Deals on vacations and trips to Old Town Winchester

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Old Town Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Kimpton Banneker Hotel by IHG

Kimpton Banneker Hotel by IHG

4.5 out of 5
Downtown Washington D.C.
Price was $530, price is now $359 per person
$359
per person
Aug 13 - Aug 16
found 2 days 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 laundry service, conference space, and valet parking. A communal living room, luggage storage, and concierge services are also on offer.
DoubleTree by Hilton Baltimore North - Pikesville

DoubleTree by Hilton Baltimore North - Pikesville

4 out of 5
Save 100% on your flight
Price was $1,013, price is now $652 per person
$652
per person
Jun 19 - Jun 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a snack bar/deli, and a hair salon are also offered.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was $1,133, price is now $777 per person
$777
per person
Jul 2 - Jul 5
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.
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was $576, price is now $397 per person
$397
per person
Aug 13 - Aug 16
found 2 days 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 express check-out, laundry service, and valet parking. A terrace, a lobby fireplace, and a computer station are also on offer.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
Price was $531, price is now $366 per person
$366
per person
Jul 8 - Jul 11
found 19 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.

Top Old Town Winchester hotels deals

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
$122 nightly
The price is $138 total per night
$138 total
Jun 4 - Jun 5
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

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $90 total per night
$90 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
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $115 total per night
$115 total
Jun 2 - Jun 3
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

Travelodge by Wyndham Winchester

2.5 out of 5
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
May 25 - May 26
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

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $98 total per night
$98 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

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
Free Cancellation
$104 nightly
The price is $113 total per night
$113 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
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Lowest 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.

Shenandoah Valley Discovery Museum

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.

Bright Box Theater

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.

Old Court House Civil War Museum

Frequently asked questions

How much are vacation packages to Old Town Winchester?
Your travel dreams can all come true in Old Town Winchester from just $359. Our vacation packages include flights and hotels, and they'll make your booking a piece of cake. The only thing you'll need to focus on is what amazing attraction you'll head to first.
Where can I get the best vacation package deals for Old Town Winchester?
No matter how you like to travel, Travelocity can help you get your hands on the perfect Old Town Winchester package deal. All you have to do is pick and choose between our 400 airlines and 1,000,000 properties across the globe.
Why should I book my Old Town Winchester vacation bundle with Travelocity?
Savings, support and a stress-free booking are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you have access to our team of customer support experts around-the-clock. With the Travelocity Price Match Guarantee, you know you'll always get the best deal available.
Can I save money on my Old Town Winchester car rental if I bundle it with a hotel or flight?
Booking an Old Town Winchester vacation package with Travelocity is a surefire way to save you money. You can pick a hotel, car and flight, or any combination of them, and score great discounts. It's also possible to throw in activities and experiences. After you've collected the keys to the rental car, head out of the neighborhood and see what this place has to offer. Roughly 65 mi from Old Town Winchester, White House is certainly worth a road trip.
What is there to do in Old Town Winchester?
While exploring Old Town Winchester, don't forget to check out Shenandoah Valley Discovery Museum and Old Court House Civil War Museum. You won't be bored here!

Photos of local treasures

Browse Old Town Winchester vacation photos for more inspiration

The Courthouse in Winchester, Virginia.
Old Town Winchester
Old Town Winchester
Old Town Winchester
Old Town Winchester