Old Town Winchester Vacation Packages 2025/2026 from $342

Old Town Winchester flight + hotel vacation packages

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

InterContinental Washington D.C. - The Wharf by IHG

Southwest

Save 100% on your flight

per person

Sep 5 - Sep 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Washington (DCA)

This smoke-free hotel features a full-service spa, a marina, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free area shuttle.

Kellogg Conference Hotel at Gallaudet University

Northeast

Save 100% on your flight

per person

Oct 11 - Oct 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Washington (WAS)

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.

SIXTY DC

Downtown Washington D.C.

Save 100% on your flight

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Washington (DCA)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking is offered and the front desk is staffed around-the-clock.

Hotel Burg

Save 100% on your flight

per person

Aug 29 - Sep 1

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to Washington (WAS)

This hotel features a restaurant and 3 bars/lounges. Enjoy the 24-hour gym and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

The St. Gregory Hotel

Downtown Washington D.C.

Save 100% on your flight

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Washington (DCA)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking. A terrace, limo/town car service, and a lobby fireplace are also on offer.

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

$127 nightly

$144 total

Jul 27 - Jul 28

Total includes 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

La Quinta Inn & Suites by Wyndham Winchester

1055 Millwood Pike, Route 50 East, Winchester, VA

Free Cancellation

Reserve now, pay when you stay

$104 nightly

$113 total

Jul 27 - Jul 28

Total includes 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

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza, Winchester, VA

Free Cancellation

Reserve now, pay when you stay

$82 nightly

$90 total

Aug 17 - Aug 18

Total includes 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

Travelodge by Wyndham Winchester

160 Front Royal Pike, Winchester, VA

Free Cancellation

Reserve now, pay when you stay

$69 nightly

$75 total

Jul 27 - Jul 28

Total includes 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

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike, Winchester, VA

Free Cancellation

$92 nightly

$100 total

Aug 3 - Aug 4

Total includes 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

Comfort Inn & Suites

195 Kernstown Commons Blvd, Winchester, VA

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$105 total

Aug 3 - Aug 4

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free self-serve breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Pet friendly

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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

Handley Regional Library

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.

Shenandoah Valley Discovery Museum

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

Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.

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 $342. 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!