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 ...
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 ...
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. ...
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 ...
Comfort Inn & Suites

Comfort Inn & Suites

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 ...
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 ...
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 ...
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 ...
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 ...
Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park

2.5 out of 5
10 S Commerce Ave, Front Royal, VA
29.85 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 helpful staff 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 ...
Sleep Inn & Suites

Sleep Inn & Suites

2.5 out of 5
140 Costello Dr, Winchester, VA
3.24 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 ...
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 ...
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr, Winchester, VA
2.11 km from Winchester Historic District
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
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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
Sat, Aug 16 - Sat, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$70 Roundtrip, found 6 days ago
$70
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Aug 23, priced at $70 found 6 days ago
Spirit Airlines
Sat, Sep 13 - Tue, Sep 23
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$90 Roundtrip, found 4 days ago
$90
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, Sep 13 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 23, priced at $90 found 4 days ago
Delta
Wed, Sep 17 - Mon, Sep 29
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$114 Roundtrip, found 4 days ago
$114
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Sep 17 from Logan Intl. to Ronald Reagan Washington National, returning Mon, Sep 29, priced at $114 found 4 days ago
United
Wed, Nov 12 - Thu, Nov 13
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$132 Roundtrip, found 6 days ago
$132
Roundtrip
found 6 days ago
Select United flight, departing Wed, Nov 12 from Orlando Intl. to Washington Dulles Intl., returning Thu, Nov 13, priced at $132 found 6 days ago
American Airlines
Tue, Oct 7 - Tue, Oct 14
MIA
Miami Intl.
DCA
Ronald Reagan Washington National
$147 Roundtrip, found 5 days ago
$147
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Oct 7 from Miami Intl. to Ronald Reagan Washington National, returning Tue, Oct 14, priced at $147 found 5 days ago