Winchester Vacation Packages 2025 from $238

Winchester flight + hotel vacation packages

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

Hotel Arboretum

Northeast

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Washington (DCA)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling on business? Take advantage of the 4 onsite conference rooms. A gym is on site, and self parking and a 24-hour front desk are also offered.

SIXTY DC

Downtown Washington D.C.

Save 100% on your flight

per person

Jul 8 - Jul 12

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.

Canopy by Hilton Baltimore Harbor Point

Fells Point

Save 100% on your flight

per person

Jul 6 - Jul 11

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Baltimore (BWI)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and laundry service. Self parking, a terrace, and a snack bar/deli are also offered.

DoubleTree Hotel Baltimore - BWI Airport

Save 100% on your flight

per person

Jul 6 - Jul 11

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 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the seasonal outdoor pool and perks like free self parking and a free area shuttle.

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.

Save 100% on your flight

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Washington (DCA)

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.

Top Winchester hotels deals

La Quinta Inn & Suites by Wyndham Winchester

1055 Millwood Pike, Route 50 East, Winchester, VA

Free Cancellation

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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

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike, Winchester, VA

Free Cancellation

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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

Travelodge by Wyndham Winchester

160 Front Royal Pike, Winchester, VA

Free Cancellation

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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

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza, Winchester, VA

Free Cancellation

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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

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St, Winchester, VA

Free Cancellation

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A full-service spa, 2 restaurants, and a 24-hour gym 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. A bar/lounge, a 24-hour front desk, and a convenience store are also provided.

Spa

Free WiFi

Sleep Inn & Suites

140 Costello Dr, Winchester, VA

Free Cancellation

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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 full 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

Museum of the Shenandoah Valley

5/5(19 reviews)

You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.

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.

Shenandoah University

4.5/5(69 reviews)

Enjoy the collegiate vibe when you visit Shenandoah University, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants.

Winchester Vacations

Tourists regularly plan Winchester vacations to see the "Apple Capital" of the eastern seaboard. With vast orchards surrounding the city, this part of Virginia retains the robust apple industry of its founding days. When you're booking Winchester packages, look for deals around the spring and summer holidays, as they're the best time to experience local events and catch the peak of apple season.

Major Attractions in Winchester

Old Town Winchester is the tourist center of the city, home to dozens of historical attractions, plus over a hundred hotels, restaurants, and locally owned stores. It's also a great place to look for Winchester hotels, and its proximity to the Winchester Regional Airport makes it convenient to find Winchester rental cars.

Many tourist buffs book flights and Winchester all-inclusive vacations just to see the dozens of notable Civil War sites. You can even sign up for a guided tour of historic Civil War locations -- most reliably during the spring, summer, and fall, although tours exist year-round. Notable sites include the headquarters of Stonewall Jackson when he led campaigns in the area, and even the headquarters of General George Washington during the Revolutionary War.

Festivals and Events in Winchester

By far the biggest annual event in Winchester is the world-famous Shenandoah Apple Blossom Festival. Typically held at the start of May, this festival has grown to encompass more than 30 events, including barn dances, band competitions, multiple parades, a carnival, and a circus, plus it features a celebrity Grand Marshal.

Beyond the Apple Blossom Festival, Old Town Winchester hosts events throughout the year. With scavenger hunts in August and Civil War re-enactments from June through September, these activities take advantage of Old Town's deep historic heritage and its ample opportunities for delicious dining!

Book your vacation on Travelocity today, and enjoy the Travelocity Price Guarantee. If you find a better price, we'll refund the difference!

Frequently asked questions

How much are vacation packages to Winchester?

Travelocity offers package deals to Winchester, including hotels and flights, starting from as low as $238. With all the money you save, you could purchase some cool tours or maybe even add on a couple of extra days to your exciting getaway.

How long should my Winchester vacation be?

Around 2 nights is what most tourists book for their Winchester trip. That’s a handy guide, but there’s plenty more to discover if you allow yourself a little more time.

Where can I get the best vacation package deals for Winchester?

Head straight to Travelocity. With access to 400 airline partners and a massive 1,000,000 properties across the globe, creating the ultimate Winchester package deal couldn’t be simpler.

Why should I purchase my Winchester vacation package with Travelocity?

Because we believe in crafting unforgettable vacation experiences. From hotels and flights to car rentals and activities, our packages make traveling a breeze. Our customer support team is on hand 24/7 to make sure you’re being well taken care of. We also have an amazing Price Match Guarantee, so you can secure your vacation knowing you’ve landed the best deal around. If you find a lower price, we’ll match it!

Will I save money on my Winchester car rental if I bundle it with hotels and flights?

Bundling your hotel, car and flight into a Winchester vacation package is an easy way to land the best deal. Plus, having your own rental car gives you absolute freedom to get to all those famous sights you can’t wait to explore. Sitting 65 mi away from Winchester, White House is one attraction that should be on your to-do list. Put together a driving playlist and make a day trip of it.

Which airport is best for Winchester?

Washington Dulles Intl. Airport (IAD), 40 mi east of the city center, is where many visitors begin their Winchester adventures. But it’s possible that Hagerstown Regional Airport (HGR) (45 mi away from central Winchester) could be the more convenient option for you.

What is there to do in Winchester?

While venturing off the beaten track is no doubt rewarding, you really shouldn’t miss the big-name attractions that make a destination famous. Shenandoah University and Shenandoah Valley Discovery Museum are just two of them in Winchester.

Where should I stay when visiting Winchester?

The Country Inn & Suites by Radisson, Winchester, VA is popular with many visitors. Book now before it’s too late.

Where to stay in Winchester: Best areas for travelers

Blue Ridge: You won't need to choose between a nature escape and a city trip here. With popular attractions like Blue Ridge Center for Environmental Stewardship and Aldie Mill Historic Park, this Winchester neighborhood has the best of worlds. Discover these sights from the Goodstone Inn & Restaurant or the Salamander Resort And Spa. The Middleburg Historic District Charm is also a comfortable base.
Stephens City: You've made an itinerary of all the top attractions in town. Now all you need is a cozy hotel to return to. For an enjoyable vacation, lock in a room at the Quality Inn Stephens City-Winchester South or the Holiday Inn Express Winchester South-Stephens City.