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 $54 and $27 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
TPABaltimoreOctober 26 to November 2$102
BOSChantillyOctober 11 to October 24$118
MCOWashingtonOctober 25 to October 25$122
DFWBaltimoreNovember 5 to November 12$128
MCOChantillyOctober 19 to October 24$128
MIAChantillyOctober 18 to October 30$138
MIAWashingtonOctober 18 to October 25$138
ATLChantillyNovember 9 to November 10$158
LAXBaltimoreNovember 1 to November 8$164
TPAWashingtonNovember 2 to November 15$176
DENChantillyOctober 18 to October 25$198
DFWChantillyOctober 30 to November 9$238
SFOChantillyNovember 1 to November 1$346
FCOBaltimoreDecember 2 to December 10$509
FCOWashingtonOctober 12 to October 18$534
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
BOSChantillyOctober 2 to October 22$138
ATLBaltimoreSeptember 30 to October 4$151
BOSWashingtonOctober 1 to October 5$178
BOSBaltimoreOctober 2 to October 5$200
MCOWashingtonOctober 1 to October 5$228
SFOWashingtonSeptember 30 to October 1$238
DFWWashingtonOctober 1 to October 12$308
LAXChantillySeptember 30 to October 4$320
TPAChantillySeptember 30 to October 9$409
DENWashingtonOctober 1 to October 6$428
DENChantillySeptember 30 to October 8$448
SFOBaltimoreOctober 2 to October 6$496
LAXWashingtonSeptember 30 to October 4$568
FCOChantillySeptember 30 to October 4$586
FCOBaltimoreSeptember 30 to October 4$710
*Prices include taxes and fees

Winchester Flight Information

Traveling to Winchester
Lowest Price $54
Number of Airlines Serving
Airlines Serving Spirit Airlines, United, JetBlue Airways
Number of Daily Flights
Airlines with Direct Flights

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, 22601
The price is $70 per night from Oct 2 to Oct 3
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the convenient parking in ...
4/5 Very Good! (972 reviews)
Traveling
"I stop here when I am traveling North or South."

Reviewed on Aug 24, 2022

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA, 22602
The price is $72 per night from Oct 2 to Oct 3
Stay at this business-friendly motel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms ...
3.8/5 Good! (1,005 reviews)
"Everything about the property was great, just not excellent. My only even kind of complaint was that the shower curtain smelled a bit musty."

Reviewed on Sep 25, 2022

Twi-Lite Inn

Twi-Lite Inn

2 out of 5
53 West 14th Street, Front Royal, VA, 22630
The price is $79 per night from Sep 29 to Sep 30
Stay at this motel in Front Royal. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the convenient parking in ...
3.9/5 Very Good! (369 reviews)
"This is a quaint, older motel. It was a little like stepping back in time with modern conveniences. The room was clean, the bed was comfy and the TV was a modern flat screen.. Don't overlook this motel!"

Reviewed on Sep 6, 2022

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You could be seeing lower prices

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Royal Inn Motel

Royal Inn Motel

2.5 out of 5
533 S. Royal Avenue, Front Royal, VA, 22630
Stay at this business-friendly motel in Front Royal. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. ...
3.2/5 (121 reviews)
Excellent for a roadside motel
"It’s a roadside motel. Extremely cheap. For the price- it was excellent. Beds comfortable enough. Not enough towels. No toiletries besides soap. NO COFFEE MAKER. That was strange. BUT the room was big and had fridge and microwave. Overall very happy."

Reviewed on Dec 23, 2020

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, 22601
The price is $70 per night from Oct 2 to Oct 3
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the convenient parking in ...
4/5 Very Good! (972 reviews)
Traveling
"I stop here when I am traveling North or South."

Reviewed on Aug 24, 2022

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA, 22602
The price is $72 per night from Oct 2 to Oct 3
Stay at this business-friendly motel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms ...
3.8/5 Good! (1,005 reviews)
"Everything about the property was great, just not excellent. My only even kind of complaint was that the shower curtain smelled a bit musty."

Reviewed on Sep 25, 2022

Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA, 22645
The price is $130 per night from Sep 29 to Sep 30
Stay at this 3.5-star hotel in Middletown. Enjoy free WiFi, free parking, and a terrace. Our guests praise the WiFi and the bar in our reviews. Popular attractions ...
4.6/5 Exceptional! (266 reviews)
"It was a pleasant stay in a unique inn."

Reviewed on Jul 24, 2022

You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Hotel Strasburg

Hotel Strasburg

3 out of 5
213 S. Holliday Street, Strasburg, VA, 22657-2213
Stay at this 3-star historic hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the restaurant and the helpful staff in ...
3.9/5 Good! (728 reviews)
awful
"The place was closed and looks like it has been for quite sometime. The outside was run down and litter all over. We drove 5 hours to get there and even had a confirmation number from hotel. Com. Very disappointed!!!!!!"

Reviewed on Oct 5, 2020

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, 22602
The price is $103 per night from Oct 2 to Oct 3
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 ...
4.4/5 Excellent! (1,003 reviews)

Families like: Indoor pools, extra beds/cribs, free breakfast for the whole family, laundry

Travelers say...
"We love the convenience and the friendliness of the staff. We travel with a pet and our room is near the exit on the first floor near our vehicle making everything very convenient. The location is great with easy on/off I-81."

Reviewed on Sep 24, 2022

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, 22657
The price is $123 per night from Oct 5 to Oct 6
Stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
4.4/5 Wonderful! (871 reviews)

Families like: Indoor pools, free breakfast for the whole family, laundry

Travelers say...
"Staff was courteous and knowledgeable. Facility was very clean and comfortable."

Reviewed on Sep 15, 2022

Quality Inn
Great for families

Quality Inn

2.5 out of 5
1601 Martinsburg Pike, Winchester, VA, 22603
The price is $93 per night from Oct 2 to Oct 3
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 ...
4.3/5 Excellent! (699 reviews)

Families like: Outdoor pool, extra beds/cribs, free breakfast for the whole family, laundry

Travelers say...
"All ok"

Reviewed on Sep 18, 2022

You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Hampton Inn Front Royal
Great for families

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd, Front Royal, VA, 22630
The price is $118 per night from Oct 5 to Oct 6
Stay at this business-friendly hotel in Front Royal. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
4.4/5 Excellent! (999 reviews)

Families like: Indoor pools, free breakfast for the whole family, laundry

Travelers say...
"Wide variety of breakfast, elevators kinda took a while if ur on the higher floor"

Reviewed on Sep 16, 2022

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.

Best Winchester Flight and Hotel Packages

Winchester flight + hotel packages - economy flights

Viceroy Washington DC
Hyatt Place National Harbor
Hotel Zena, a Viceroy Urban Retreat
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See all available trips from Atlanta to Winchester
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Need a Car For After Your Flight?

Frequently asked questions

Can I catch a flight to Winchester at the moment?
The Covid-19 Travel Advisor is the place to go for the most up-to-date info about travel restrictions and quarantine requirements for passengers flying in to Winchester.
Which airlines fly to Winchester?
Whether you’re seeking first-rate service or tasty in-flight meals on your flight to Winchester, you’re bound to find what you’re looking for. There are 20 carriers that advertise flights to this city, including:

  • United Airlines
  • American Airlines
  • Delta Air Lines

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.
Where to stay in Winchester
Few things are as satisfying as sliding into bed after a big day of sightseeing. With an impressive 45 accommodations in Winchester, you can have your pick of the comfiest of them.The The George Washington Hotel, A Wyndham Grand Hotel and the City Charmer Near Historic Oldtown Winchester are some of Travelocity’s top accommodation options in the Winchester area.
Places to visit in Winchester
Whether you’re looking to splurge, or simply grab the necessities, you’ll be treated to some fine retail therapy at Apple Blossom Mall. Want some more options? If you’re looking to stay on top of your health while on vacation, why not get physical at Jim Barnett Park? This popular recreation area will get you out of the gym and into the open air. But there’s more. Shenandoah Valley Discovery Museum has plenty of hands-on activities for active discovery. Your youngsters will be entertained for ages!
How to get through airport security fast when traveling to Winchester
Make your flight to Winchester a little easier by following these useful security tips:

  • Have your travel ID and boarding pass within easy reach. They’ll be the first things you’ll be instructed to produce by airport security staff.
  • You’ll need to put your tunes on pause for a little while. Earphones and headphones must be removed and put in a tray for X-raying. The same goes for items such as belts and heavy jackets.
  • Laptops need to be taken out of their protective carry bags and placed in a tray before going through the X-ray machine.
  • Toothpaste, lip balm and other toiletry items in gel, liquid or cream form need to be stored in containers smaller than 3.4 ounces (100 milliliters). They must also fit in a 1-quart (1-liter) clear zip-lock bag.
  • Think about the type of footwear you want to travel in. Slippers are awesome because they’re a cinch to step out of when you’re at the security checkpoint. Try wearing a pair on your next flight!
  • Some places have strict quarantine laws. Consider where you’re going to and whether or not you’re permitted to travel with fruit and meats.

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.