Winchester Vacation Packages 2026 from $270

Winchester flight + hotel vacation packages

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

Kellogg Conference Hotel at Gallaudet University

Northeast

Save 100% on your flight

$270

per person

Sep 17 - Sep 20

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. 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.

Phoenix Park Hotel

Northwest

Save 100% on your flight

$335

per person

Sep 3 - Sep 7

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.

Eurostars Saint Gregory Dupont Circle Georgetown

Downtown Washington D.C.

Save 100% on your flight

$557

per person

Oct 10 - Oct 14

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. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. A terrace, a lobby fireplace, and a computer station are also on offer.

Crowne Plaza Crystal City-Washington, D.C. by IHG

Crystal City

Save 100% on your flight

$613

per person

Oct 7 - Oct 11

found 22 hours 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, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and a terrace are also offered.

Sheraton Baltimore North Hotel

Save 100% on your flight

$332

per person

Sep 27 - Oct 2

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.

Top Winchester hotels deals

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike Winchester VA

Free Cancellation

$86 nightly

$95 total

Aug 9 - Aug 10

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

TRU By Hilton Winchester

118 Mercedes Court Winchester VA

Free Cancellation

Reserve now, pay when you stay

$82 nightly

$91 total

Jul 30 - Jul 31

Total with taxes and fees

This hotel features an indoor 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 continental breakfast and free self parking.

Pool

Breakfast included

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

Free Cancellation

Reserve now, pay when you stay

$65 nightly

$73 total

Aug 2 - Aug 3

Total with taxes and fees

The hotel doesn't skimp on freebies - guests receive free continental breakfast and free self parking. Traveling for business? Take advantage of the business center, express check-out, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Pet friendly

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

Jul 30 - Jul 31

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this Georgian hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$102 total

Jul 26 - Jul 27

Total with taxes and fees

This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA

Free Cancellation

$98 nightly

$109 total

Aug 16 - Aug 17

Total with 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.

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 $270. 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.