Deals on vacations and trips to Old Town Winchester
Old Town Winchester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott Alexandria Old Town South at Carlyle
Eisenhower East
Save 100% on your flight
Price was $962, price is now $604 per person
$604
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Placemakr Buzzard Point
Southwest
Save 100% on your flight
Price was $1,693, price is now $1,105 per person
$1,105
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
A 24-hour gym, self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A communal living room and luggage storage are also provided.
Lyle Washington D.C.
Northwest
Save 100% on your flight
Price was $1,106, price is now $725 per person
$725
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and a garden are also offered.
The River Inn
Northwest
Save 100% on your flight
Price was $1,120, price is now $742 per person
$742
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
This aparthotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. A terrace, a lobby fireplace, and luggage storage are also on offer.
Akeem's guest house
Save 100% on your flight
Price was $1,296, price is now $863 per person
$863
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Top Old Town Winchester hotels deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $138 total per night
$138 total
May 25 - May 26
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this Georgian hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.
Pool
Spa
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Free Cancellation
Reserve now, pay when you stay
$77 nightly
The price is $87 total per night
$87 total
May 31 - Jun 1
Total with taxes and fees
The hotel doesn't skimp on freebies - guests receive free continental breakfast and free self parking. Traveling for business? Take advantage of the business center, express check-out, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $77 total per night
$77 total
May 24 - May 25
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. There's express check-out and multilingual staff can provide around-the-clock assistance.
Pet friendly
Parking included
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Free Cancellation
Reserve now, pay when you stay
$92 nightly
The price is $100 total per night
$100 total
May 24 - May 25
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Free Cancellation
$100 nightly
The price is $109 total per night
$109 total
May 24 - May 25
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Parking included
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $126 total per night
$126 total
May 20 - May 21
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
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See all available properties in Old Town Winchester
View all propertiesLowest 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.
Popular places to visit
Shenandoah Valley Discovery Museum
4.5/5(11 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.
Bright Box Theater
4.5/5(4 reviews)
Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.
Old Court House Civil War Museum
You can study the exhibits at Old Court House Civil War Museum, a museum with a story of its own, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants.
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