Cheap Flights to Winchester from $44
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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 $44 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply
FLL
Fort Lauderdale - Hollywood Intl.
IAD
Washington Dulles Intl.
$90 Roundtrip, found 6 days ago
$90
Roundtrip
found 6 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Baltimore | September 16 to September 16 | $58 |
| ATL | Chantilly | September 12 to September 15 | $84 |
| CLT | Baltimore | July 15 to July 29 | $93 |
| BOS | Baltimore | July 25 to July 28 | $117 |
| BOS | Chantilly | August 22 to August 25 | $120 |
| DFW | Chantilly | August 25 to August 29 | $148 |
| CLT | Washington | September 30 to October 7 | $181 |
| FLL | Washington | August 18 to August 18 | $192 |
| CLT | Chantilly | August 12 to August 17 | $195 |
| DFW | Washington | September 2 to September 9 | $210 |
| LAX | Chantilly | September 9 to September 16 | $227 |
| LAX | Baltimore | August 4 to August 11 | $240 |
| SFO | Baltimore | July 15 to July 25 | $248 |
| SFO | Washington | September 1 to September 12 | $256 |
| FCO | Baltimore | September 24 to October 7 | $678 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| CLT | Baltimore | June 27 to August 10 | $173 |
| ATL | Baltimore | June 26 to June 27 | $251 |
| ATL | Chantilly | June 27 to June 28 | $262 |
| FLL | Washington | June 27 to July 6 | $289 |
| ATL | Washington | June 28 to July 2 | $313 |
| CLT | Chantilly | June 26 to June 28 | $317 |
| FLL | Baltimore | June 26 to June 28 | $321 |
| DFW | Washington | June 27 to June 30 | $370 |
| BOS | Washington | June 27 to July 1 | $389 |
| BOS | Chantilly | June 27 to June 29 | $409 |
| LAX | Chantilly | June 27 to June 30 | $443 |
| LAX | Baltimore | June 27 to July 2 | $496 |
| LAX | Washington | June 27 to July 2 | $544 |
| SFO | Baltimore | June 27 to July 1 | $642 |
| SFO | Chantilly | June 27 to July 1 | $831 |
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
2951 Valley Avenue Winchester VA
$76 nightly
The price is $86 total per night from Jun 28 to Jun 29
$86 total
Jun 28 - Jun 29
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! (1,003 reviews)
"I was there for 5 nights and everything was perfect in every aspect of my stay."
Reviewed on Jun 22, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $75 total per night from Jun 28 to Jun 29
$75 total
Jun 28 - Jun 29
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! (1,053 reviews)
"Great experience. Staff was exceptional, room very clean, bed was new, very quiet and the price was reasonable. We will return."
Reviewed on Jun 23, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
$82 nightly
The price is $91 total per night from Jun 30 to Jul 1
$91 total
Jun 30 - Jul 1
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! (561 reviews)
"It was ok / the shower was good and the fridge worked"
Reviewed on Jun 23, 2026
Save an average of 15% on thousands of hotels when you're signed in
Royal Inn Motel
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
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
2951 Valley Avenue Winchester VA
$76 nightly
The price is $86 total per night from Jun 28 to Jun 29
$86 total
Jun 28 - Jun 29
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! (1,003 reviews)
"I was there for 5 nights and everything was perfect in every aspect of my stay."
Reviewed on Jun 22, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $75 total per night from Jun 28 to Jun 29
$75 total
Jun 28 - Jun 29
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! (1,053 reviews)
"Great experience. Staff was exceptional, room very clean, bed was new, very quiet and the price was reasonable. We will return."
Reviewed on Jun 23, 2026
Wayside Inn
7783 Main St Middletown VA
$144 nightly
The price is $159 total per night from Jun 28 to Jun 29
$159 total
Jun 28 - Jun 29
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! (438 reviews)
"A historical inn with charming features and friendly, helpful staff."
Reviewed on Jun 15, 2026
Save an average of 15% on thousands of hotels when you're signed in
Hotel Strasburg
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
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
141 Kernstown Commons Blvd Winchester VA
$95 nightly
The price is $103 total per night from Jul 26 to Jul 27
$103 total
Jul 26 - Jul 27
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! (1,000 reviews)
"The beds were hard as rocks"
Reviewed on Jun 21, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$118 nightly
The price is $131 total per night from Jul 1 to Jul 2
$131 total
Jul 1 - Jul 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)
"Very clean and welcoming. Room was comfortable, but the shear curtain had a large tear in it which we reported to the front desk and were thanked for brining it to their attention. You could see the person at the desk already writing up the report as we walked away. Coffee, tea, and ice water always ..."
Reviewed on Jun 23, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$95 nightly
The price is $106 total per night from Jul 12 to Jul 13
$106 total
Jul 12 - Jul 13
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! (1,004 reviews)
"Excellent place to stay."
Reviewed on Jun 24, 2026
Save an average of 15% on thousands of hotels when you're signed in
Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
$130 nightly
The price is $145 total per night from Jul 1 to Jul 2
$145 total
Jul 1 - Jul 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 ...
9/10 Wonderful! (1,007 reviews)
"Comfortable"
Reviewed on Jun 23, 2026
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.
Need a Car For After Your Flight?
Economy
Hanover, District of Columbia, USA
$37
$74 total
found 5 days ago
Compact
Hanover, District of Columbia, USA
$37
$74 total
found 5 days ago
Special
Hanover, District of Columbia, USA
$39
$117 total
found 5 days ago
Standard
Baltimore, Maryland, USA
$39
$117 total
found 5 days ago
Lowest prices found within the past 5 days. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
Plane Tickets To Winchester
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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!
More Ways To Wander
Winchester Hotels
Find the perfect hotel after your flight
Winchester Vacation Rentals
Great Deals on alternative accommodations
Winchester Car Rentals
Affordable cars to get you around town
Winchester Vacations
Save more by combining flights, hotels and cars
Things to do in Winchester
Activities, attractions and tours
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