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 $57 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
$57 Roundtrip, found 19 hours ago
$57
Roundtrip
found 19 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | April 21 to April 28 | $57 |
| FLL | Baltimore | May 15 to May 16 | $66 |
| CLT | Baltimore | May 6 to May 11 | $98 |
| DFW | Baltimore | April 28 to May 5 | $121 |
| FLL | Washington | May 28 to June 1 | $131 |
| ATL | Washington | May 7 to May 10 | $160 |
| CLT | Chantilly | May 9 to May 10 | $161 |
| SFO | Washington | April 14 to April 18 | $161 |
| LAX | Baltimore | April 21 to April 22 | $161 |
| LAX | Washington | April 7 to April 28 | $175 |
| DFW | Washington | April 14 to April 17 | $182 |
| CLT | Washington | April 7 to April 11 | $198 |
| SFO | Baltimore | April 14 to April 18 | $202 |
| FCO | Chantilly | April 23 to April 26 | $517 |
| FCO | Baltimore | April 19 to May 5 | $593 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | March 14 to April 4 | $238 |
| FLL | Chantilly | March 14 to March 21 | $258 |
| CLT | Chantilly | March 14 to March 21 | $277 |
| LAX | Chantilly | March 13 to March 23 | $319 |
| BOS | Washington | March 15 to March 16 | $328 |
| CLT | Baltimore | March 14 to March 16 | $330 |
| BOS | Chantilly | March 15 to March 22 | $338 |
| DFW | Baltimore | March 13 to March 16 | $385 |
| FLL | Washington | March 13 to March 16 | $389 |
| LAX | Baltimore | March 15 to March 18 | $423 |
| SFO | Washington | March 13 to March 16 | $463 |
| LAX | Washington | March 13 to March 16 | $487 |
| BOS | Baltimore | March 14 to March 29 | $545 |
| ATL | Washington | March 14 to March 16 | $614 |
| SFO | Chantilly | March 15 to March 18 | $688 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $57 |
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 12 to Mar 13
$77 total
Mar 12 - Mar 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. ...
8.2/10 Very Good! (1,001 reviews)
Room clean and staff was nice
Reviewed on Feb 25, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$67 nightly
The price is $72 total per night from Mar 12 to Mar 13
$72 total
Mar 12 - Mar 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! (1,080 reviews)
Quick overnight. Good breakfast.
Reviewed on Mar 10, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
$72 nightly
The price is $80 total per night from Mar 11 to Mar 12
$80 total
Mar 11 - Mar 12
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 12 to Mar 13
$77 total
Mar 12 - Mar 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. ...
8.2/10 Very Good! (1,001 reviews)
Room clean and staff was nice
Reviewed on Feb 25, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$67 nightly
The price is $72 total per night from Mar 12 to Mar 13
$72 total
Mar 12 - Mar 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! (1,080 reviews)
Quick overnight. Good breakfast.
Reviewed on Mar 10, 2026
Wayside Inn
7783 Main St Middletown VA
$89 nightly
The price is $98 total per night from Mar 11 to Mar 12
$98 total
Mar 11 - Mar 12
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! (425 reviews)
Old building but clean and very comfortable. Perfect spot and price.
Reviewed on Mar 9, 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 22 to Mar 23
$99 total
Mar 22 - Mar 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! (1,002 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 14 to Mar 15
$126 total
Mar 14 - Mar 15
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! (1,004 reviews)
Nice rooms
Reviewed on Mar 6, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$84 nightly
The price is $92 total per night from Mar 22 to Mar 23
$92 total
Mar 22 - Mar 23
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! (1,004 reviews)
An excellent motel for short-term stays. Very friendly and helpful staff at the reception desk, good breakfast choices, wonderful room with king bed. I highly recommend it. This was an excellent Quality Inn. On the same trip we stayed at another Quality Inn in another city, and it was so bad compared ...
Reviewed on Mar 8, 2026
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Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
$103 nightly
The price is $114 total per night from Mar 29 to Mar 30
$114 total
Mar 29 - Mar 30
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! (1,003 reviews)
Staff was very friendly and the room was very clean.
Reviewed on Mar 8, 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
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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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Need a Car For After Your Flight?
Economy
Hanover, District of Columbia, USA
$25
$50 total
found 1 day ago
Compact
Hanover, District of Columbia, USA
$25
$50 total
found 1 day 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
Frequently asked questions
Plane Tickets To Winchester
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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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