Deals on vacations and trips to Winchester

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Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
Price was $425, price is now $252 per person
$252
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
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.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was $967, price is now $520 per person
$520
per person
Nov 4 - Nov 10
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 and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,104, price is now $628 per person
$628
per person
Nov 3 - Nov 8
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
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.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
Price was $661, price is now $426 per person
$426
per person
Nov 6 - Nov 9
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A terrace, limo/town car service, and a garden are also on offer.
Cambria Hotel Washington D.C. Navy Yard Riverfront

Cambria Hotel Washington D.C. Navy Yard Riverfront

3 out of 5
Southwest
Save 100% on your flight
Price was $838, price is now $542 per person
$542
per person
Dec 14 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A grocery/convenience store, a communal living room, and express check-out are also on offer.

Top Winchester hotels deals

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $100 total per night
$100 total
Oct 5 - Oct 6
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
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $118 total per night
$118 total
Oct 5 - Oct 6
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
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $78 total per night
$78 total
Oct 1 - Oct 2
Total with 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
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $91 total per night
$91 total
Oct 26 - Oct 27
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
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $101 total per night
$101 total
Oct 1 - Oct 2
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
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
Free Cancellation
$91 nightly
The price is $99 total per night
$99 total
Oct 26 - Oct 27
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 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

Gardens at Glen Burnie House.

Museum of the Shenandoah Valley

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.

Museum of the Shenandoah Valley
Staircase at Handley Library

Handley Regional Library

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.

Handley Regional Library

Winchester Medical Center

Though Winchester Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here.

Winchester Medical Center

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 $252. 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

Photos of local treasures

Browse Winchester vacation photos for more inspiration

Winchester
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby

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