Winchester Historic District Vacation Packages for 2026

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Top Hotel Deals

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
0.44 km from Winchester Historic District
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East Winchester VA
3.04 km from Winchester Historic District
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 ...
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
4.18 km from Winchester Historic District
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
7.81 km from Winchester Historic District
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 ...
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive Winchester VA
2.21 km from Winchester Historic District
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 out of 5
280 MARKET STREET Winchester VA
5.34 km from Winchester Historic District
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 ...
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
2.99 km from Winchester Historic District
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd Front Royal VA
25.09 km from Winchester Historic District
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 ...
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd Winchester VA
7.51 km from Winchester Historic District
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 ...
Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry

2 out of 5
642 E Washington Street Charles Town WV
29.72 km from Winchester Historic District
Book a stay at this business-friendly hotel in Charles Town. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4 out of 5
111 Hospitality Drive Front Royal VA
21.97 km from Winchester Historic District
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 ...
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
3.35 km from Winchester Historic District
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 ...
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
4.39 km from Winchester Historic District
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. ...
Quality Inn Winchester

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
4.36 km from Winchester Historic District
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 ...
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

3 out of 5
300 Marriott Drive Winchester VA
2.91 km from Winchester Historic District
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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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.

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.

Frontier Airlines
Fri, Dec 12 - Mon, Dec 15
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$50 Roundtrip, found 17 hours ago
$50
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Fri, Dec 12 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Dec 15, priced at $50 found 17 hours ago
JetBlue Airways
Wed, Jan 7 - Thu, Jan 8
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$91 Roundtrip, found 1 day ago
$91
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Jan 7 from Orlando Intl. to Ronald Reagan Washington National, returning Thu, Jan 8, priced at $91 found 1 day ago
Spirit Airlines
Wed, Feb 11 - Wed, Feb 18
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 16 hours ago
$98
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Wed, Feb 11 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Feb 18, priced at $98 found 16 hours ago
Delta
Tue, Jan 6 - Sat, Jan 10
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$117 Roundtrip, found 3 days ago
$117
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jan 6 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sat, Jan 10, priced at $117 found 3 days ago
American Airlines
Mon, Dec 22 - Fri, Dec 26
CLT
Charlotte-Douglas Intl.
DCA
Ronald Reagan Washington National
$204 Roundtrip, found 1 day ago
$204
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Dec 22 from Charlotte-Douglas Intl. to Ronald Reagan Washington National, returning Fri, Dec 26, priced at $204 found 1 day ago