Cheap Flights to Winchester from $33
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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 $33 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.
$57 Roundtrip, found 3 hours ago
$57
Roundtrip
found 3 hours ago
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$76 Roundtrip, found 21 hours ago
$76
Roundtrip
found 21 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | May 5 to May 5 | $62 |
| FLL | Baltimore | April 30 to May 9 | $65 |
| ATL | Baltimore | June 10 to June 16 | $66 |
| FLL | Chantilly | May 21 to May 25 | $66 |
| DFW | Baltimore | June 3 to June 10 | $79 |
| CLT | Baltimore | May 7 to May 11 | $94 |
| BOS | Baltimore | April 25 to May 2 | $97 |
| DFW | Chantilly | June 3 to June 10 | $102 |
| BOS | Washington | June 24 to July 1 | $117 |
| ATL | Washington | June 10 to June 16 | $169 |
| LAX | Baltimore | April 28 to May 5 | $170 |
| FLL | Washington | June 5 to June 8 | $180 |
| SFO | Baltimore | April 27 to April 29 | $193 |
| CLT | Washington | May 6 to May 9 | $209 |
| SFO | Chantilly | June 7 to June 10 | $215 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | April 11 to April 27 | $167 |
| CLT | Baltimore | April 10 to April 13 | $218 |
| ATL | Baltimore | April 12 to April 14 | $220 |
| BOS | Chantilly | April 11 to April 14 | $250 |
| CLT | Chantilly | April 10 to April 13 | $251 |
| FLL | Chantilly | April 11 to April 14 | $251 |
| DFW | Baltimore | April 12 to April 14 | $331 |
| DFW | Chantilly | April 11 to April 13 | $335 |
| BOS | Washington | April 11 to April 14 | $336 |
| LAX | Baltimore | April 10 to April 13 | $347 |
| ATL | Washington | April 11 to April 13 | $366 |
| LAX | Washington | April 11 to April 13 | $390 |
| LAX | Chantilly | April 10 to April 12 | $459 |
| FCO | Chantilly | April 10 to April 24 | $625 |
| SFO | Chantilly | April 11 to April 14 | $694 |
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 Apr 8 to Apr 9
$77 total
Apr 8 - Apr 9
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)
Had to switch room b/c door latch was broken and a ROACH came out the woodworks and was crawling on the bed!
Reviewed on Mar 29, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$71 nightly
The price is $77 total per night from Apr 8 to Apr 9
$77 total
Apr 8 - Apr 9
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! (1,077 reviews)
There was a busy area for breakfast but many choices nearby.
Reviewed on Apr 5, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
$75 nightly
The price is $83 total per night from Apr 8 to Apr 9
$83 total
Apr 8 - Apr 9
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! (549 reviews)
The beds were comfy and pillows. The room is very old and dated. The bathroom towel rack is broken in the bathtub and soap holder. Coffee pot leaked all over the table. It was way over priced for the looks of the place inside and out. It is very run down. The building going into the office needs ...
Reviewed on Apr 6, 2026
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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 Apr 8 to Apr 9
$77 total
Apr 8 - Apr 9
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)
Had to switch room b/c door latch was broken and a ROACH came out the woodworks and was crawling on the bed!
Reviewed on Mar 29, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$71 nightly
The price is $77 total per night from Apr 8 to Apr 9
$77 total
Apr 8 - Apr 9
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! (1,077 reviews)
There was a busy area for breakfast but many choices nearby.
Reviewed on Apr 5, 2026
Wayside Inn
7783 Main St Middletown VA
$144 nightly
The price is $159 total per night from Apr 12 to Apr 13
$159 total
Apr 12 - Apr 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 Cedar ...
9.2/10 Wonderful! (426 reviews)
Nostalgia and history are prime attractions of this lovely inn. The barkeep Justin was friendly and helpful
Reviewed on Mar 16, 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
$95 nightly
The price is $103 total per night from May 3 to May 4
$103 total
May 3 - May 4
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! (1,000 reviews)
The room was clean. The breakfast was well stocked and the attendants kept in very clean.
Reviewed on Mar 31, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$113 nightly
The price is $126 total per night from Apr 22 to Apr 23
$126 total
Apr 22 - Apr 23
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! (1,006 reviews)
Hotel was clean and the staff very friendly. The location is convenient, close to the highway and places to eat nearby as well.
Reviewed on Apr 7, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$92 nightly
The price is $100 total per night from May 5 to May 6
$100 total
May 5 - May 6
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)
Good
Reviewed on Apr 4, 2026
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Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
$102 nightly
The price is $114 total per night from Apr 26 to Apr 27
$114 total
Apr 26 - Apr 27
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! (1,002 reviews)
Clean and friendly staff. However, room was not ready for check in at 7 pm, and not enough seating for breakfast at Saturday morning.
Reviewed on Apr 4, 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
$46
$92 total
found 1 day ago
Compact
Hanover, District of Columbia, USA
$46
$92 total
found 1 day ago
Midsize
Hanover, District of Columbia, USA
$49
$98 total
found 1 day ago
Special
Hanover, District of Columbia, USA
$52
$104 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
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Things to do in Winchester
Activities, attractions and tours
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