eat and drink. Right next to the Pier 6 concert venue. Harbor is beautiful.
Reviewed on Oct 1, 2025
Historic Inns of Annapolis
Historic District
Save 100% on your flight
Price was $649, price is now $402 per person
$402
per person
Nov 6 - Nov 9
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,825 reviews)
Beautiful hotel in the heart of Annapolis. Lots of charm
Reviewed on Oct 3, 2025
Discover the most popular places to visit in Winchester
Museum of the Shenandoah Valley
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Winchester Medical Center
Though Winchester Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here.
Winchester Hotel Deals
Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive, Winchester, VA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $120 total per night from Oct 13 to Oct 14
$120 total
Oct 13 - Oct 14
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
"Clean and inviting!!! Loved the cookie snack!"
Reviewed on Oct 3, 2025
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $118 total per night from Nov 2 to Nov 3
$118 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (2,158 reviews)
"Convenient off I-81, clean, quiet,nice warm breakfast, even great dark roast coffee. Will definitely make this a stop on our way south annually"
Reviewed on Oct 1, 2025
Travelodge by Wyndham Winchester
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $75 total per night from Nov 2 to Nov 3
$75 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (1,100 reviews)
"Good no frills hotel for an overnight stay. Easy off/on Interstate. Room was clean, bed comfotable, breakfast fine (make your own waffles!), staff very friendly. We had a nice quiet night & would stay again."
Reviewed on Sep 27, 2025
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.
Winchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 27,300 |
Max Temp Winter | 40ºF |
Max Temp Summer | 85ºF |
Top Sights | Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theater |
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- Hotels near Winchester-Frederick County Convention & Visitors Bureau
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- Car rental Winchester Airport (WGO)
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
