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 17 hours ago
$56
Roundtrip
found 17 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | March 28 to April 4 | $57 |
| ATL | Baltimore | April 29 to May 3 | $62 |
| FLL | Baltimore | May 9 to May 10 | $66 |
| CLT | Baltimore | May 5 to May 18 | $84 |
| DFW | Baltimore | May 5 to May 9 | $99 |
| BOS | Baltimore | May 5 to May 5 | $107 |
| ATL | Washington | April 18 to April 22 | $137 |
| FLL | Washington | May 8 to May 12 | $137 |
| LAX | Baltimore | April 28 to May 5 | $144 |
| SFO | Washington | April 21 to April 22 | $145 |
| DFW | Chantilly | April 15 to April 20 | $147 |
| BOS | Washington | April 14 to April 16 | $157 |
| CLT | Chantilly | April 10 to April 13 | $160 |
| DFW | Washington | May 2 to May 6 | $180 |
| FCO | Baltimore | April 17 to April 20 | $592 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | March 7 to March 16 | $123 |
| MCO | Chantilly | March 6 to March 8 | $235 |
| FLL | Baltimore | March 7 to March 11 | $235 |
| DFW | Baltimore | March 7 to March 10 | $258 |
| CLT | Baltimore | March 6 to March 7 | $258 |
| ATL | Baltimore | March 8 to March 12 | $267 |
| BOS | Chantilly | March 7 to March 9 | $297 |
| DFW | Chantilly | March 7 to March 11 | $309 |
| BOS | Washington | March 8 to March 11 | $321 |
| FLL | Washington | March 7 to March 10 | $328 |
| BOS | Baltimore | March 7 to March 9 | $368 |
| CLT | Washington | March 6 to March 13 | $384 |
| SFO | Washington | March 7 to March 21 | $392 |
| LAX | Washington | March 7 to March 14 | $439 |
| SFO | Chantilly | March 6 to March 9 | $674 |
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 Mar 7 to Mar 8
$77 total
Mar 7 - Mar 8
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! (1,000 reviews)
Room clean and staff was nice
Reviewed on Feb 25, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$68 nightly
The price is $74 total per night from Mar 6 to Mar 7
$74 total
Mar 6 - Mar 7
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! (1,078 reviews)
Room was spacious, bed was comfortable and lots of TV channels. Gentleman that checked us in and out was very courteous.
Reviewed on Feb 24, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
$72 nightly
The price is $80 total per night from Mar 5 to Mar 6
$80 total
Mar 5 - Mar 6
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! (546 reviews)
Room was clean and fresh. Bed and sheets were nice
Reviewed on Mar 1, 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
$68 nightly
The price is $77 total per night from Mar 7 to Mar 8
$77 total
Mar 7 - Mar 8
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! (1,000 reviews)
Room clean and staff was nice
Reviewed on Feb 25, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$68 nightly
The price is $74 total per night from Mar 6 to Mar 7
$74 total
Mar 6 - Mar 7
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! (1,078 reviews)
Room was spacious, bed was comfortable and lots of TV channels. Gentleman that checked us in and out was very courteous.
Reviewed on Feb 24, 2026
Wayside Inn
7783 Main St Middletown VA
$89 nightly
The price is $98 total per night from Mar 5 to Mar 6
$98 total
Mar 5 - Mar 6
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! (424 reviews)
Interesting unique place. We explored the different rooms, will definitely be back. With ghost hunting equipment.
Reviewed on Feb 26, 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
$91 nightly
The price is $99 total per night from Mar 15 to Mar 16
$99 total
Mar 15 - Mar 16
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! (1,002 reviews)
Convenient location, clean room, and nice breakfast
Reviewed on Mar 1, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$113 nightly
The price is $126 total per night from Mar 11 to Mar 12
$126 total
Mar 11 - Mar 12
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! (1,003 reviews)
We were told there wasn’t many people staying on property but we received a room with dirty sheets, stuff on the wall, and the mirror cracked.
Reviewed on Mar 2, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$84 nightly
The price is $92 total per night from Mar 10 to Mar 11
$92 total
Mar 10 - Mar 11
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! (1,002 reviews)
Everything was perfect. Would highly recommend this hotel
Reviewed on Mar 2, 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
$98 nightly
The price is $109 total per night from Mar 15 to Mar 16
$109 total
Mar 15 - Mar 16
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! (1,000 reviews)
Great one night stay! Friendly, welcoming staff! Room was clean and comfortable. Location was perfect- near dining and highway!
Reviewed on Feb 27, 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.
Don't see what you're looking for?
See all available trips from Minneapolis to Winchester
View all tripsNeed a Car For After Your Flight?
Economy
Hanover, District of Columbia, USA
$25
$50 total
found 3 hours ago
Compact
Hanover, District of Columbia, USA
$25
$50 total
found 3 hours ago
Midsize
Hanover, District of Columbia, USA
$34
$68 total
found 3 hours ago
Special
Hanover, District of Columbia, USA
$37
$74 total
found 3 hours ago
Lowest prices found within the past 3 hours. 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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