Winchester Vacation Packages 2026 from $417

Winchester flight + hotel vacation packages

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

DoubleTree by Hilton Baltimore North - Pikesville

Save 100% on your flight

$417

per person

Sep 30 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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 and free WiFi in public areas. Free self parking, a snack bar/deli, and a hair salon are also offered.

Phoenix Park Hotel

Northwest

Save 100% on your flight

$563

per person

Sep 30 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Sheraton Baltimore North Hotel

Save 100% on your flight

$418

per person

Sep 30 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like a free area shuttle.

Furnished Apartments

Ashton Heights

Save 100% on your flight

$745

per person

Sep 9 - Sep 14

found 18 hours ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

This apartment features laundry facilities.

Hotel Burg

Leesburg's Old and Historic District

Save 100% on your flight

$1,102

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

This smoke-free hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and a terrace are also offered.

Stay near popular Winchester attractions

Museum of the Shenandoah Valley

8.8/10 (129 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.

See properties

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 $417. 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.