Cheap Flights to Winchester from $29

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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 $58 and $29 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
ATLChantillyJanuary 13 to January 18$58
ATLBaltimoreFebruary 11 to February 21$58
FLLBaltimoreFebruary 27 to March 2$58
DFWBaltimoreJanuary 17 to January 18$65
DFWChantillyJanuary 8 to January 8$80
CLTBaltimoreFebruary 19 to February 26$80
LAXBaltimoreJanuary 24 to January 28$99
BOSBaltimoreJanuary 27 to January 31$130
BOSChantillyJanuary 26 to January 29$130
ATLWashingtonFebruary 21 to February 24$131
FLLWashingtonJanuary 28 to January 28$132
SFOBaltimoreJanuary 10 to January 19$141
BOSWashingtonJanuary 7 to January 7$156
CLTWashingtonJanuary 9 to January 11$189
FCOBaltimoreJanuary 22 to February 6$620
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCOBaltimoreDecember 20 to December 29$95
FLLChantillyDecember 21 to December 31$149
MCOChantillyDecember 20 to December 29$173
ATLChantillyDecember 20 to December 25$175
CLTChantillyDecember 21 to January 5$197
CLTBaltimoreDecember 20 to December 21$206
BOSWashingtonDecember 21 to December 29$228
BOSChantillyDecember 21 to December 28$237
FLLBaltimoreDecember 20 to December 21$242
ATLBaltimoreDecember 21 to December 25$256
FLLWashingtonDecember 21 to December 22$262
BOSBaltimoreDecember 21 to December 28$426
LAXChantillyDecember 20 to January 4$499
SFOWashingtonDecember 19 to December 26$668
FCOBaltimoreDecember 19 to February 1$850
*Prices include taxes and fees

Winchester Flight Information

Traveling to
Winchester
Lowest Price
$58
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 Dec 14 to Dec 15
$77 total
Dec 14 - Dec 15
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)
Very clean and nice very quiet everything stocked like it should easy access plenty parking and plenty room for your pets outside

Reviewed on Dec 11, 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 Jan 11 to Jan 12
$74 total
Jan 11 - Jan 12, 2026
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! (1,080 reviews)
Room clean, heater works great parking

Reviewed on Dec 7, 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
$62 nightly
The price is $69 total per night from Dec 14 to Dec 15
$69 total
Dec 14 - Dec 15
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! (540 reviews)
Room was very clean. Easy, efficient check-in, quiet, very comfortable beds.

Reviewed on Nov 23, 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 Dec 14 to Dec 15
$77 total
Dec 14 - Dec 15
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)
Very clean and nice very quiet everything stocked like it should easy access plenty parking and plenty room for your pets outside

Reviewed on Dec 11, 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 Jan 11 to Jan 12
$74 total
Jan 11 - Jan 12, 2026
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! (1,080 reviews)
Room clean, heater works great parking

Reviewed on Dec 7, 2025

Opens in a new windowTravelodge by Wyndham Winchester
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St Middletown VA
$89 nightly
The price is $98 total per night from Dec 14 to Dec 15
$98 total
Dec 14 - Dec 15
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! (406 reviews)
Brittany and the rest of the staff at Wayside were wonderful. They made us feel welcome, talked to us about the history and quirks of the, and our room was very quaint. The Christmas decorations in the room were a nice touch.

Reviewed on Nov 23, 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
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

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
$84 nightly
The price is $91 total per night from Jan 11 to Jan 12
$91 total
Jan 11 - Jan 12, 2026
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! (1,006 reviews)
Room was large, very clean and very comfortable.

Reviewed on Dec 7, 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 Dec 18 to Dec 19
$126 total
Dec 18 - Dec 19
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 Jan 4 to Jan 5
$82 total
Jan 4 - Jan 5, 2026
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)
Everything was great, including breakfast

Reviewed on Dec 6, 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
$107 nightly
The price is $119 total per night from Dec 21 to Dec 22
$119 total
Dec 21 - Dec 22
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! (1,001 reviews)
Everything was great about this Hampton Inn. It's dog friendly so i didn't know what to expect. It was very clean, nicely decorated (not dated) and the staff was super nice. Highly recommend it.

Reviewed on Dec 4, 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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Price was $692, price is now $332 per person
$332
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Save 100% on your flight
Price was $850, price is now $474 per person
$474
per person
Jan 18 - Jan 24
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 $637, price is now $365 per person
$365
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
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Need a Car For After Your Flight?

Economy

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

$33

$66 total
found 23 hours ago
Economy undefined

Compact

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

$33

$66 total
found 23 hours ago
Compact undefined

Midsize

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

$38

$76 total
found 23 hours ago
Midsize undefined

Special

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

$41

$82 total
found 23 hours ago
Special undefined
Lowest prices found within the past 23 hours. 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.