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.
Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Save 100% on your flight
Price was $353, price is now $236 per person
$236
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was $1,586, price is now $946 per person
$946
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
This smoke-free hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and a terrace are also offered.
Residence Inn by Marriott Washington, DC National Mall

Residence Inn by Marriott Washington, DC National Mall

3 out of 5
Southwest
Save 100% on your flight
Price was $1,216, price is now $730 per person
$730
per person
Jul 27 - Jul 30
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $634, price is now $402 per person
$402
per person
Aug 20 - Aug 24
found 23 hours 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.
Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $555, price is now $359 per person
$359
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This apartment features an area shuttle, free self parking, and a free grocery shopping service. Luggage storage and laundry facilities are also provided.

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
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $138 total per night
$138 total
Jul 2 - Jul 3
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
$77 nightly
The price is $87 total per night
$87 total
Jul 20 - Jul 21
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.
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
$76 nightly
The price is $83 total per night
$83 total
Jul 5 - Jul 6
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
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
$92 nightly
The price is $100 total per night
$100 total
Jul 26 - Jul 27
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.
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
$69 nightly
The price is $75 total per night
$75 total
Jun 28 - Jun 29
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.
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $90 total per night
$90 total
Jul 12 - Jul 13
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like daily breakfast and free self parking.
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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

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

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

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.

Handley Regional Library

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 $236. 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
A red brick church with a blue door and a clock tower.
A brick building with a cafe on the ground floor and a church steeple in the background.
Old Town Winchester