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

Tue, Sep 23 - Sat, Sep 27
IAH
George Bush Intercontinental
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 1 hour ago
$60
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Sep 23 from George Bush Intercontinental to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Sep 27, priced at $60 found 1 hour ago
OriginDestinationTravel DatesFlights From*
MIABaltimoreSeptember 12 to September 15$71
ATLChantillySeptember 30 to October 8$76
DFWBaltimoreOctober 25 to October 27$88
DFWChantillySeptember 20 to September 21$89
LAXBaltimoreNovember 11 to November 15$90
DENBaltimoreSeptember 5 to September 8$117
MCOWashingtonSeptember 20 to September 20$122
BOSBaltimoreSeptember 3 to September 6$138
DALWashingtonSeptember 16 to September 20$139
BOSWashingtonSeptember 3 to September 3$154
SFOBaltimoreNovember 13 to November 16$187
SFOChantillyOctober 26 to November 1$215
FCOChantillyNovember 20 to November 27$465
FCOWashingtonOctober 24 to October 28$560
FCOBaltimoreSeptember 3 to September 7$604
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
DFWChantillyAugust 23 to September 14$203
TPAChantillyAugust 23 to August 27$223
TPABaltimoreAugust 23 to August 25$234
MCOBaltimoreAugust 23 to August 24$243
DFWWashingtonAugust 22 to August 23$251
BOSChantillyAugust 22 to August 24$258
SFOBaltimoreAugust 22 to August 25$312
LAXWashingtonAugust 23 to August 26$318
TPAWashingtonAugust 24 to August 26$343
BOSWashingtonAugust 23 to August 27$402
BOSBaltimoreAugust 24 to August 27$429
ATLWashingtonAugust 23 to August 25$460
LAXChantillyAugust 22 to August 26$468
FCOChantillyAugust 24 to September 7$751
FCOBaltimoreAugust 24 to October 4$825
*Prices include taxes and fees

Winchester Flight Information

Traveling to
Winchester
Lowest Price
$60
Number of Airlines Serving
Airlines Serving
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
$67 nightly
The price is $76 total per night from Sep 12 to Sep 13
$76 total
Sep 12 - Sep 13
Total includes 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! (1,004 reviews)
"Friendly staff, spotless rooms, safe property and location. Great place for those traveling with pets."

Reviewed on Aug 19, 2025

Motel 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 Aug 24 to Aug 25
$75 total
Aug 24 - Aug 25
Total includes 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! (1,085 reviews)
"We had a comfortable bed and a handicap shower with many great features. The staff helped us to find a great Thai restaurant. Couldn’t ask for more."

Reviewed on Aug 15, 2025

Travelodge by Wyndham Winchester
Twi-Lite Inn

Twi-Lite Inn

2 out of 5
53 West 14th Street, Front Royal, VA
$75 nightly
The price is $83 total per night from Aug 21 to Aug 22
$83 total
Aug 21 - Aug 22
Total includes 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! (520 reviews)
Simple and Clean
"With this place, you get what you pay for. Its inexpensive, so no lavish frills. Its dated, but that adds to the charm. If you want a clean and comfortable bed, clean room and clean towels, plenty of hot water, a mini-fridge and a pool right outside your door, this is the place for you. I used it ..."

Reviewed on Aug 15, 2025

Twi-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
Royal 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
$67 nightly
The price is $76 total per night from Sep 12 to Sep 13
$76 total
Sep 12 - Sep 13
Total includes 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! (1,004 reviews)
"Friendly staff, spotless rooms, safe property and location. Great place for those traveling with pets."

Reviewed on Aug 19, 2025

Motel 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 Aug 24 to Aug 25
$75 total
Aug 24 - Aug 25
Total includes 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! (1,085 reviews)
"We had a comfortable bed and a handicap shower with many great features. The staff helped us to find a great Thai restaurant. Couldn’t ask for more."

Reviewed on Aug 15, 2025

Travelodge by Wyndham Winchester
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
$112 nightly
The price is $123 total per night from Aug 24 to Aug 25
$123 total
Aug 24 - Aug 25
Total includes 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! (392 reviews)
"We stayed last year on July 4th. ...really liked it...decided to make it an annual event. I like the small town atmosphere."

Reviewed on Jul 7, 2025

Wayside 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
Hotel 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 $104 total per night from Aug 24 to Aug 25
$104 total
Aug 24 - Aug 25
Total includes 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! (1,005 reviews)
"Hotel is clean and comfortable. Plenty of tables and seating outside, breakfast was standard free breakfast. Rooms were all clean and had anything you’d need after a long day of traveling."

Reviewed on Aug 16, 2025

Country 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 Sep 15 to Sep 16
$126 total
Sep 15 - Sep 16
Total includes 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! (1,002 reviews)
"Everything was fine; nothing outstanding but nothing bad either. Good place for an overnight stay while traveling"

Reviewed on Aug 3, 2025

Fairfield 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 $83 total per night from Sep 15 to Sep 16
$83 total
Sep 15 - Sep 16
Total includes 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 ...
9/10 Wonderful! (1,008 reviews)
"Good people.Excellent service."

Reviewed on Aug 16, 2025

Quality 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
$121 nightly
The price is $135 total per night from Aug 24 to Aug 25
$135 total
Aug 24 - Aug 25
Total includes 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! (1,003 reviews)
"Great stay, clean and comfortable beds and bathroom. Free breakfast was very busy, but the staff did great at keeping it stocked and fresh. Had fun splashing in the pool."

Reviewed on Aug 17, 2025

Hampton 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
Save 100% on your flight
Price was $450, price is now $271 per person
$271
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (WAS)
Landing Washington DC near Washington Navy Yard

Landing Washington DC near Washington Navy Yard

2 out of 5
Save 100% on your flight
Price was $700, price is now $499 per person
$499
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
Sheraton Pentagon City Hotel

Sheraton Pentagon City Hotel

3.5 out of 5
Price was $456, price is now $326 per person
$326
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (WAS)
Don't see what you're looking for?
See all available trips from Boston to Winchester
View all trips

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 $724, price is now $472 per person
$472
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Washington (WAS)
Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Price was $820, price is now $595 per person
$595
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Washington (WAS)
Hilton Garden Inn Washington DC/U.S. Capitol

Hilton Garden Inn Washington DC/U.S. Capitol

3 out of 5
Price was $775, price is now $599 per person
$599
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Washington (WAS)
Don't see what you're looking for?
See all available trips from Minneapolis to Winchester
View all trips

Need a Car For After Your Flight?

Midsize

  • 5 people
  • Unlimited mileage
Arlington, Virginia, USA

$23

$65 total
found 13 hours ago
Midsize undefined

Economy

  • 4 people
  • Unlimited mileage
Arlington, Virginia, USA

$23

$65 total
found 13 hours ago
Economy undefined

Compact

  • 5 people
  • Unlimited mileage
Arlington, Virginia, USA

$23

$65 total
found 13 hours ago
Compact undefined

Special

  • 4 people
  • Unlimited mileage
Arlington, Virginia, USA

$25

$70 total
found 13 hours ago
Special undefined
Lowest prices found within the past 13 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!

*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.