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.
Kellogg Conference Hotel at Gallaudet University
Northeast
Price was $530, price is now $371 per person
$371
per person
Aug 4 - Aug 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
Residence Inn by Marriott Washington, DC National Mall
Southwest
Price was $1,242, price is now $853 per person
$853
per person
Aug 4 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Baltimore (BWI)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the a rooftop terrace and free buffet breakfast each morning.
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Save 100% on your flight
Price was $635, price is now $436 per person
$436
per person
Aug 4 - Aug 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
A restaurant and a bar/lounge are featured at this hotel. Families will appreciate the onsite laundry facilities and in-room childcare. WiFi in public areas is free.
Welcoming DC Area Apartments
Groveton
Save 100% on your flight
Price was $942, price is now $657 per person
$657
per person
Jul 21 - Jul 28
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
A 24-hour gym, self parking, and barbecue grills are featured at this apartment. WiFi in public areas is free. Business travelers can take advantage of the 24-hour business center.
Historic Inns of Annapolis
Historic District
Save 100% on your flight
Price was $541, price is now $383 per person
$383
per person
Aug 4 - Aug 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A terrace, limo/town car service, and a garden are also on offer.
Top Old Town Winchester hotels deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
$122 nightly
The price is $138 total per night
$138 total
Jun 14 - Jun 15
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
$84 nightly
The price is $95 total per night
$95 total
Jun 28 - Jun 29
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
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Free Cancellation
Reserve now, pay when you stay
$104 nightly
The price is $113 total per night
$113 total
Jun 30 - Jul 1
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
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
Jun 3 - Jun 4
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
$90 nightly
The price is $98 total per night
$98 total
Jun 21 - Jun 22
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
$105 nightly
The price is $114 total per night
$114 total
Jul 2 - Jul 3
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
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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
Bright Box Theater
Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.
Shenandoah Valley Discovery Museum
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.
Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.
Frequently asked questions
Photos of local treasures
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