Winchester Historic District Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Top Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Book a stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
Book a stay at this spa hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
Book a stay at this business-friendly hotel in Front Royal. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
DoubleTree by Hilton Front Royal Blue Ridge Shadows
111 Hospitality Drive Front Royal VA
Book a stay at this golf hotel in Front Royal. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff and the clean rooms in our ...
Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Super 8 by Wyndham Front Royal Near Shenandoah National Park
111 South St Front Royal VA
Stay at this hotel in Front Royal. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
Courtyard by Marriott Winchester
300 Marriott Drive Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
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View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Sep 30 - Wed, Oct 7
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$58
Roundtrip
found 6 days ago
Tue, Oct 20 - Tue, Oct 27
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$165
Roundtrip
found 10 hours ago
Tue, Oct 20 - Tue, Nov 3
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$171
Roundtrip
found 7 hours ago
Thu, Oct 29 - Tue, Nov 3
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$183
Roundtrip
found 1 day ago
Best points of interest in Winchester
- Shenandoah Valley Discovery Museum Vacations
- Bright Box Theater Vacations
- Stonewall Jackson's Headquarters Vacations
- Winchester Little Theater Vacations
- Old Court House Civil War Museum Vacations
- Handley Regional Library Vacations
- George Washington's Office Vacations
- Shenandoah National Park Vacations
- Hollywood Casino at Charles Town Races Vacations
- Shenandoah University Vacations
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