Cheap Flights to Winchester from $30

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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 $60 and $30 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
ATLChantillyFebruary 2 to February 2$63
ATLBaltimoreFebruary 2 to February 2$63
FLLBaltimoreDecember 25 to January 1$65
DFWBaltimoreJanuary 25 to February 6$68
CLTBaltimoreJanuary 15 to January 18$68
DFWChantillyJanuary 18 to January 18$95
FLLWashingtonJanuary 17 to January 18$117
ATLWashingtonJanuary 20 to January 24$139
BOSBaltimoreJanuary 23 to January 30$139
BOSChantillyJanuary 28 to February 1$142
LAXWashingtonJanuary 31 to January 31$187
LAXBaltimoreJanuary 7 to January 30$188
DFWWashingtonJanuary 28 to January 31$192
LAXChantillyFebruary 26 to March 7$192
SFOBaltimoreDecember 14 to January 8$222
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
FLLBaltimoreNovember 29 to December 13$216
ATLChantillyNovember 29 to December 7$221
ATLBaltimoreNovember 30 to December 6$227
BOSChantillyNovember 29 to December 3$232
CLTChantillyNovember 30 to December 8$338
BOSWashingtonNovember 30 to December 3$345
MCOWashingtonNovember 29 to December 1$391
LAXWashingtonNovember 29 to December 2$397
SFOWashingtonNovember 29 to December 4$433
FLLWashingtonNovember 29 to December 13$459
DFWBaltimoreNovember 29 to December 2$470
ATLWashingtonNovember 30 to December 1$538
SFOChantillyNovember 29 to December 14$539
BOSBaltimoreNovember 30 to December 1$630
SFOBaltimoreNovember 30 to December 3$681
*Prices include taxes and fees

Winchester Flight Information

Traveling to
Winchester
Lowest Price
$60
Number of Airlines Serving
Airlines Serving
Frontier Airlines
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
$68 nightly
The price is $77 total per night from Nov 30 to Dec 1
$77 total
Nov 30 - Dec 1
Total with taxes and fees
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 clean rooms in our reviews. ...
8/10 Very Good! (1,005 reviews)
Great room at a great price. Front desk staff went above and beyond to make it a great stay.

Reviewed on Nov 19, 2025

Opens in a new windowMotel 6 Winchester, VA
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
$68 nightly
The price is $74 total per night from Dec 1 to Dec 2
$74 total
Dec 1 - Dec 2
Total with taxes and fees
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 clean rooms in our reviews. ...
8.4/10 Very Good! (1,093 reviews)
Clean and comfortable.

Reviewed on Nov 23, 2025

Opens in a new windowTravelodge by Wyndham Winchester
Twi-Lite Inn

Twi-Lite Inn

2 out of 5
53 West 14th Street Front Royal VA
$65 nightly
The price is $72 total per night from Nov 30 to Dec 1
$72 total
Nov 30 - Dec 1
Total with taxes and fees
Stay at this motel in Front Royal. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
8/10 Very Good! (537 reviews)
Clean, very cute room! I love how old school it all was. The heat lamp in the bathroom took me back to my childhood. Very happy with my stay.

Reviewed on Nov 19, 2025

Opens in a new windowTwi-Lite Inn
Save an average of 15% on thousands of hotels when you're signed in
Royal Inn Motel

Royal Inn Motel

2.5 out of 5
533 S. Royal Avenue Front Royal VA
Stay at this motel in Front Royal. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Blue Ridge Arts Council and Gallery and Front ...
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

Opens in a new windowRoyal 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
$68 nightly
The price is $77 total per night from Nov 30 to Dec 1
$77 total
Nov 30 - Dec 1
Total with taxes and fees
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 clean rooms in our reviews. ...
8/10 Very Good! (1,005 reviews)
Great room at a great price. Front desk staff went above and beyond to make it a great stay.

Reviewed on Nov 19, 2025

Opens in a new windowMotel 6 Winchester, VA
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
$68 nightly
The price is $74 total per night from Dec 1 to Dec 2
$74 total
Dec 1 - Dec 2
Total with taxes and fees
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 clean rooms in our reviews. ...
8.4/10 Very Good! (1,093 reviews)
Clean and comfortable.

Reviewed on Nov 23, 2025

Opens in a new windowTravelodge by Wyndham Winchester
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St Middletown VA
$131 nightly
The price is $144 total per night from Dec 1 to Dec 2
$144 total
Dec 1 - Dec 2
Total with taxes and fees
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Wayside ...
9.2/10 Wonderful! (404 reviews)
heater worked well, room was neat and clean.

Reviewed on Nov 17, 2025

Opens in a new windowWayside Inn
Save an average of 15% on thousands of hotels when you're signed in
Hotel Strasburg

Hotel Strasburg

3 out of 5
213 S. Holliday Street Strasburg VA
Book a stay at this historic hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Strasburg Museum and Hupp's Hill Civil ...
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

Opens in a new windowHotel Strasburg
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

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd Winchester VA
$97 nightly
The price is $105 total per night from Dec 17 to Dec 18
$105 total
Dec 17 - Dec 18
Total with taxes and 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 ...
8.6/10 Excellent! (1,005 reviews)
As long as I don’t experience anything negative then my stay was great

Reviewed on Nov 20, 2025

Opens in a new windowCountry Inn & Suites by Radisson, Winchester, VA
Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley

2.5 out of 5
33760 Old Valley Pike Strasburg VA
$101 nightly
The price is $113 total per night from Dec 7 to Dec 8
$113 total
Dec 7 - Dec 8
Total with taxes and fees
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (1,000 reviews)
Everything was wonderful, especially the mattress which appeared new and was very firm but soft on top.

Reviewed on Nov 2, 2025

Opens in a new windowFairfield Inn & Suites Strasburg Shenandoah Valley
Quality Inn Winchester

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
$76 nightly
The price is $82 total per night from Dec 7 to Dec 8
$82 total
Dec 7 - Dec 8
Total with taxes and 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 ...
9.2/10 Wonderful! (1,003 reviews)
Great room, even better staff! I enjoyed the breakfast as well. Can’t wait to come back!!

Reviewed on Nov 19, 2025

Opens in a new windowQuality Inn Winchester
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Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd Front Royal VA
$99 nightly
The price is $110 total per night from Dec 7 to Dec 8
$110 total
Dec 7 - Dec 8
Total with taxes and fees
Book a 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 ...
9/10 Wonderful! (1,002 reviews)
Very clean room , the staff was very friendly and a good breakfast.

Reviewed on Nov 15, 2025

Opens in a new windowHampton 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.

Best Winchester Flight and Hotel Packages

Winchester flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Eurostars Saint Gregory Dupont Circle Georgetown
InterContinental Washington D.C. - The Wharf by IHG
Home2 Suites By Hilton Ashburn, Va
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Need a Car For After Your Flight?

Lowest prices found within the past 2 days. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

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

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!

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*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.