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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.
![Hilton Washington DC Capitol Hill](https://images.trvl-media.com/lodging/1000000/20000/11300/11216/d7f50212_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Hilton Washington DC Capitol Hill
Northwest
per person
Aug 28 - Aug 31
found 2 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Washington (DCA)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a snack bar/deli, and dry cleaning are also offered.
![Glover Park - Georgetown](https://images.trvl-media.com/lodging/1000000/10000/10000/9927/b0f618f6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Glover Park - Georgetown
Northwest
per person
Aug 28 - Aug 31
found 2 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Washington (DCA)
This aparthotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a terrace, and a snack bar/deli are also offered.
![Hotel Washington](https://images.trvl-media.com/lodging/1000000/20000/12100/12067/7327d9c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Hotel Washington
Downtown Washington D.C.
per person
Aug 28 - Aug 31
found 2 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Washington (DCA)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this boutique hotel. Enjoy the a rooftop terrace and perks like free WiFi. There's a bar/lounge on site, and concierge services and wedding services are also provided.
![Embassy Suites by Hilton Washington D.C. – Convention Center](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273382/d4fe452d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Embassy Suites by Hilton Washington D.C. – Convention Center
Downtown Washington D.C.
per person
Aug 28 - Aug 31
found 2 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Washington (DCA)
This aparthotel features an indoor pool, a 24-hour gym, and a restaurant. Enjoy the free cooked-to-order breakfast each morning. Valet parking, a snack bar/deli, and WiFi in public areas are also offered.
![The Dupont Circle Hotel](https://images.trvl-media.com/lodging/1000000/30000/25400/25341/bb100dbc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
The Dupont Circle Hotel
Northwest
per person
Aug 28 - Aug 31
found 2 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Washington (DCA)
This aparthotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a terrace, and limo/town car service are also on offer.
Top Old Town Winchester hotels deals
![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/d6b37fa1_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
The price is $125 per night
$125
per night
Jun 23 - Jun 24
A full-service spa, 2 restaurants, and a 24-hour gym 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. A bar/lounge, a 24-hour front desk, and a convenience store are also provided.
Pool
Spa
![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/c42f26ae_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
The price is $107 per night
$107
per night
Jun 23 - Jun 24
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
![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/07d2b628_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
The price is $87 per night
$87
per night
Jul 1 - Jul 2
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
![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/w3000h1998x0y0-d5a6974e_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Travelodge by Wyndham Winchester
160 Front Royal Pike, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
The price is $65 per night
$65
per night
Jun 30 - Jul 1
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Pool
Breakfast included
![Comfort Inn & Suites](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/0601aeca_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Comfort Inn & Suites
195 Kernstown Commons Blvd, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
The price is $94 per night
$94
per night
Jun 30 - Jul 1
This hotel doesn't skimp on freebies - guests receive free self-serve breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
![Spark by Hilton Winchester](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/f7bcf176_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Spark by Hilton Winchester
150 Wingate Dr, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
The price is $75 per night
$75
per night
Jul 22 - Jul 23
A gym, free self parking, and laundry facilities are featured at this hotel. Traveling for business? Take advantage of the business center, express check-out, and conference space. A safe deposit box is provided and the front desk is staffed around-the-clock.
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
5/5(2 reviews)
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.
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.
Photos of local treasures
Browse Old Town Winchester vacation photos for more inspiration
![Old Town Winchester](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)