Winchester Historic District Vacations from $191

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The Latest Winchester Historic District Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Price was $307, price is now $191 per person
$191
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,007 reviews)
Better than expected for the price. Very nice staff and clean. 1 or 2 questionable people outside during our 5 day stay, but nobody bothered us at all. I’d stay here again.

Reviewed on Nov 6, 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was $930, price is now $569 per person
$569
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,285 reviews)

citizenM Washington DC Capitol

citizenM Washington DC Capitol

4 out of 5
Southwest
Price was $554, price is now $352 per person
$352
per person
Jan 20 - Jan 25
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (3,400 reviews)
Staff

Reviewed on Nov 6, 2026

Harbor free indoor parking

Harbor free indoor parking

4 out of 5
Downtown Baltimore
Price was $476, price is now $304 per person
$304
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
No reviews

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was $721, price is now $461 per person
$461
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,007 reviews)

Winchester Historic District 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
$130 nightly
The price is $148 total per night from Nov 19 to Nov 20
$148 total
Nov 19 - Nov 20
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $77 total per night from Dec 1 to Dec 2
$77 total
Dec 1 - Dec 2
Total with taxes and fees
8.6/10 Excellent! (1,074 reviews)
"Staff was great. Beds were comfortable."

Reviewed on Nov 6, 2026

Travelodge by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $89 total per night from Nov 9 to Nov 10
$89 total
Nov 9 - Nov 10
Total with taxes and fees
Microtel Inn & Suites by Wyndham Winchester
See all 385 properties in Winchester Historic District
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Stay near popular Winchester Historic District attractions

Shenandoah Valley Discovery Museum

8.6/10 (78 reviews)
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.