Cheap Flights to Winchester from $21

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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 $42 and $21 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

Tue, Sep 15 - Wed, Sep 30
FLL
Fort Lauderdale - Hollywood Intl.
IAD
Washington Dulles Intl.
$42 Roundtrip, found 5 days ago
$42
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Sep 15 from Fort Lauderdale - Hollywood Intl. to Washington Dulles Intl., returning Wed, Sep 30, priced at $42 found 5 days ago
OriginDestinationTravel DatesFlights From*
FLLChantillySeptember 15 to September 30$42
ATLChantillyOctober 20 to October 22$80
ATLBaltimoreOctober 22 to October 25$95
BOSBaltimoreOctober 20 to October 22$117
BOSWashingtonOctober 20 to October 24$117
DFWChantillySeptember 22 to September 26$130
ATLWashingtonNovember 2 to November 3$150
FLLWashingtonOctober 7 to October 14$153
CLTChantillySeptember 14 to September 17$165
LAXBaltimoreOctober 27 to November 3$178
LAXWashingtonOctober 22 to October 27$178
DFWBaltimoreOctober 8 to October 12$196
DFWWashingtonOctober 28 to October 29$198
SFOWashingtonOctober 26 to October 31$278
SFOChantillySeptember 16 to September 23$282
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
FLLChantillyAugust 22 to September 21$237
CLTChantillyAugust 22 to August 24$268
ATLWashingtonAugust 22 to August 24$278
FLLBaltimoreAugust 23 to September 2$295
FLLWashingtonAugust 22 to September 2$317
BOSChantillyAugust 22 to August 23$336
DFWChantillyAugust 23 to September 4$347
BOSBaltimoreAugust 21 to August 23$357
ATLBaltimoreAugust 22 to August 30$365
DFWWashingtonAugust 23 to August 30$365
LAXChantillyAugust 22 to August 28$391
LAXWashingtonAugust 21 to August 25$401
LAXBaltimoreAugust 22 to August 24$401
SFOBaltimoreAugust 23 to August 25$486
SFOChantillyAugust 23 to August 25$486
*Prices include taxes and fees

Winchester Flight Information

Traveling to
Winchester
Lowest Price
$42
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 $81 total per night from Sep 2 to Sep 3
$81 total
Sep 2 - Sep 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 helpful staff and the clean rooms in our reviews. ...
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 $76 total per night from Aug 20 to Aug 21
$76 total
Aug 20 - Aug 21
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. ...
8.6/10 Excellent! (1,074 reviews)
"Convenient parking. Decent for an overnight stay."

Reviewed on Aug 17, 2026

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
$82 nightly
The price is $91 total per night from Aug 20 to Aug 21
$91 total
Aug 20 - Aug 21
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! (573 reviews)
"Everything was great, this was our 3rd year in a row and we always stay there. Quaint and all on 1 floor. Pool is also lovely. Will go again next year. But if you want to book a room, do it as early as possible because it does fill up fast"

Reviewed on Aug 13, 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 Front Royal Entrance Shenandoah National Park ...
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 $81 total per night from Sep 2 to Sep 3
$81 total
Sep 2 - Sep 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 helpful staff and the clean rooms in our reviews. ...
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 $76 total per night from Aug 20 to Aug 21
$76 total
Aug 20 - Aug 21
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. ...
8.6/10 Excellent! (1,074 reviews)
"Convenient parking. Decent for an overnight stay."

Reviewed on Aug 17, 2026

Opens in a new windowTravelodge by Wyndham Winchester
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St Middletown VA
$144 nightly
The price is $159 total per night from Aug 23 to Aug 24
$159 total
Aug 23 - Aug 24
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! (446 reviews)
"Clean room at a reasonable price. Interesting old inn."

Reviewed on Aug 11, 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
$95 nightly
The price is $106 total per night from Sep 15 to Sep 16
$106 total
Sep 15 - Sep 16
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! (1,002 reviews)
"Clean, well managed. , good breakfast."

Reviewed on Aug 18, 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 Sep 1 to Sep 2
$126 total
Sep 1 - Sep 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. ...
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 Aug 25 to Aug 26
$94 total
Aug 25 - Aug 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 ...
9.4/10 Exceptional! (1,008 reviews)
"It was very clean and convenient to where we wanted to go"

Reviewed on Aug 19, 2026

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
$122 nightly
The price is $136 total per night from Aug 25 to Aug 26
$136 total
Aug 25 - Aug 26
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! (1,016 reviews)
"This property is located right off the highway. It's walking distance to fast food. They served a free continental breakfast every morning. The staff were friendly and welcoming. We had a large party with 4 rooms, the check in and out was quick and easy."

Reviewed on Aug 19, 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.
Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Save 100% on your flight
Price was $710, price is now $438 per person
$438
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
The Poppy Georgetown

The Poppy Georgetown

4 out of 5
Price was $1,584, price is now $829 per person
$829
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
The LINE Hotel DC

The LINE Hotel DC

4.5 out of 5
Save 100% on your flight
Price was $802, price is now $502 per person
$502
per person
Oct 10 - Oct 14
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
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Winchester flight + hotel packages - premium economy flights

Price found within the past 48 hours. Click for updated prices.
The River Inn

The River Inn

4 out of 5
Price was $797, price is now $610 per person
$610
per person
Oct 8 - Oct 11
found 3 hours ago
Roundtrip flight included
Tampa (TPA) to Baltimore (BWI)
Hotel Washington

Hotel Washington

5 out of 5
Price was $909, price is now $689 per person
$689
per person
Oct 8 - Oct 11
found 3 hours ago
Roundtrip flight included
Tampa (TPA) to Baltimore (BWI)
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Price was $880, price is now $682 per person
$682
per person
Oct 8 - Oct 11
found 3 hours ago
Roundtrip 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

Winchester flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Price was $745, price is now $666 per person
$666
per person
Sep 25 - Sep 27
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Riggs Washington DC

Riggs Washington DC

5 out of 5
Price was $1,044, price is now $889 per person
$889
per person
Sep 25 - Sep 27
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Price was $888, price is now $779 per person
$779
per person
Sep 25 - Sep 27
found 12 hours 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

Need a Car For After Your Flight?

Economy

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

$36

$115 total
found 5 days ago
Economy undefined

Compact SUV

  • 5 people
  • Unlimited mileage
Baltimore, Maryland, USA

$37

$114 total
found 5 days ago
Compact SUV undefined

Midsize SUV

  • 5 people
  • Unlimited mileage
Baltimore, Maryland, USA

$39

$118 total
found 5 days ago
Midsize SUV undefined

Fullsize Elite Pickup Regular Cab

  • 6 people
  • Unlimited mileage
Baltimore, Maryland, USA

$40

$119 total
found 5 days ago
Fullsize Elite Pickup Regular Cab undefined
Lowest prices found within the past 5 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.