Cheap Flights to Winchester from $34
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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 $57 and $34 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$75 Roundtrip, found 5 days ago
$75
Roundtrip
found 5 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | April 22 to April 29 | $57 |
| ATL | Baltimore | April 25 to April 28 | $68 |
| FLL | Chantilly | June 2 to June 3 | $80 |
| FLL | Baltimore | April 15 to April 26 | $95 |
| BOS | Baltimore | May 12 to May 12 | $97 |
| BOS | Washington | May 12 to May 12 | $141 |
| ATL | Washington | April 21 to April 23 | $163 |
| DFW | Washington | April 14 to May 5 | $166 |
| FLL | Washington | April 15 to April 21 | $166 |
| LAX | Washington | April 15 to April 21 | $166 |
| LAX | Baltimore | April 28 to May 5 | $170 |
| SFO | Baltimore | April 13 to April 22 | $176 |
| LAX | Chantilly | May 2 to May 5 | $203 |
| FCO | Chantilly | April 14 to April 20 | $520 |
| FCO | Baltimore | April 19 to May 5 | $587 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | Baltimore | March 27 to April 7 | $126 |
| ATL | Baltimore | March 27 to March 31 | $174 |
| ATL | Chantilly | March 29 to April 18 | $196 |
| CLT | Chantilly | March 28 to April 4 | $245 |
| DFW | Chantilly | March 27 to March 31 | $276 |
| DEN | Chantilly | March 29 to April 1 | $280 |
| ATL | Washington | March 27 to March 28 | $313 |
| BOS | Washington | March 29 to April 1 | $321 |
| CLT | Baltimore | March 28 to March 30 | $348 |
| DFW | Washington | March 27 to March 31 | $349 |
| CLT | Washington | March 28 to April 4 | $388 |
| SFO | Washington | March 28 to April 8 | $437 |
| SFO | Chantilly | March 29 to April 30 | $594 |
| FCO | Chantilly | March 29 to April 12 | $627 |
| FCO | Baltimore | March 27 to April 12 | $1,024 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $57 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, 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
2951 Valley Avenue Winchester VA
The price is $77 total per night from Mar 25 to Mar 26
$77 total
per night
Mar 25 - Mar 26
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. ...
8.2/10 Very Good! (1,000 reviews)
Room clean and staff was nice
Reviewed on Feb 25, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is $73 total per night from Mar 27 to Mar 28
$73 total
per night
Mar 27 - Mar 28
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)
Neat
Reviewed on Mar 22, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
The price is $80 total per night from Mar 25 to Mar 26
$80 total
per night
Mar 25 - Mar 26
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! (548 reviews)
Honestly everything was very well kept. Room was pretty clean only two small hairs we found on a pillow. Fridge worked great and the air conditioning/ heater was also great. Short drive to the Shenandoah entrance
Reviewed on Mar 22, 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 Blue Ridge Arts Council and Gallery and Front ...
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
The price is $77 total per night from Mar 25 to Mar 26
$77 total
per night
Mar 25 - Mar 26
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. ...
8.2/10 Very Good! (1,000 reviews)
Room clean and staff was nice
Reviewed on Feb 25, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is $73 total per night from Mar 27 to Mar 28
$73 total
per night
Mar 27 - Mar 28
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)
Neat
Reviewed on Mar 22, 2026
Wayside Inn
7783 Main St Middletown VA
The price is $98 total per night from Mar 25 to Mar 26
$98 total
per night
Mar 25 - Mar 26
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! (426 reviews)
Nostalgia and history are prime attractions of this lovely inn. The barkeep Justin was friendly and helpful
Reviewed on Mar 16, 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
The price is $99 total per night from Apr 13 to Apr 14
$99 total
per night
Apr 13 - Apr 14
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! (1,004 reviews)
The room was clean and the staff was friendly. It was a convenient stop for our continuing trip.
Reviewed on Mar 22, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
The price is $126 total per night from Apr 3 to Apr 4
$126 total
per night
Apr 3 - Apr 4
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)
Asked for quiet floor after a long week of travels for work and he put me on the 4th floor Was super quiet , super clean and breakfast was decent,
Reviewed on Mar 16, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
The price is $96 total per night from Mar 30 to Mar 31
$96 total
per night
Mar 30 - Mar 31
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! (1,004 reviews)
Updated and clean. Great deal !
Reviewed on Mar 20, 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
The price is $113 total per night from Apr 12 to Apr 13
$113 total
per night
Apr 12 - Apr 13
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! (1,004 reviews)
Just passing thru, clean room.
Reviewed on Mar 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.
Winchester flight + hotel packages - premium economy flights
Price found within the past 48 hours. Click for updated prices.
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See all available trips from Los Angeles to Winchester
View all tripsWinchester flight + hotel packages - first class 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
$31
$62 total
found 1 day ago
Compact
Hanover, District of Columbia, USA
$31
$62 total
found 1 day ago
Midsize
Hanover, District of Columbia, USA
$35
$70 total
found 1 day ago
Standard
Baltimore, Maryland, USA
$36
$110 total
found 1 day ago
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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