Search Deals on
Old Town Winchester Vacation Packages

Old Town Winchester Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Baltimore Inner Harbor

Comfort Inn & Suites Baltimore Inner Harbor

3 out of 5
Downtown Baltimore
Price was $919, price is now $407 per person
$407
per person
Oct 22 - Oct 27
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Stay at this hotel in Baltimore. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Baltimore Inner Harbor Marina and Oriole Park at Camden Yards are located nearby.
Omni Shoreham Hotel Washington DC

Omni Shoreham Hotel Washington DC

4 out of 5
Northwest
Price was $930, price is now $448 per person
$448
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Book a stay at this business-friendly hotel in Washington. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions White House and Capital One Arena are located nearby.
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,287, price is now $714 per person
$714
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Capital One Arena are located nearby.
Hotel Hive

Hotel Hive

3.5 out of 5
Northwest
Save 100% on your flight
Price was $704, price is now $441 per person
$441
per person
Oct 30 - Nov 5
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Stay at this hotel in Washington. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and National Mall are located nearby.
Glover Park Hotel Georgetown

Glover Park Hotel Georgetown

4 out of 5
Northwest
Save 100% on your flight
Price was $927, price is now $588 per person
$588
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Stay at this aparthotel in Washington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions White House and Arlington National Cemetery are located nearby.
The Georgetown Inn

The Georgetown Inn

4.5 out of 5
Northwest
Save 100% on your flight
Price was $1,669, price is now $1,068 per person
$1,068
per person
Oct 26 - Nov 2
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Arlington National Cemetery are located nearby.
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $812, price is now $533 per person
$533
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Book a stay at this business-friendly hotel in Washington. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions White House and Capital One Arena are located nearby.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $704, price is now $462 per person
$462
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Book a stay at this business-friendly hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Union Station Shopping Center and Capital One Arena are located nearby.

3-4 Night Vacations in Old Town Winchester

Price found within the past 48 hours. Click for updated prices.
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $446, price is now $272 per person
$272
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Save 100% on your flight
Price was $750, price is now $462 per person
$462
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Club Quarters Hotel White House, Washington DC

Club Quarters Hotel White House, Washington DC

3 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $637, price is now $394 per person
$394
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was $1,787, price is now $1,116 per person
$1,116
per person
Oct 16 - Oct 19
just found
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)

5-7 Night Vacations in Old Town Winchester

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Baltimore Inner Harbor

Comfort Inn & Suites Baltimore Inner Harbor

3 out of 5
Downtown Baltimore
Price was $919, price is now $407 per person
$407
per person
Oct 22 - Oct 27
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Omni Shoreham Hotel Washington DC

Omni Shoreham Hotel Washington DC

4 out of 5
Northwest
Price was $1,182, price is now $586 per person
$586
per person
Oct 25 - Oct 30
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,287, price is now $714 per person
$714
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Hotel Hive

Hotel Hive

3.5 out of 5
Northwest
Save 100% on your flight
Price was $704, price is now $441 per person
$441
per person
Oct 30 - Nov 5
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)

Cheap Hotel Deals in Old Town Winchester

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
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 ...
Opens in a new windowThe 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
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowTravelodge by Wyndham Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
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. ...
Opens in a new windowTRU By Hilton Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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
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 ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham Winchester
Quality Inn Winchester

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Opens in a new windowQuality Inn Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
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 ...
Opens in a new windowMicrotel Inn & Suites by Wyndham Winchester
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
Book a stay at this spa hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
Opens in a new windowComfort Inn & Suites Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
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 ...
Opens in a new windowRamada by Wyndham Strasburg/Shenandoah Valley
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

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, Oct 27 - Mon, Nov 9
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$56 Roundtrip, found 11 hours ago
$56
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Tue, Oct 27 from Orlando Intl. to Washington Dulles Intl., returning Mon, Nov 9, priced at $56 found 11 hours ago
Frontier Airlines
Tue, Oct 13 - Mon, Oct 19
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, found 12 hours ago
$56
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, Oct 13 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Oct 19, priced at $56 found 12 hours ago
Frontier Airlines
Thu, Nov 19 - Tue, Dec 1
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$60 Roundtrip, found 12 hours ago
$60
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Thu, Nov 19 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Tue, Dec 1, priced at $60 found 12 hours ago
Frontier Airlines
Wed, Oct 7 - Thu, Oct 15
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, just found
$60
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Oct 7 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Oct 15, priced at $60 just found