Cheap Flights to Winchester from $41
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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 $61 and $41 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.
IAD
Washington Dulles Intl.
$66 Roundtrip, found 6 days ago
$66
Roundtrip
found 6 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Baltimore | September 22 to September 22 | $61 |
| CLT | Baltimore | September 3 to September 6 | $74 |
| ATL | Chantilly | September 9 to September 14 | $80 |
| BOS | Washington | August 12 to August 19 | $100 |
| DFW | Baltimore | October 13 to October 20 | $138 |
| CLT | Chantilly | August 12 to August 17 | $163 |
| CLT | Washington | August 15 to August 18 | $163 |
| BOS | Chantilly | September 3 to September 6 | $165 |
| ATL | Washington | August 19 to August 22 | $169 |
| FLL | Washington | August 15 to August 22 | $207 |
| DAL | Washington | September 22 to October 6 | $227 |
| LAX | Chantilly | October 27 to November 2 | $227 |
| LAX | Washington | October 26 to October 29 | $237 |
| SFO | Baltimore | August 20 to August 24 | $258 |
| FCO | Baltimore | October 9 to October 13 | $733 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Baltimore | July 25 to July 29 | $173 |
| FLL | Chantilly | July 25 to July 27 | $243 |
| ATL | Chantilly | July 24 to July 25 | $262 |
| ATL | Washington | July 25 to July 28 | $276 |
| CLT | Chantilly | July 25 to July 27 | $281 |
| FLL | Washington | July 25 to August 2 | $295 |
| DFW | Chantilly | July 25 to July 25 | $364 |
| BOS | Washington | July 25 to August 1 | $401 |
| LAX | Baltimore | July 26 to July 27 | $478 |
| LAX | Washington | July 25 to July 29 | $502 |
| LAX | Chantilly | July 24 to July 27 | $508 |
| SFO | Baltimore | July 25 to July 31 | $657 |
| SFO | Washington | July 25 to July 31 | $692 |
| FCO | Chantilly | July 25 to July 27 | $787 |
| SFO | Chantilly | July 24 to July 27 | $799 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $61 |
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
$59 nightly
The price is $66 total per night from Jul 30 to Jul 31
$66 total
Jul 30 - Jul 31
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
$70 nightly
The price is $77 total per night from Jul 23 to Jul 24
$77 total
Jul 23 - Jul 24
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 4 to Aug 5
$91 total
Aug 4 - Aug 5
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 ...
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 Front Royal Entrance Shenandoah National Park ...
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
$59 nightly
The price is $66 total per night from Jul 30 to Jul 31
$66 total
Jul 30 - Jul 31
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
$70 nightly
The price is $77 total per night from Jul 23 to Jul 24
$77 total
Jul 23 - Jul 24
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 Jul 26 to Jul 27
$159 total
Jul 26 - Jul 27
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! (442 reviews)
"Historic, charming, relaxing."
Reviewed on Jul 14, 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 $104 total per night from Aug 11 to Aug 12
$104 total
Aug 11 - Aug 12
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
$101 nightly
The price is $113 total per night from Aug 9 to Aug 10
$113 total
Aug 9 - Aug 10
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
$93 nightly
The price is $103 total per night from Jul 28 to Jul 29
$103 total
Jul 28 - Jul 29
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)
"Prices are getting too high for this location"
Reviewed on Jul 20, 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
$130 nightly
The price is $145 total per night from Jul 29 to Jul 30
$145 total
Jul 29 - Jul 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 ...
9.2/10 Wonderful! (1,002 reviews)
"Wonderful hotel. Nice and clean!!!"
Reviewed on Jul 21, 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 - 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
$43
$132 total
found 1 day ago
Compact
Hanover, District of Columbia, USA
$43
$132 total
found 1 day ago
Standard SUV
Baltimore, Maryland, USA
$45
$132 total
found 1 day ago
Midsize
Hanover, District of Columbia, USA
$46
$140 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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