Cheap Flights to Winchester from $25

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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 $50 and $25 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

Mon, Dec 29 - Wed, Jan 7
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$58 Roundtrip, found 14 hours ago
$58
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Mon, Dec 29 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Jan 7, priced at $58 found 14 hours ago
Thu, Nov 13 - Sat, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$63 Roundtrip, found 4 hours ago
$63
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Thu, Nov 13 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Nov 15, priced at $63 found 4 hours ago
OriginDestinationTravel DatesFlights From*
ATLChantillyDecember 31 to January 4$50
MCOChantillyDecember 21 to December 30$51
MCOBaltimoreDecember 16 to January 1$55
ATLBaltimoreDecember 29 to January 7$58
MIAChantillyJanuary 30 to February 2$64
MIABaltimoreJanuary 8 to January 11$64
DENWashingtonJanuary 31 to February 7$72
DFWChantillyJanuary 14 to January 18$90
MCOWashingtonJanuary 7 to January 12$107
BOSChantillyJanuary 17 to January 20$117
MIAWashingtonJanuary 9 to January 12$127
ATLWashingtonDecember 6 to December 13$137
DENBaltimoreNovember 10 to November 13$142
DENChantillyNovember 15 to November 19$142
BOSBaltimoreNovember 15 to November 20$142
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCOChantillyOctober 31 to November 3$132
BOSChantillyNovember 1 to November 2$149
MIAChantillyOctober 31 to November 3$158
MCOWashingtonOctober 31 to November 4$206
MIABaltimoreOctober 31 to November 2$227
ATLWashingtonNovember 1 to November 7$263
BOSWashingtonNovember 1 to November 5$280
LAXBaltimoreNovember 1 to November 4$283
DENBaltimoreNovember 1 to November 2$315
DALChantillyNovember 2 to November 8$316
DENChantillyOctober 31 to November 2$344
DENWashingtonOctober 31 to December 2$357
BOSBaltimoreOctober 31 to November 2$373
LAXWashingtonNovember 1 to November 4$459
LAXChantillyOctober 31 to November 3$580
*Prices include taxes and fees

Winchester Flight Information

Traveling to
Winchester
Lowest Price
$50
Number of Airlines Serving
Airlines Serving
Frontier Airlines, Spirit 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 Oct 29 to Oct 30
$77 total
Oct 29 - Oct 30
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! (1,001 reviews)
Good area to walk your dogs if they travel with you

Reviewed on Oct 24, 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
$69 nightly
The price is $75 total per night from Nov 2 to Nov 3
$75 total
Nov 2 - Nov 3
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 breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,107 reviews)
Clean room and eat on and off to I81

Reviewed on Oct 25, 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
$64 nightly
The price is $71 total per night from Nov 27 to Nov 28
$71 total
Nov 27 - Nov 28
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! (528 reviews)
yes and yes

Reviewed on Oct 19, 2025

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 ...
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
$68 nightly
The price is $77 total per night from Oct 29 to Oct 30
$77 total
Oct 29 - Oct 30
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! (1,001 reviews)
Good area to walk your dogs if they travel with you

Reviewed on Oct 24, 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
$69 nightly
The price is $75 total per night from Nov 2 to Nov 3
$75 total
Nov 2 - Nov 3
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 breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,107 reviews)
Clean room and eat on and off to I81

Reviewed on Oct 25, 2025

Opens in a new windowTravelodge by Wyndham Winchester
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
$130 nightly
The price is $143 total per night from Nov 2 to Nov 3
$143 total
Nov 2 - Nov 3
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! (399 reviews)
Historic inn.

Reviewed on Oct 20, 2025

Opens in a new windowWayside Inn
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Hotel Strasburg

Hotel Strasburg

3 out of 5
213 S. Holliday Street, Strasburg, VA
Stay at this 3-star 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

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
$91 nightly
The price is $99 total per night from Nov 9 to Nov 10
$99 total
Nov 9 - Nov 10
Total with taxes and fees
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 ...
8.6/10 Excellent! (1,003 reviews)
Not many options.

Reviewed on Oct 21, 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
$113 nightly
The price is $126 total per night from Nov 9 to Nov 10
$126 total
Nov 9 - Nov 10
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! (1,003 reviews)
Always a pleasure staying here

Reviewed on Oct 21, 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
$79 nightly
The price is $86 total per night from Nov 23 to Nov 24
$86 total
Nov 23 - Nov 24
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! (1,001 reviews)
Will definitely stay again when In the area

Reviewed on Oct 20, 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
$114 nightly
The price is $127 total per night from Nov 9 to Nov 10
$127 total
Nov 9 - Nov 10
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 ...
8.8/10 Excellent! (1,022 reviews)
All was great and the front desk staff were very helpful with recommendations for dining and skyline drive. The breakfast was good. My only complaint was that the coffee cups leaked a bit. Overall great stay.

Reviewed on Oct 22, 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.
Holiday Inn Washington-Dulles International Airport by IHG

Holiday Inn Washington-Dulles International Airport by IHG

3.5 out of 5
Save 100% on your flight
Price was $265, price is now $177 per person
$177
per person
Dec 6 - Dec 9
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
Embassy Suites by Hilton Washington D.C. – Convention Center

Embassy Suites by Hilton Washington D.C. – Convention Center

3.5 out of 5
Save 100% on your flight
Price was $582, price is now $376 per person
$376
per person
Dec 6 - Dec 9
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
Fairfax Marriott at Fair Oaks

Fairfax Marriott at Fair Oaks

4 out of 5
Save 100% on your flight
Price was $292, price is now $205 per person
$205
per person
Dec 6 - Dec 9
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
Don't see what you're looking for?
See all available trips from Atlanta to Winchester
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Winchester flight + hotel packages - premium economy flights

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Price was $650, price is now $543 per person
$543
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
Placemakr Buzzard Point

Placemakr Buzzard Point

2.5 out of 5
Price was $740, price is now $631 per person
$631
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

3.5 out of 5
Price was $670, price is now $581 per person
$581
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
Don't see what you're looking for?
See all available trips from Atlanta to Winchester
View all trips

Winchester flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Baltimore BWI Airport by IHG

Holiday Inn Baltimore BWI Airport by IHG

3 out of 5
Price was $1,159, price is now $1,087 per person
$1,087
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Baltimore (BWI)
Hotel Revival Baltimore

Hotel Revival Baltimore

4 out of 5
Price was $3,059, price is now $2,632 per person
$2,632
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Baltimore (BWI)
Merriweather Lakehouse, Autograph Collection

Merriweather Lakehouse, Autograph Collection

4 out of 5
Price was $1,302, price is now $1,218 per person
$1,218
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Baltimore (BWI)
Don't see what you're looking for?
See all available trips from Tampa to Winchester
View all trips

Need a Car For After Your Flight?

Midsize

  • 5 people
  • Unlimited mileage
Arlington, Virginia, USA

$39

$104 total
found 1 day ago
Midsize undefined

Standard

  • 5 people
  • Unlimited mileage
Arlington, Virginia, USA

$39

$104 total
found 1 day ago
Standard undefined

Fullsize

  • 5 people
  • Unlimited mileage
Arlington, Virginia, USA

$41

$108 total
found 1 day ago
Fullsize undefined

Special

  • 4 people
  • Unlimited mileage
Arlington, Virginia, USA

$44

$116 total
found 1 day ago
Special undefined

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.