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Winchester flight + hotel packages

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Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was CA $1,019, price is now CA $725 per person
CA $725
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this business-friendly hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Union Station Shopping Center and Capital One Arena are located nearby.
Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland

5 out of 5
Save 100% on your flight
Price was CA $3,188, price is now CA $1,899 per person
CA $1,899
per person
Nov 1 - Nov 5
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this luxury B&B in Ridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Saint Jerome Beach and First District Community Park are located nearby.
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was CA $1,402, price is now CA $1,027 per person
CA $1,027
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this 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 Capital One Arena are located nearby.
Eaton DC

Eaton DC

4.5 out of 5
Downtown Washington D.C.
Price was CA $973, price is now CA $732 per person
CA $732
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, a full-service spa, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Capital One Arena and White House are located nearby.
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Price was CA $1,342, price is now CA $1,047 per person
CA $1,047
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this 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.

Top Winchester hotels deals

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
The price is CA $97 per night
CA $97
CA $107 total
Sep 27 - Sep 28
includes taxes & fees
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Apple Blossom Mall and R-C Track are located nearby.
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
Free cancellation
Reserve now, pay when you stay
The price is CA $184 per night
CA $184
CA $209 total
Oct 4 - Oct 5
includes taxes & fees
Book a stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Court House Civil War Museum and Bright Box Theater are located nearby.
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
The price is CA $154 per night
CA $154
CA $172 total
Sep 27 - Sep 28
includes taxes & fees
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 Apple Blossom Mall and R-C Track are located nearby.
Quality Inn Winchester

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
Free cancellation
The price is CA $119 per night
CA $119
CA $132 total
Oct 25 - Oct 26
includes taxes & fees
Stay at this 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 Rutherford Crossing and Northside Station Shopping Center are located nearby.
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
The price is CA $144 per night
CA $144
CA $160 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. 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.
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Free cancellation
Reserve now, pay when you stay
The price is CA $138 per night
CA $138
CA $153 total
Oct 4 - Oct 5
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Rutherford Crossing and Northside Station Shopping Center are located nearby.
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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

A brick pathway leading to a central lawn area, surrounded by trimmed hedges and trees.
Photo by Tina McClelland
Open Photo by Tina McClelland

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

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 $725. 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.

Photos of local treasures

Browse Winchester vacation photos for more inspiration

A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.
A historic downtown area with a prominent clock tower and a green-roofed building.
A historic building with a green dome and classical architecture.
A rocky coastline with waves crashing against the shore, a forested cliff, and a clear sky.
A serene garden with a clear stream, lush greenery, and flowering plants.