Cheap Flights to Winchester from $35
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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 $65 and $35 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
$73 Roundtrip, just found
$73
Roundtrip
just found
FLL
Fort Lauderdale - Hollywood Intl.
IAD
Washington Dulles Intl.
$95 Roundtrip, found 6 days ago
$95
Roundtrip
found 6 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| CLT | Baltimore | September 24 to September 28 | $65 |
| ATL | Baltimore | October 14 to October 19 | $73 |
| FLL | Chantilly | November 10 to November 17 | $90 |
| BOS | Baltimore | September 29 to October 1 | $117 |
| MCO | Chantilly | September 14 to September 21 | $117 |
| DFW | Baltimore | September 23 to September 30 | $140 |
| ATL | Washington | November 7 to November 9 | $150 |
| DFW | Chantilly | September 22 to September 29 | $151 |
| CLT | Chantilly | October 21 to October 24 | $162 |
| CLT | Washington | November 26 to November 26 | $176 |
| FLL | Washington | November 10 to November 17 | $199 |
| DEN | Chantilly | October 24 to October 30 | $206 |
| LAX | Chantilly | October 27 to November 11 | $218 |
| LAX | Baltimore | October 17 to October 19 | $222 |
| SFO | Washington | October 19 to October 22 | $278 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | Chantilly | August 28 to September 15 | $155 |
| CLT | Chantilly | August 29 to August 31 | $274 |
| ATL | Chantilly | August 30 to September 6 | $307 |
| CLT | Washington | August 29 to September 1 | $354 |
| ATL | Washington | August 28 to August 29 | $357 |
| DFW | Washington | August 29 to August 31 | $365 |
| CLT | Baltimore | August 28 to August 30 | $375 |
| DFW | Baltimore | August 30 to September 2 | $385 |
| LAX | Chantilly | August 29 to September 12 | $422 |
| LAX | Washington | August 29 to September 9 | $443 |
| LAX | Baltimore | August 30 to September 3 | $456 |
| SFO | Chantilly | August 28 to September 13 | $461 |
| BOS | Washington | August 28 to August 31 | $461 |
| SFO | Washington | August 28 to September 13 | $466 |
| SFO | Baltimore | August 29 to September 6 | $476 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $65 |
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
$72 nightly
The price is $82 total per night from Sep 2 to Sep 3
$82 total
Sep 2 - Sep 3
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. ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $76 total per night from Aug 27 to Aug 28
$76 total
Aug 27 - Aug 28
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. ...
Twi-Lite Inn
53 West 14th Street Front Royal VA
$82 nightly
The price is $91 total per night from Aug 27 to Aug 28
$91 total
Aug 27 - Aug 28
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! (574 reviews)
"Good place. Only downside was i was not warned they would be replacing the roof at 8am, so i was woken up early due to the noise. Staff should notify guests for disturbances so that i can plan my sleep accordingly."
Reviewed on Aug 26, 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
$72 nightly
The price is $82 total per night from Sep 2 to Sep 3
$82 total
Sep 2 - Sep 3
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. ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $76 total per night from Aug 27 to Aug 28
$76 total
Aug 27 - Aug 28
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. ...
Wayside Inn
7783 Main St Middletown VA
$144 nightly
The price is $159 total per night from Aug 30 to Aug 31
$159 total
Aug 30 - Aug 31
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! (446 reviews)
"Clean room at a reasonable price. Interesting old inn."
Reviewed on Aug 11, 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
$94 nightly
The price is $105 total per night from Sep 20 to Sep 21
$105 total
Sep 20 - Sep 21
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 ...
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$118 nightly
The price is $131 total per night from Sep 2 to Sep 3
$131 total
Sep 2 - Sep 3
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. ...
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$84 nightly
The price is $94 total per night from Sep 2 to Sep 3
$94 total
Sep 2 - Sep 3
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! (1,000 reviews)
"We were pleasantly surprised and very pleased with this property. We enjoyed our overnight stay and would definitely stay again. Convenient to I-81, yet surprisingly quiet"
Reviewed on Aug 26, 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
$122 nightly
The price is $136 total per night from Sep 1 to Sep 2
$136 total
Sep 1 - Sep 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 ...
9.2/10 Wonderful! (1,022 reviews)
"Super clean, staff friendly. Perfect visit!"
Reviewed on Aug 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.
Winchester flight + hotel packages - business class 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
$30
$100 total
found 1 day ago
Compact
Hanover, District of Columbia, USA
$30
$100 total
found 1 day ago
Midsize
Hanover, District of Columbia, USA
$34
$110 total
found 1 day ago
Special
Hanover, District of Columbia, USA
$37
$118 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
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Things to do in Winchester
Activities, attractions and tours
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