Old Town Winchester Vacation Packages 2026 from $407

Old Town Winchester flight + hotel vacation packages

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

The Normandy Hotel

Northwest

Save 100% on your flight

$407

per person

Nov 14 - Nov 17

found 21 hours ago

Roundtrip flight included

Dallas (DFW) to Baltimore (BWI)

This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Traveling on business? Take advantage of the 24-hour business center and valet parking. A terrace, a lobby fireplace, and a library are also on offer.

Placemakr Dupont Circle

Northwest

Save 100% on your flight

$704

per person

Nov 7 - Nov 13

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Baltimore (BWI)

A 24-hour gym is featured at this aparthotel, along with free WiFi in public areas and a terrace. A lobby fireplace, a library, and express check-out are also on offer.

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.

$599

per person

Dec 10 - Dec 13

found 8 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Baltimore (BWI)

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.

Fairmont Washington, D.C., Georgetown

Northwest

Save 100% on your flight

$677

per person

Nov 14 - Nov 17

found 21 hours ago

Roundtrip flight included

Dallas (DFW) to Baltimore (BWI)

The hotel's indoor pool, gym, and 2 bars/lounges are among the featured amenities. Families will appreciate complimentary bicycles, kid-friendly dining, and in-room childcare. Enjoy a meal from the restaurant and perks like free WiFi.

The Royal Sonesta Washington DC Capitol Hill

Northwest

Save 100% on your flight

$917

per person

Nov 7 - Nov 13

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Baltimore (BWI)

This hotel 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. Luggage storage, concierge services, and wedding services are also on offer.

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 $407. 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!