Cheap Flights to Winchester from $20

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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 $43 and $20 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

Sat, Oct 24 - Sat, Oct 31
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$43 Roundtrip, found 1 day ago
$43
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Oct 24 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sat, Oct 31, priced at $43 found 1 day ago
Thu, Oct 22 - Sat, Oct 24
FLL
Fort Lauderdale - Hollywood Intl.
IAD
Washington Dulles Intl.
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 22 from Fort Lauderdale - Hollywood Intl. to Washington Dulles Intl., returning Sat, Oct 24, priced at $58 found 1 day ago
OriginDestinationTravel DatesFlights From*
ATLChantillyOctober 28 to October 31$64
DFWChantillyNovember 16 to November 21$90
FLLBaltimoreDecember 5 to December 8$108
DFWBaltimoreOctober 27 to October 31$115
BOSWashingtonOctober 26 to November 5$117
BOSBaltimoreOctober 26 to October 27$117
CLTWashingtonOctober 27 to October 31$162
FLLWashingtonOctober 31 to November 7$197
LAXChantillyOctober 28 to November 1$213
LAXWashingtonDecember 2 to December 16$238
LAXBaltimoreDecember 3 to December 7$238
SFOWashingtonOctober 31 to November 7$251
SFOBaltimoreOctober 26 to November 2$276
FCOChantillyOctober 21 to November 7$542
FCOBaltimoreNovember 21 to November 27$607
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ATLBaltimoreOctober 3 to October 7$262
ATLChantillyOctober 3 to October 7$262
FLLBaltimoreOctober 3 to October 4$267
MCOWashingtonOctober 3 to October 5$322
FLLWashingtonOctober 3 to October 8$374
DFWChantillyOctober 3 to October 4$387
DFWBaltimoreOctober 3 to October 4$387
BOSBaltimoreOctober 3 to October 10$391
DENBaltimoreOctober 4 to October 16$400
DFWWashingtonOctober 3 to October 4$488
LAXChantillyOctober 4 to October 11$494
BOSWashingtonOctober 4 to October 8$509
LAXWashingtonOctober 3 to October 4$551
ATLWashingtonOctober 3 to October 7$695
BOSChantillyOctober 3 to October 10$1,027
*Prices include taxes and fees

Winchester Flight Information

Traveling to
Winchester
Lowest Price
$43
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
$72 nightly
The price is $82 total per night from Oct 5 to Oct 6
$82 total
Oct 5 - Oct 6
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. ...
8.2/10 Very Good! (1,000 reviews)
"They book a lot of working construction people, which is fine, until 6am when they start their trucks and idle for 30 min., when it's 55 degrees. Then they pound on our door like we work for them and trying to get us up for work. Avoid this place if you can. We just needed a place for the night and ..."

Reviewed on Sep 30, 2026

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
$71 nightly
The price is $78 total per night from Oct 5 to Oct 6
$78 total
Oct 5 - Oct 6
Total with taxes and 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 ...
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
$77 nightly
The price is $86 total per night from Nov 1 to Nov 2
$86 total
Nov 1 - Nov 2
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 ...
8.2/10 Very Good! (582 reviews)
"You will get what is listed not more not less"

Reviewed on Sep 28, 2026

Opens in a new windowTwi-Lite Inn
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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 ...
6.4/10 (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

Get rates
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
$72 nightly
The price is $82 total per night from Oct 5 to Oct 6
$82 total
Oct 5 - Oct 6
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. ...
8.2/10 Very Good! (1,000 reviews)
"They book a lot of working construction people, which is fine, until 6am when they start their trucks and idle for 30 min., when it's 55 degrees. Then they pound on our door like we work for them and trying to get us up for work. Avoid this place if you can. We just needed a place for the night and ..."

Reviewed on Sep 30, 2026

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
$71 nightly
The price is $78 total per night from Oct 5 to Oct 6
$78 total
Oct 5 - Oct 6
Total with taxes and 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 ...
Opens in a new windowTravelodge by Wyndham Winchester
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St Middletown VA
$94 nightly
The price is $104 total per night from Oct 19 to Oct 20
$104 total
Oct 19 - Oct 20
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 Cedar ...
9.2/10 Wonderful! (449 reviews)
"Charmingly beautiful hotel. Like staying in a Civil War museum. Comfortable mattress. Slightly creaky bed. Got to hear the haunted boots on the wooden floor footsteps! Cute coffee shop next door. Will gladly be back!"

Reviewed on Sep 27, 2026

Opens in a new windowWayside Inn
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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 ...
7.8/10 Good! (731 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

Get rates
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
$94 nightly
The price is $105 total per night from Oct 25 to Oct 26
$105 total
Oct 25 - Oct 26
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 ...
8.8/10 Excellent! (1,001 reviews)
"I always look forward to my stay here while traveling. Always a clean room and a friendly desk staff to greet you . Nice breakfast in the morning"

Reviewed on Oct 1, 2026

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

Fairfield Inn & Suites Strasburg Shenandoah Valley

3 out of 5
33760 Old Valley Pike Strasburg VA
$113 nightly
The price is $126 total per night from Nov 1 to Nov 2
$126 total
Nov 1 - Nov 2
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. ...
9/10 Wonderful! (1,000 reviews)
"Friendly"

Reviewed on Sep 29, 2026

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
$84 nightly
The price is $94 total per night from Oct 25 to Oct 26
$94 total
Oct 25 - Oct 26
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 ...
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
$118 nightly
The price is $132 total per night from Nov 1 to Nov 2
$132 total
Nov 1 - Nov 2
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 ...
9.2/10 Wonderful! (1,007 reviews)
"Really enjoyed our stay at the Hampton Inn, in Front Royal. My wife and I took a trip to do a hiking weekend in Shenandoah National Park. With the hotel being close to the park, as well as just outside a relatively large town, so we'd have stuff to do in the evenings, the location was great. The ..."

Reviewed on Sep 28, 2026

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.
The Royal Sonesta Washington DC Dupont Circle

The Royal Sonesta Washington DC Dupont Circle

4.5 out of 5
Save 100% on your flight
Price was $400, price is now $255 per person
$255
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Save 100% on your flight
Price was $799, price is now $477 per person
$477
per person
Nov 11 - Nov 15
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
The Mayflower Hotel, Autograph Collection

The Mayflower Hotel, Autograph Collection

4 out of 5
Save 100% on your flight
Price was $821, price is now $504 per person
$504
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Don't see what you're looking for?
See all available trips from Atlanta to Winchester
View all trips

Winchester flight + hotel packages - premium economy flights

Price found within the past 48 hours. Click for updated prices.
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Price was $918, price is now $764 per person
$764
per person
Nov 13 - Nov 16
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Baltimore (BWI)
Club Quarters Hotel White House, Washington DC

Club Quarters Hotel White House, Washington DC

3 out of 5
Price was $1,049, price is now $832 per person
$832
per person
Nov 13 - Nov 16
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Baltimore (BWI)
Arlo Washington DC

Arlo Washington DC

4 out of 5
Price was $947, price is now $799 per person
$799
per person
Nov 13 - Nov 16
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Baltimore (BWI)
Don't see what you're looking for?
See all available trips from Los Angeles to Winchester
View all trips

Winchester flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Baltimore Downtown by IHG

Hotel Indigo Baltimore Downtown by IHG

4 out of 5
Price was $1,869, price is now $1,704 per person
$1,704
per person
Nov 11 - Nov 17
found 12 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Baltimore (BWI)
The William Fell Baltimore, Tapestry Collection by Hilton

The William Fell Baltimore, Tapestry Collection by Hilton

3.5 out of 5
Price was $2,174, price is now $1,951 per person
$1,951
per person
Nov 11 - Nov 17
found 12 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Baltimore (BWI)
Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

4.5 out of 5
Price was $1,971, price is now $1,815 per person
$1,815
per person
Nov 11 - Nov 17
found 12 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Baltimore (BWI)
Don't see what you're looking for?
See all available trips from Seattle to Winchester
View all trips

Need a Car For After Your Flight?

Economy

  • 5 people
  • Unlimited mileage
Hanover, District of Columbia, USA

$22

$80 total
found 2 days ago
Economy undefined

Compact

  • 5 people
  • Unlimited mileage
Hanover, USA

$22

$80 total
found 2 days ago
Compact undefined

Special

  • 5 people
  • Unlimited mileage
HANOVER, USA

$27

$87 total
found 2 days ago
Special undefined

Standard

  • 5 people
  • Unlimited mileage
Baltimore, Maryland, USA

$29

$92 total
found 2 days ago
Standard undefined
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!

Explore More Ways to Travel with Travelocity

*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.