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 a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
2.11 km from Winchester Historic District
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
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. ...
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. ...
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 ...
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 ...
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 ...
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 ...
Hillbrook Inn

Hillbrook Inn

4 out of 5
4490 Summit Point Road Charles Town WV
21.81 km from Winchester Historic District
Book a stay at this business-friendly B&B in Charles Town. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the property condition in our ...
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 ...
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 ...
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 ...
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park

2 out of 5
111 South St Front Royal VA
30.44 km from Winchester Historic District
Stay at this hotel in Front Royal. Enjoy free breakfast, free WiFi, and free parking. 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 ...
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 ...
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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
Wed, Aug 12 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$76 Roundtrip, found 22 hours ago
$76
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 25, priced at $76 found 22 hours ago
Delta
Tue, Oct 13 - Tue, Oct 20
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$141 Roundtrip, found 14 hours ago
$141
Roundtrip
found 14 hours ago
Select Delta flight, departing Tue, Oct 13 from Logan Intl. to Ronald Reagan Washington National, returning Tue, Oct 20, priced at $141 found 14 hours ago
Southwest Airlines
Tue, Aug 11 - Wed, Aug 12
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$143 Roundtrip, found 11 hours ago
$143
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Tue, Aug 11 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Aug 12, priced at $143 found 11 hours ago
United
Tue, Sep 29 - Tue, Oct 6
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$143 Roundtrip, found 18 hours ago
$143
Roundtrip
found 18 hours ago
Select United flight, departing Tue, Sep 29 from Logan Intl. to Washington Dulles Intl., returning Tue, Oct 6, priced at $143 found 18 hours ago
American Airlines
Wed, Aug 12 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$177 Roundtrip, found 21 hours ago
$177
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Tue, Sep 1, priced at $177 found 21 hours ago