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 $43 and $21 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.
$43 Roundtrip, found 6 hours ago
$43
Roundtrip
found 6 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Baltimore | September 22 to September 29 | $59 |
| FLL | Baltimore | September 30 to October 5 | $62 |
| ATL | Chantilly | September 11 to September 15 | $62 |
| BOS | Baltimore | October 21 to October 28 | $117 |
| BOS | Washington | September 17 to September 21 | $119 |
| DFW | Baltimore | November 10 to November 11 | $128 |
| DFW | Chantilly | September 29 to September 30 | $134 |
| ATL | Washington | October 27 to October 29 | $152 |
| FLL | Washington | September 5 to September 12 | $153 |
| LAX | Chantilly | September 26 to September 29 | $178 |
| LAX | Washington | November 11 to November 14 | $178 |
| LAX | Baltimore | October 13 to October 24 | $178 |
| CLT | Washington | October 30 to November 2 | $183 |
| SFO | Washington | November 4 to November 9 | $212 |
| FCO | Baltimore | September 17 to October 17 | $681 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Baltimore | August 23 to September 28 | $132 |
| FLL | Washington | August 22 to September 9 | $259 |
| FLL | Chantilly | August 22 to August 23 | $259 |
| ATL | Chantilly | August 23 to August 30 | $262 |
| ATL | Washington | August 23 to August 25 | $278 |
| FLL | Baltimore | August 21 to August 27 | $291 |
| CLT | Baltimore | August 23 to August 29 | $323 |
| DFW | Chantilly | August 22 to August 23 | $340 |
| CLT | Washington | August 22 to August 23 | $354 |
| LAX | Chantilly | August 23 to August 27 | $388 |
| LAX | Baltimore | August 22 to September 5 | $400 |
| LAX | Washington | August 23 to August 25 | $402 |
| SFO | Baltimore | August 23 to August 28 | $428 |
| SFO | Washington | August 22 to August 28 | $440 |
| BOS | Washington | August 21 to August 23 | $473 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $43 |
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
$72 nightly
The price is $82 total per night from Aug 19 to Aug 20
$82 total
Aug 19 - Aug 20
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. ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $76 total per night from Aug 16 to Aug 17
$76 total
Aug 16 - Aug 17
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. ...
Twi-Lite Inn
53 West 14th Street Front Royal VA
$82 nightly
The price is $91 total per night from Aug 16 to Aug 17
$91 total
Aug 16 - Aug 17
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
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
$72 nightly
The price is $82 total per night from Aug 19 to Aug 20
$82 total
Aug 19 - Aug 20
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. ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $76 total per night from Aug 16 to Aug 17
$76 total
Aug 16 - Aug 17
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. ...
Wayside Inn
7783 Main St Middletown VA
$144 nightly
The price is $159 total per night from Aug 16 to Aug 17
$159 total
Aug 16 - Aug 17
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
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
$96 nightly
The price is $107 total per night from Aug 30 to Aug 31
$107 total
Aug 30 - Aug 31
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)
"Staff is always nice and helpful. But rooms arent sparkling clean or well maintained. Better then some but not what it used to be."
Reviewed on Aug 10, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$105 nightly
The price is $117 total per night from Aug 23 to Aug 24
$117 total
Aug 23 - Aug 24
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. ...
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$84 nightly
The price is $94 total per night from Aug 20 to Aug 21
$94 total
Aug 20 - Aug 21
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! (1,001 reviews)
"Nice breakfast, convenient location and helpful staff."
Reviewed on Aug 13, 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
$122 nightly
The price is $136 total per night from Aug 23 to Aug 24
$136 total
Aug 23 - Aug 24
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! (1,015 reviews)
"This is the 2nd year we have stayed at your hotel. Your location, cleanliness, & service is great for our needs."
Reviewed on Aug 12, 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.
Winchester flight + hotel packages - premium economy flights
Price found within the past 48 hours. Click for updated prices.
Winchester flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Compact SUV
Baltimore, Maryland, USA
$41
$121 total
found 2 days ago
Midsize SUV
Baltimore, Maryland, USA
$43
$127 total
found 2 days ago
Standard SUV
Baltimore, Maryland, USA
$45
$131 total
found 2 days ago
Mini Van
Hanover, District of Columbia, USA
$46
$135 total
found 4 days ago
Lowest prices found within the past 2 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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