Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Flights to Winchester

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How Much Does it Cost To Fly To Winchester?

The cheapest prices found with in the last 7 days for return flights were $41 and $21 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
MCOBaltimoreAug 18 - Aug 25$41
MCOSterlingSep 7 - Sep 18$52
ATLBaltimoreAug 18 - Aug 22$74
DENBaltimoreAug 30 - Sep 9$111
ATLSterlingAug 21 - Sep 1$117
MCOWashingtonAug 24 - Aug 26$117
BOSWashingtonSep 29 - Sep 29$128
BOSSterlingAug 24 - Sep 7$133
LAXBaltimoreAug 28 - Aug 30$136
TPASterlingAug 24 - Sep 12$159
DFWSterlingOct 19 - Oct 30$241
SFOWashingtonSep 8 - Sep 28$263
FCOSterlingSep 20 - Oct 5$451
FCOWashingtonSep 8 - Sep 21$475
FCOBaltimoreAug 19 - Aug 27$559
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCOBaltimoreAug 8 - Aug 10$137
ATLBaltimoreAug 6 - Aug 9$172
TPABaltimoreAug 8 - Aug 11$190
MIABaltimoreAug 8 - Aug 24$194
MCOSterlingAug 6 - Aug 17$197
MIASterlingAug 7 - Aug 23$229
DENWashingtonAug 6 - Aug 24$237
LAXBaltimoreAug 6 - Aug 24$246
BOSWashingtonAug 6 - Aug 15$294
DENBaltimoreAug 6 - Aug 9$295
LAXWashingtonAug 6 - Aug 9$295
LAXSterlingAug 6 - Aug 11$362
SFOWashingtonAug 7 - Aug 11$436
SFOSterlingAug 7 - Aug 28$444
FCOBaltimoreAug 6 - Aug 17$761
*Prices include taxes and fees

Flight Review

Find The Perfect Hotel For After Your Flight

Amazing Winchester Accommodation Deals

Motel 6 Winchester, VA

Motel 6 Winchester, VA

2 out of 5
2951 Valley Avenue, Winchester, VA
The price is $60 per night from Aug 8 to Aug 8
Located in the heart of Winchester, this motel is 0.8 mi (1.2 km) from The Kernstown Battlefield and within 3 mi (5 km) of Apple Blossom Mall and Abram's Delight. ...
3.5/5Good! (15 reviews)
"Surprisingly clean room with microwave and fridge. TV working. Also a small table with chairs. Nothing elegant but great for short stay. Very pleased!"

Reviewed on Nov 23, 2020

Motel 6 Winchester, VA
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2 out of 5
160 Front Royal Pike, Winchester, VA
The price is $57 per night from Aug 8 to Aug 8
Situated in Winchester, this motel is within a 15-minute walk of Valley Health and Shenandoah University. Apple Blossom Mall and Winchester-Frederick County ...
3.6/5Good! (28 reviews)
"Clean rooms,polite staff"

Reviewed on May 4, 2021

Travelodge by Wyndham Winchester
Twi-Lite Motel

Twi-Lite Motel

2 out of 5
53 West 14th Street, Front Royal, VA
The price is $74 per night from Aug 4 to Aug 4
Situated in Front Royal, this motel is within a 10-minute walk of Shenandoah River and Warren Memorial Hospital. Bing Crosby Stadium and Belle Boyd Cottage are ...
3/5 (2 reviews)
"Sad condition. Old and in need of a lot of work. I don’t know of anything good to say about it."

Reviewed on Oct 14, 2019

Twi-Lite Motel
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Royal Inn Motel

Royal Inn Motel

2.5 out of 5
533 S. Royal Avenue, Front Royal, VA
Situated in Front Royal, this motel is within a 15-minute walk of Blue Ridge Arts Council and Gallery, Front Royal Visitor's Center, and Belle Boyd Cottage. ...
4/5Very Good! (2 reviews)
Spending the night before a conference.
"We choose to spend the night instead of driving back for a morning conference. We wanted a basic place to sleep without amenities and that is what we got. The bed was reasonable but the heating system continued to cycle all night long very loudly. Other than that it was good for the price."

Reviewed on Dec 11, 2016

Royal Inn Motel
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.

Luxury Hotels in Winchester

Motel 6 Winchester, VA

Motel 6 Winchester, VA

2 out of 5
2951 Valley Avenue, Winchester, VA
The price is $60 per night from Aug 8 to Aug 8
Located in the heart of Winchester, this motel is 0.8 mi (1.2 km) from The Kernstown Battlefield and within 3 mi (5 km) of Apple Blossom Mall and Abram's Delight. ...
3.5/5Good! (15 reviews)
"Surprisingly clean room with microwave and fridge. TV working. Also a small table with chairs. Nothing elegant but great for short stay. Very pleased!"

Reviewed on Nov 23, 2020

Motel 6 Winchester, VA
The Ashby Inn & Restaurant

The Ashby Inn & Restaurant

3.5 out of 5
692 Federal St, Paris, VA
Situated in the historical district, this bed & breakfast is within a 15-minute walk of Paris Barns and Sky Meadows State Park. Shenandoah River and Burwell-Morgan ...
3/5 (1 review)
"Excellent food and portion size with great service for group dinner. Room disappointing. Stayed in New England room as could not do stairs to West Dominion. No view of countryside. Bathroom mirror too high for me (4ft, 9in) to use. Bed high but comfortable. Port wine nice touch. Not advised no TV ..."

Reviewed on May 23, 2018

The Ashby Inn & Restaurant
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2 out of 5
160 Front Royal Pike, Winchester, VA
The price is $57 per night from Aug 8 to Aug 8
Situated in Winchester, this motel is within a 15-minute walk of Valley Health and Shenandoah University. Apple Blossom Mall and Winchester-Frederick County ...
3.6/5Good! (28 reviews)
"Clean rooms,polite staff"

Reviewed on May 4, 2021

Travelodge by Wyndham Winchester
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Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
Situated in Middletown, this hotel is 1.4 mi (2.3 km) from Cedar Creek Battlefield Foundation and 2.1 mi (3.4 km) from Belle Grove Plantation. Valerie Hill Winery ...
4.5/5Wonderful! (4 reviews)
"A B&B full of history. Our host Tammy grew up in Middletown and was well versed on the Wayside Inn and the history of the area. It wasn't busy when we were there, so she spent nearly half an hour talking about this Inn that was established in 1797 and has been in continuous operation since. There ..."

Reviewed on Mar 11, 2019

Wayside Inn
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.

Family Friendly Hotels in Winchester

Country Inn & Suites by Radisson, Winchester, VA
Great for families

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
The price is $100 per night from Sep 1 to Sep 1
Situated in Winchester, this hotel is 2.2 mi (3.5 km) from The Kernstown Battlefield and within 6 mi (10 km) of Shenandoah University and Rock Harbor Golf Course. ...
4.6/5Exceptional! (33 reviews)
Families like: indoor pool, extra beds/cribs, free breakfast for the whole family, laundry
Travelers say...
"The suite was very clean and comfortable! Staff was incredibly friendly and helpful."

Reviewed on Oct 11, 2020

Country Inn & Suites by Radisson, Winchester, VA
Fairfield Inn & Suites Strasburg Shenandoah Valley
Great for families

Fairfield Inn & Suites Strasburg Shenandoah Valley

2.5 out of 5
33760 Old Valley Pike, Strasburg, VA
The price is $104 per night from Aug 4 to Aug 4
Situated in Strasburg, this hotel is within 2 mi (3 km) of Hupp's Hill Civil War Park, Strasburg Town Hall, and Strasburg Museum. Strasburg Theater and Cedar ...
4.8/5Exceptional! (11 reviews)
Families like: indoor pool, free breakfast for the whole family, laundry
Easter Stay
"We have always stayed at this particular Fairfield Inn when visiting our son in Strasburg. A couple of Christmases ago, our other son and his family stayed there, too and we had a great family reunion. The staff is always friendly and helpful, and the rooms are clean, the bathrooms well stocked with ..."

Reviewed on Apr 17, 2017

Fairfield Inn & Suites Strasburg Shenandoah Valley
Quality Inn
Great for families

Quality Inn

2.5 out of 5
1601 Martinsburg Pike, Winchester, VA
The price is $84 per night from Aug 5 to Aug 5
Situated in Winchester, this hotel is within 6 mi (10 km) of Stonewall Jackson's Headquarters, Handley Regional Library, and Mt Hebron Cemetery. Old Court House ...
4.6/5Exceptional! (17 reviews)
Families like: outdoor pool, extra beds/cribs, free breakfast for the whole family, laundry
Travelers say...
"Our room was very clean, updated & comfy. The location was a quick on/off art 81 with good quality restaurants nearby. Looking forward to staying again next vacation"

Reviewed on Jul 27, 2021

Quality Inn
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Hampton Inn Front Royal
Great for families

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd, Front Royal, VA
The price is $122 per night from Sep 1 to Sep 1
Situated in a national park, this hotel is 1 mi (1.6 km) from Shenandoah River and within 3 mi (5 km) of Warren Memorial Hospital and Blue Ridge Shadows Golf ...
4.3/5Excellent! (13 reviews)
Families like: pool, game room, free breakfast for the whole family, laundry
Travelers say...
"Very nice when you enter. Outside/parking lot we’ll kept."

Reviewed on Aug 11, 2019

Hampton Inn Front Royal
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.

Need a Car For After Your Flight?

Lowest prices found within the past 3 days. Prices and availability subject to change. Additional terms may apply.

Winchester Flight Information

Traveling to Winchester
Lowest Price $41
Number of Airlines Serving
Airlines Serving Spirit Airlines
Number of Daily Flights
Airlines with Direct Flights

FAQs about Winchester Flights

Can I catch a flight to Winchester at the moment?

Before committing to fly to Winchester, be sure to check out our Covid-19 Travel Advisor to see if there are any quarantine requirements or travel restrictions currently in place.

Which airlines fly to Winchester?

All geared up to explore the world? Hoping to kick off your adventure in Winchester? Just a few of the 20 air carriers that fly here are:

  • United Airlines
  • American Airlines
  • Southwest Airlines
If I am not able to travel due to COVID-19, can I change my booking to a later date?

For more info about changing your flight to Winchester, please visit our Customer Service Portal.

What airport is best to fly into Winchester?

Booking your airfare to Winchester is simple, as it has just one airport. You'll find Washington Dulles Intl. Airport (IAD) around 40 mi from all the action downtown.

Where to stay in Winchester

When Winchester starts whispering your name, it’s time to heed the call and reserve a fabulous place to stay with Travelocity. There are 46 accommodations in this wonderful destination for you to look into.

There's nothing more exciting than organizing your accommodations for your next vacation. But after hours of comparing amenities and prices, it can get a little tedious. So why not take our advice and choose one of our recommended properties, like The George Washington Hotel, A Wyndham Grand Hotel and the Wingate by Wyndham Winchester?

Places to visit in Winchester

You're sure to find the perfect gifts and souvenirs for your family and friends back home at Apple Blossom Mall. Make sure you buy yourself a few treats, too! Like some more ideas? Bring the family for an afternoon of fun at Jim Barnett Park, a recreation park. But that's not all there is. Let the youngsters move around and amuse themselves in the exhibits at Shenandoah Valley Discovery Museum. It doesn't get any more interactive and entertaining than that!

What airlines currently ensure COVID-19 measures are used and social distancing rules are being enforced?

These are some of the airlines to opt for if you're looking for a carrier that has strict social distancing policies and COVID-19 measures: United Airlines, American Airlines and Delta.

Plane Tickets To Winchester

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Winchester. Browse through our inventory to explore a wide range of cheap flights to Winchester to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Winchester as you anxiously await to exit the plane and explore what Winchester has to offer. Considering all the amazing local food and culture in Winchester, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Winchester to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Winchester without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Winchester with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Winchester today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.