Old Town Winchester Vacation Packages 2026 from $406

Old Town Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Kellogg Conference Hotel at Gallaudet University

Northeast

$406

per person

Oct 8 - Oct 11

found 19 hours ago

Roundtrip flight included

Denver (DEN) 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.

Phoenix Park Hotel

Northwest

Save 100% on your flight

$731

per person

Oct 11 - Oct 15

found 17 hours ago

Roundtrip flight included

Denver (DEN) to Baltimore (BWI)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a 24-hour business center, and express check-out are also offered.

Crowne Plaza Crystal City-Washington, D.C. by IHG

Crystal City

Save 100% on your flight

$639

per person

Oct 11 - Oct 15

found 17 hours ago

Roundtrip flight included

Denver (DEN) 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, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and a terrace are also offered.

Elegant 2BR Apartment - Minutes to D.C.

Crystal City

Save 100% on your flight

$848

per person

Oct 11 - Oct 15

found 17 hours ago

Roundtrip flight included

Denver (DEN) to Baltimore (BWI)

A seasonal outdoor pool, self parking, and a virtual front desk are featured at this apartment. Staff at the 24-hour front desk can provide around-the-clock assistance.

The Watergate Hotel

Northwest

$714

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip flight included

Denver (DEN) to Baltimore (BWI)

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Make the most of the 24-hour gym and a rooftop terrace, and relax with drinks at one of the 3 bars/lounges.

Stay near popular Old Town Winchester attractions

Shenandoah Valley Discovery Museum

8.6/10 (78 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.

See properties

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 $406. 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!