Winchester Vacations 2025 from CA $466

Winchester flight + hotel packages

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

Hotel Arboretum

Northeast

per person

Aug 28 - Aug 31

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Washington (DCA)

Book a stay at this business-friendly hotel in Washington. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Union Station Shopping Center and Capital One Arena are located nearby.

Glover Park - Georgetown

Northwest

per person

Aug 28 - Aug 31

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Washington (DCA)

Stay at this aparthotel in Washington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions White House and Washington Monument are located nearby.

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.

per person

Aug 28 - Aug 31

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Washington (DCA)

Stay at this 5-star luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and National Museum of African American History and Culture are located nearby.

Lyle Washington D.C.

Northwest

per person

Aug 1 - Aug 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Washington (DCA)

Stay at this 4.5-star luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the bar in our reviews. Popular attractions White House and Capital One Arena are located nearby.

Hilton Alexandria Old Town

Old Town Alexandria

per person

Aug 1 - Aug 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Washington (DCA)

Book a stay at this business-friendly hotel in Alexandria. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MGM National Harbor Casino and Arlington National Cemetery are located nearby.

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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Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Apple Blossom Mall and Abram's Delight are located nearby.

Pool

Breakfast included

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike, Winchester, VA

Free cancellation

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Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Apple Blossom Mall and Abram's Delight are located nearby.

Pool

Parking included

Travelodge by Wyndham Winchester

160 Front Royal Pike, Winchester, VA

Free cancellation

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Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Apple Blossom Mall and Abram's Delight are located nearby.

Pet-friendly

Parking included

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza, Winchester, VA

Free cancellation

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Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rutherford Crossing and Northside Station Shopping Center are located nearby.

Pool

Breakfast included

Comfort Inn & Suites

195 Kernstown Commons Blvd, Winchester, VA

Free cancellation

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Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Appleland Sports Center and The Kernstown Battlefield are located nearby.

Breakfast included

Pet-friendly

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St, Winchester, VA

Free cancellation

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Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Old Court House Civil War Museum and Bright Box Theater are located nearby.

Spa

Free WiFi

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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(1 review)

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

Handley Regional Library

5/5(1 review)

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(1 review)

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

It's always good to know a thing or two about your destination before you head off on your escape. Circle Winchester on a map now and start packing your bags for your next great adventure!

To help you get your bearings, Winchester lies 65 miles (105 kilometers) west of the significant city of Washington.

Eager to mix with the locals? That shouldn't be an issue. 26,000 people call this part of Shenandoah Valley home.

Places to visit in Winchester

Some of the region's most creative intellects were nurtured in the classrooms of Shenandoah University. After spending a couple of hours here, you might have a lightbulb moment too! Want some more options? Shopaholics listen up — you'll be able to treat yourself to some impulse buying at Apple Blossom Mall. Ready to work that bank card and buy up a storm? And that's not all there is. Nothing compares to seeing top-notch art when your spirit needs lifting. As you marvel at the astounding works at Museum of the Shenandoah Valley, try to pinpoint the deeper meaning.

Where do you fly into for Winchester?

Put your seat in the upright position and get ready to experience Winchester! Once you hit the runway at Washington Dulles International Airport (IAD), the bustling main streets will be just 40 miles (64 kilometers) to the west of here.

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 CA $466. 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 105 kilometers 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), 64 kilometers east of the city center, is where many visitors begin their Winchester adventures. But it's possible that Hagerstown Regional Airport (HGR) (72 kilometers 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.