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.
Hotel Arboretum
Northeast
Save 100% on your flight
Price was $460, price is now $297 per person
$297
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling on business? Take advantage of the 4 onsite conference rooms. A gym is on site, and self parking and a 24-hour front desk are also offered.
SIXTY DC
Downtown Washington D.C.
Save 100% on your flight
Price was $1,104, price is now $628 per person
$628
per person
Nov 3 - Nov 8
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking is offered and the front desk is staffed around-the-clock.
Kimpton George Hotel by IHG
Northwest
Save 100% on your flight
Price was $536, price is now $334 per person
$334
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
A 24-hour gym, valet parking, and concierge services are featured at this hotel. Traveling on business? Take advantage of the business center and WiFi in public areas. Express check-out, dry cleaning, and luggage storage are also on offer.
Historic Inns of Annapolis
Historic District
Save 100% on your flight
Price was $661, price is now $426 per person
$426
per person
Nov 6 - Nov 9
found 22 hours 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.
Hampton Inn Towson Downtown
Save 100% on your flight
Price was $745, price is now $483 per person
$483
per person
Oct 30 - Nov 4
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Top Old Town Winchester hotels deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
$127 nightly
The price is $144 total per night
$144 total
Oct 9 - Oct 10
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.
Pool
Spa
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
$108 nightly
The price is $118 total per night
$118 total
Oct 5 - Oct 6
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
Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$83 nightly
The price is $94 total per night
$94 total
Oct 31 - Nov 1
Total with taxes and fees
This hotel features an outdoor 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 buffet breakfast and free self parking.
Pool
Breakfast included
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$78 nightly
The price is $84 total per night
$84 total
Oct 31 - Nov 1
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
$96 nightly
The price is $104 total per night
$104 total
Oct 12 - Oct 13
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
Travelodge by Wyndham Winchester
160 Front Royal Pike, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $78 total per night
$78 total
Oct 1 - Oct 2
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
Don't see what you're looking for?
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
Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
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.
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.
Frequently asked questions
Photos of local treasures
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