Winchester Historic District Vacation Packages for 2025

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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
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
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
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
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 breakfast and the helpful staff in our reviews. ...
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 ...
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 ...
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
25.73 km from Winchester Historic District
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 ...
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 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 ...
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

3 out of 5
300 Marriott Drive, Winchester, VA
2.91 km from Winchester Historic District
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise 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
Stay at this 4-star 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

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
7.51 km from Winchester Historic District
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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 ...
Rodeway Inn & Suites - Charles Town, WV

Rodeway Inn & Suites - Charles Town, WV

2 out of 5
741 E Washington St, Charles Town, WV
29.85 km from Winchester Historic District
Book a stay at this business-friendly motel in Charles Town. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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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.

Spirit Airlines
Wed, Oct 22 - Sat, Nov 8
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$86 Roundtrip, found 3 days ago
$86
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Oct 22 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Nov 8, priced at $86 found 3 days ago
Frontier Airlines
Sat, Nov 1 - Sun, Nov 16
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$90 Roundtrip, found 1 day ago
$90
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 1 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Nov 16, priced at $90 found 1 day ago
American Airlines
Sat, Nov 1 - Tue, Nov 4
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Nov 1 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Tue, Nov 4, priced at $137 found 1 day ago
Delta
Tue, Nov 18 - Mon, Nov 24
MIA
Miami Intl.
DCA
Ronald Reagan Washington National
$189 Roundtrip, found 4 days ago
$189
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Nov 18 from Miami Intl. to Ronald Reagan Washington National, returning Mon, Nov 24, priced at $189 found 4 days ago
JetBlue Airways
Thu, Nov 6 - Mon, Nov 10
TPA
Tampa Intl.
DCA
Ronald Reagan Washington National
$196 Roundtrip, found 4 days ago
$196
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Thu, Nov 6 from Tampa Intl. to Ronald Reagan Washington National, returning Mon, Nov 10, priced at $196 found 4 days ago