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 $53 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.
IAD
Washington Dulles Intl.
$53 Roundtrip, found 3 days ago
$53
Roundtrip
found 3 days ago
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, just found
$56
Roundtrip
just found
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Baltimore | March 10 to March 16 | $56 |
| BOS | Baltimore | April 25 to May 2 | $98 |
| FLL | Washington | May 13 to May 18 | $127 |
| ATL | Washington | April 15 to April 22 | $137 |
| LAX | Baltimore | April 21 to April 28 | $144 |
| CLT | Chantilly | April 17 to April 19 | $160 |
| BOS | Washington | May 11 to May 15 | $167 |
| DFW | Washington | March 3 to March 4 | $168 |
| BOS | Chantilly | May 4 to May 6 | $177 |
| LAX | Washington | March 4 to March 5 | $187 |
| LAX | Chantilly | April 22 to April 25 | $200 |
| SFO | Baltimore | March 10 to March 17 | $200 |
| SFO | Chantilly | April 17 to April 20 | $210 |
| FCO | Chantilly | March 25 to April 18 | $477 |
| FCO | Baltimore | April 29 to May 16 | $603 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | Baltimore | February 15 to March 9 | $96 |
| SFO | Washington | February 15 to March 4 | $244 |
| CLT | Chantilly | February 15 to February 23 | $264 |
| DFW | Baltimore | February 14 to February 21 | $276 |
| DFW | Washington | February 15 to February 22 | $296 |
| BOS | Chantilly | February 14 to February 18 | $304 |
| BOS | Washington | February 15 to February 18 | $321 |
| CLT | Washington | February 15 to February 24 | $329 |
| SFO | Baltimore | February 14 to March 14 | $361 |
| LAX | Chantilly | February 13 to February 15 | $372 |
| SFO | Chantilly | February 14 to February 16 | $382 |
| DEN | Washington | February 14 to February 18 | $414 |
| LAX | Washington | February 13 to February 14 | $437 |
| ATL | Washington | February 13 to February 19 | $465 |
| LAX | Baltimore | February 14 to February 18 | $512 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $53 |
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 13 to Feb 14
$77 total
Feb 13 - Feb 14
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! (1,002 reviews)
Went here because it had higher ratings than an other Motel 6 and was curious. But it's um...a Motel 6. Came in around 8 to a large motel with maybe a dozen cars in the lot. Still the clerk had crammed all the guests in the back near a trash-laden forest. TV playing through the walls. Just thoughtless. ...
Reviewed on Jan 10, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$70 nightly
The price is $76 total per night from Feb 12 to Feb 13
$76 total
Feb 12 - Feb 13
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! (1,083 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
$58 nightly
The price is $65 total per night from Feb 12 to Feb 13
$65 total
Feb 12 - Feb 13
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
$68 nightly
The price is $77 total per night from Feb 13 to Feb 14
$77 total
Feb 13 - Feb 14
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! (1,002 reviews)
Went here because it had higher ratings than an other Motel 6 and was curious. But it's um...a Motel 6. Came in around 8 to a large motel with maybe a dozen cars in the lot. Still the clerk had crammed all the guests in the back near a trash-laden forest. TV playing through the walls. Just thoughtless. ...
Reviewed on Jan 10, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$70 nightly
The price is $76 total per night from Feb 12 to Feb 13
$76 total
Feb 12 - Feb 13
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! (1,083 reviews)
Room was good for the price, staff was friendly and helpful
Reviewed on Feb 4, 2026
Wayside Inn
7783 Main St Middletown VA
$89 nightly
The price is $98 total per night from Feb 12 to Feb 13
$98 total
Feb 12 - Feb 13
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 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
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
$83 nightly
The price is $90 total per night from Feb 22 to Feb 23
$90 total
Feb 22 - Feb 23
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)
the room was very comfortable and the hot breakfast was great. the hotel maintenance guy, Steve, was very helpful in offering to jumpstart our car the next morning when it wouldn't start. the only issue was that the TV was set in Spanish and no one could get it reset to be in English.
Reviewed on Feb 9, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$113 nightly
The price is $126 total per night from Feb 18 to Feb 19
$126 total
Feb 18 - Feb 19
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)
We stay here every year on our way to NC. Always very nice and helpful staff.
Reviewed on Jan 23, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$84 nightly
The price is $92 total per night from Feb 17 to Feb 18
$92 total
Feb 17 - Feb 18
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)
Very clean
Reviewed on Feb 10, 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 Feb 22 to Feb 23
$109 total
Feb 22 - Feb 23
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)
Very nice breakfast (eggs sausage, potatoes, ...), clean lobby, and all the staff was friendly, including Beatrix. Also we appreciated the attention to a clean and warm pool room on a very cold January. Great mexican 1 mile away at Potrillo's.
Reviewed on Jan 20, 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 Minneapolis to Winchester
View all tripsWinchester flight + hotel packages - first class flights
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View all tripsNeed a Car For After Your Flight?
Economy
Hanover, District of Columbia, USA
$20
$40 total
found 2 days ago
Compact
Hanover, District of Columbia, USA
$20
$40 total
found 2 days ago
Standard
Baltimore, Maryland, USA
$24
$80 total
found 2 days ago
Fullsize
Baltimore, Maryland, USA
$25
$83 total
found 2 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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