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
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, found 2 hours ago
$56
Roundtrip
found 2 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | March 10 to March 11 | $56 |
| ATL | Baltimore | April 18 to April 20 | $56 |
| FLL | Baltimore | April 20 to April 26 | $56 |
| DFW | Chantilly | April 23 to April 30 | $88 |
| DFW | Baltimore | April 22 to April 29 | $88 |
| BOS | Baltimore | April 25 to May 2 | $98 |
| ATL | Washington | May 5 to May 9 | $137 |
| FLL | Chantilly | April 23 to April 26 | $137 |
| LAX | Washington | May 6 to May 12 | $144 |
| SFO | Washington | April 21 to April 25 | $144 |
| BOS | Chantilly | May 8 to May 10 | $160 |
| BOS | Washington | April 14 to April 14 | $172 |
| SFO | Chantilly | April 28 to May 6 | $178 |
| DFW | Washington | April 25 to April 26 | $180 |
| SFO | Baltimore | April 24 to April 27 | $200 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Baltimore | February 21 to February 23 | $216 |
| FLL | Baltimore | February 20 to February 22 | $232 |
| DFW | Baltimore | February 21 to February 25 | $265 |
| ATL | Chantilly | February 22 to February 26 | $268 |
| CLT | Chantilly | February 21 to February 26 | $284 |
| LAX | Baltimore | February 21 to February 23 | $316 |
| LAX | Washington | February 22 to February 24 | $343 |
| ATL | Washington | February 20 to February 21 | $344 |
| DFW | Washington | February 21 to February 23 | $346 |
| CLT | Washington | February 20 to February 27 | $360 |
| LAX | Chantilly | February 21 to February 23 | $377 |
| SFO | Chantilly | February 20 to February 22 | $377 |
| SFO | Washington | February 20 to February 22 | $397 |
| SFO | Baltimore | February 21 to February 24 | $439 |
| FBT | Washington | February 20 to February 23 | $446 |
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
$68 nightly
The price is $77 total per night from Feb 20 to Feb 21
$77 total
Feb 20 - Feb 21
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. ...
8.2/10 Very Good! (1,001 reviews)
There were roaches in the room and blood stains on the sheets. Also staff was disrespectful and rude. I asked for a refund and was denied
Reviewed on Feb 16, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$71 nightly
The price is $77 total per night from Feb 20 to Feb 21
$77 total
Feb 20 - Feb 21
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! (1,084 reviews)
Room was good for the price, staff was friendly and helpful
Reviewed on Feb 4, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
$62 nightly
The price is $69 total per night from Feb 19 to Feb 20
$69 total
Feb 19 - Feb 20
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 ...
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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 Feb 20 to Feb 21
$77 total
per night
Feb 20 - Feb 21
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! (1,001 reviews)
There were roaches in the room and blood stains on the sheets. Also staff was disrespectful and rude. I asked for a refund and was denied
Reviewed on Feb 16, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is $77 total per night from Feb 20 to Feb 21
$77 total
per night
Feb 20 - Feb 21
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! (1,084 reviews)
Room was good for the price, staff was friendly and helpful
Reviewed on Feb 4, 2026
Wayside Inn
7783 Main St Middletown VA
The price is $98 total per night from Feb 19 to Feb 20
$98 total
per night
Feb 19 - Feb 20
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! (422 reviews)
Room 14 was great for spirit activity as well as the rest of the property! Highly recommend ghost hunters to explore the inn. Food at their Larick’s tavern was delish!! Overall service and staff were knowledgeable and friendly! We had a great experience for our anniversary!
Reviewed on Jan 31, 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
$85 nightly
The price is $92 total per night from Feb 24 to Feb 25
$92 total
Feb 24 - Feb 25
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! (1,001 reviews)
Nice clean room. Quiet. Nice pool. Good breakfast. We stay at country inn and suites whenever there is one …. Lancaster……..Wheeling. They are all great
Reviewed on Feb 16, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$113 nightly
The price is $126 total per night from Feb 25 to Feb 26
$126 total
Feb 25 - Feb 26
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)
Yes
Reviewed on Feb 15, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$84 nightly
The price is $92 total per night from Feb 24 to Feb 25
$92 total
Feb 24 - Feb 25
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 ...
9.2/10 Wonderful! (1,000 reviews)
nice room. good staff. worth it.
Reviewed on Feb 17, 2026
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Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
$98 nightly
The price is $109 total per night from Mar 1 to Mar 2
$109 total
Mar 1 - Mar 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! (1,001 reviews)
Just an average hotel
Reviewed on Feb 17, 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 - 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
$23
$46 total
found 2 days ago
Compact
Hanover, District of Columbia, USA
$23
$46 total
found 2 days ago
Midsize
Hanover, District of Columbia, USA
$34
$68 total
found 1 day ago
Special
Hanover, District of Columbia, USA
$37
$74 total
found 1 day 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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