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.
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
Save 100% on your flight
Price was $1,146, price is now $681 per person
$681
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. A terrace, a lobby fireplace, and a computer station are also on offer.
InterContinental Washington D.C. - The Wharf by IHG
Southwest
Save 100% on your flight
Price was $1,755, price is now $1,184 per person
$1,184
per person
May 4 - May 8
found 9 hours ago
Roundtrip flight included
Mesa (AZA) to Washington (DCA)
This smoke-free hotel features a full-service spa, a marina, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free area shuttle.
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Save 100% on your flight
Price was $1,833, price is now $1,276 per person
$1,276
per person
May 4 - May 8
found 9 hours ago
Roundtrip flight included
Mesa (AZA) to Washington (DCA)
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.
Conrad Washington, DC
Downtown Washington D.C.
Save 100% on your flight
Price was $1,752, price is now $1,227 per person
$1,227
per person
Apr 30 - May 5
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
The hotel's 24-hour gym, a rooftop terrace, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A restaurant, a 24-hour front desk, and a terrace are also provided.
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
Mar 5 - Mar 6
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
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $119 total per night
$119 total
Mar 1 - Mar 2
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
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Free Cancellation
$86 nightly
The price is $94 total per night
$94 total
Mar 6 - Mar 7
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
TownePlace Suites by Marriott Front Royal
5 Caroline Drive Front Royal VA
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $128 total per night
$128 total
Mar 15 - Mar 16
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. 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
Sleep Inn & Suites Winchester near University
140 Costello Dr Winchester VA
Free Cancellation
$80 nightly
The price is $87 total per night
$87 total
Mar 19 - Mar 20
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.
Breakfast included
Parking included
Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive Winchester VA
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $115 total per night
$115 total
Mar 8 - Mar 9
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
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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
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.
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.
Frequently asked questions
Photos of local treasures
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