Cheap Flights to Winchester from $28
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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 $56 and $28 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, found 2 days ago
$56
Roundtrip
found 2 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Baltimore | August 12 to August 18 | $60 |
| FLL | Chantilly | August 25 to August 26 | $77 |
| CLT | Baltimore | July 27 to July 27 | $105 |
| BOS | Washington | July 15 to July 28 | $110 |
| BOS | Baltimore | July 14 to July 15 | $112 |
| DFW | Baltimore | September 6 to September 6 | $155 |
| FLL | Washington | August 11 to August 12 | $157 |
| ATL | Washington | September 9 to September 29 | $169 |
| DFW | Chantilly | September 6 to September 6 | $170 |
| CLT | Chantilly | September 3 to September 7 | $217 |
| CLT | Washington | September 3 to September 7 | $233 |
| LAX | Baltimore | July 16 to July 23 | $258 |
| LAX | Chantilly | September 1 to September 9 | $258 |
| SFO | Washington | September 16 to September 23 | $269 |
| FCO | Baltimore | September 10 to September 15 | $710 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | Chantilly | June 20 to June 23 | $195 |
| FLL | Baltimore | June 19 to June 23 | $255 |
| BOS | Baltimore | June 20 to June 22 | $268 |
| CLT | Chantilly | June 20 to June 26 | $270 |
| BOS | Chantilly | June 20 to June 22 | $278 |
| FLL | Washington | June 20 to June 23 | $290 |
| DFW | Baltimore | June 20 to June 20 | $358 |
| DFW | Washington | June 19 to June 22 | $370 |
| LAX | Chantilly | June 20 to June 23 | $375 |
| DFW | Chantilly | June 20 to June 24 | $376 |
| BOS | Washington | June 20 to June 22 | $399 |
| LAX | Washington | June 20 to July 4 | $406 |
| LAX | Baltimore | June 19 to June 24 | $594 |
| SFO | Chantilly | June 19 to July 12 | $632 |
| SFO | Baltimore | June 20 to June 24 | $639 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $56 |
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 21 to Jun 22
$86 total
Jun 21 - Jun 22
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! (1,007 reviews)
"very pet friendly, large area for dogs, well lighted parking"
Reviewed on Jun 9, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$71 nightly
The price is $77 total per night from Jun 18 to Jun 19
$77 total
Jun 18 - Jun 19
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! (1,071 reviews)
"We really liked our stay in Winchester, and the hotel was in a good location for us on our travels. It was clean the, and the breakfast hostess was awesome. 😊"
Reviewed on Jun 17, 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! (558 reviews)
"Very old and outdated place"
Reviewed on Jun 14, 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
$76 nightly
The price is $86 total per night from Jun 21 to Jun 22
$86 total
Jun 21 - Jun 22
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! (1,007 reviews)
"very pet friendly, large area for dogs, well lighted parking"
Reviewed on Jun 9, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$71 nightly
The price is $77 total per night from Jun 18 to Jun 19
$77 total
Jun 18 - Jun 19
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! (1,071 reviews)
"We really liked our stay in Winchester, and the hotel was in a good location for us on our travels. It was clean the, and the breakfast hostess was awesome. 😊"
Reviewed on Jun 17, 2026
Wayside Inn
7783 Main St Middletown VA
$144 nightly
The price is $159 total per night from Jun 21 to Jun 22
$159 total
Jun 21 - Jun 22
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
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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 8 to Jul 9
$103 total
Jul 8 - Jul 9
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)
"Location is great, near popular restaurants. Bed was so comfortable! Staff was very friendly and helpful."
Reviewed on Jun 15, 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! (1,006 reviews)
"Standard hotel. Neither excellent nor lacking."
Reviewed on Jun 7, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$93 nightly
The price is $101 total per night from Jun 28 to Jun 29
$101 total
Jun 28 - Jun 29
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! (1,002 reviews)
"Could use some updating but it was clean and comfortable, breakfast was exceptional. Front desk, he was so friendly and nice"
Reviewed on Jun 17, 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 Jun 28 to Jun 29
$145 total
Jun 28 - Jun 29
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! (1,009 reviews)
"Very new and clean. Hot breakfast was good."
Reviewed on Jun 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?
Economy
Hanover, District of Columbia, USA
$47
$94 total
found 4 days ago
Compact
Hanover, District of Columbia, USA
$47
$94 total
found 4 days ago
Midsize
Hanover, District of Columbia, USA
$51
$102 total
found 4 days ago
Special
Hanover, District of Columbia, USA
$54
$108 total
found 4 days ago
Lowest prices found within the past 4 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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