Old Town Winchester Vacation Packages 2026 from $686

Old Town Winchester flight + hotel vacation packages

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

Hotel AKA Washington Circle

Downtown Washington D.C.

Save 100% on your flight

$686

per person

Jun 4 - Jun 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Washington (DCA)

This aparthotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking, limo/town car service, and dry cleaning are also offered.

Global Luxury Suites at Capitol Hill

Northeast

Save 100% on your flight

$942

per person

Jun 4 - Jun 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Washington (DCA)

This aparthotel features a seasonal outdoor pool and a rooftop terrace. WiFi in public areas is free. Self parking is offered and multilingual staff can provide around-the-clock assistance.

Arlo Washington DC

Northwest

Save 100% on your flight

$700

per person

Jun 4 - Jun 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Washington (DCA)

The hotel's 24-hour gym, seasonal outdoor pool, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free WiFi. Self parking, a coffee shop, and dry cleaning are also offered.

Placemakr Buzzard Point

Southwest

Save 100% on your flight

$1,152

per person

May 17 - May 22

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Washington (DCA)

A 24-hour gym, self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A communal living room and luggage storage are also provided.

Top Old Town Winchester hotels deals

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$138 total

Mar 29 - Mar 30

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool 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. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.

Pool

Spa

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike Winchester VA

Free Cancellation

$98 nightly

$106 total

Mar 29 - Mar 30

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

La Quinta Inn & Suites by Wyndham Winchester

1055 Millwood Pike, Route 50 East Winchester VA

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$117 total

Mar 23 - Mar 24

Total with taxes and fees

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

Sleep Inn & Suites Winchester near University

140 Costello Dr Winchester VA

Free Cancellation

$80 nightly

$87 total

Apr 12 - Apr 13

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.

Breakfast included

Parking included

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

Free Cancellation

Reserve now, pay when you stay

$86 nightly

$94 total

Mar 24 - Mar 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

Hampton Inn Winchester-University/Mall Area

640 East Jubal Early Drive Winchester VA

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$115 total

Mar 29 - Mar 30

Total with taxes and fees

This hotel features an outdoor 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 buffet breakfast and free self parking.

Pool

Breakfast 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.

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.

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 top-notch restaurants or charming coffeehouses in this walkable area.

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 $686. 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!