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 ...
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. ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA

2 out of 5
991 Millwood Pike, Winchester, VA
2.99 km from Winchester Historic District
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
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 ...
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 ...
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 ...
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 ...
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. ...
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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
Mon, Nov 24 - Sun, Dec 7
MIA
Miami Intl.
IAD
Washington Dulles Intl.
$68 Roundtrip, found 5 days ago
$68
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Nov 24 from Miami Intl. to Washington Dulles Intl., returning Sun, Dec 7, priced at $68 found 5 days ago
Spirit Airlines
Thu, Nov 13 - Mon, Nov 17
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$87 Roundtrip, found 2 days ago
$87
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Nov 13 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Nov 17, priced at $87 found 2 days ago
Delta
Wed, Dec 3 - Tue, Dec 16
MIA
Miami Intl.
DCA
Ronald Reagan Washington National
$127 Roundtrip, found 5 days ago
$127
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Dec 3 from Miami Intl. to Ronald Reagan Washington National, returning Tue, Dec 16, priced at $127 found 5 days ago
JetBlue Airways
Thu, Nov 27 - Mon, Dec 1
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$132 Roundtrip, found 2 days ago
$132
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Nov 27 from Orlando Intl. to Ronald Reagan Washington National, returning Mon, Dec 1, priced at $132 found 2 days ago
United
Wed, Apr 1 - Tue, Apr 7
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Select United flight, departing Wed, Apr 1 from Logan Intl. to Washington Dulles Intl., returning Tue, Apr 7, priced at $167 found 4 days ago