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 ...
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 ...
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
3.05 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 ...
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

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 ...
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 ...
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 ...
The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

3 out of 5
100 Hollywood Dr Charles Town WV
30.2 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 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 ...
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 ...
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

3 out of 5
250 Front Royal Pike Winchester VA
3.06 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 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 ...
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 ...
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 ...
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. ...
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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
Tue, Apr 28 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$66 Roundtrip, found 5 hours ago
$66
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Apr 28 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, May 13, priced at $66 found 5 hours ago
Breeze Airways
Fri, Apr 17 - Sun, Apr 19
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$98 Roundtrip, found 18 hours ago
$98
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Fri, Apr 17 from Orlando Intl. to Washington Dulles Intl., returning Sun, Apr 19, priced at $98 found 18 hours ago
Spirit Airlines
Tue, Apr 14 - Wed, Apr 15
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$114 Roundtrip, found 18 hours ago
$114
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Tue, Apr 14 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Apr 15, priced at $114 found 18 hours ago
Delta
Tue, Jun 9 - Wed, Jun 10
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$117 Roundtrip, found 18 hours ago
$117
Roundtrip
found 18 hours ago
Select Delta flight, departing Tue, Jun 9 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Jun 10, priced at $117 found 18 hours ago
JetBlue Airways
Thu, Apr 30 - Sun, May 3
FLL
Fort Lauderdale - Hollywood Intl.
DCA
Ronald Reagan Washington National
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Apr 30 from Fort Lauderdale - Hollywood Intl. to Ronald Reagan Washington National, returning Sun, May 3, priced at $157 found 2 days ago