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 $69 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.
IAD
Washington Dulles Intl.
$69 Roundtrip, just found
$69
Roundtrip
just found
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | September 26 to September 29 | $69 |
| ATL | Baltimore | October 10 to October 17 | $82 |
| CLT | Baltimore | October 1 to October 5 | $91 |
| BOS | Baltimore | October 26 to October 29 | $117 |
| FLL | Baltimore | September 30 to October 3 | $135 |
| DFW | Chantilly | October 27 to October 31 | $151 |
| CLT | Washington | October 17 to October 20 | $162 |
| CLT | Chantilly | September 24 to September 28 | $163 |
| BOS | Chantilly | November 12 to November 15 | $209 |
| FLL | Washington | September 23 to September 30 | $217 |
| DFW | Washington | October 6 to October 10 | $237 |
| LAX | Washington | November 5 to November 9 | $238 |
| LAX | Baltimore | November 4 to November 10 | $238 |
| SFO | Baltimore | October 1 to October 6 | $282 |
| FCO | Baltimore | November 18 to November 28 | $620 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | Chantilly | September 6 to September 9 | $201 |
| ATL | Chantilly | September 6 to September 7 | $258 |
| ATL | Baltimore | September 6 to September 12 | $292 |
| CLT | Chantilly | September 6 to September 7 | $299 |
| MCO | Chantilly | September 6 to September 8 | $311 |
| ATL | Washington | September 6 to September 9 | $314 |
| DFW | Chantilly | September 6 to September 9 | $324 |
| DFW | Washington | September 6 to September 10 | $324 |
| DFW | Baltimore | September 6 to September 9 | $357 |
| LAX | Washington | September 5 to September 9 | $440 |
| SFO | Washington | September 6 to September 10 | $446 |
| LAX | Baltimore | September 5 to September 10 | $465 |
| SFO | Baltimore | September 5 to September 12 | $557 |
| FCO | Chantilly | September 6 to September 19 | $772 |
| SFO | Chantilly | September 5 to September 12 | $829 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $69 |
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 16 to Sep 17
$82 total
Sep 16 - Sep 17
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)
"Clean room, friendly staff"
Reviewed on Aug 31, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $76 total per night from Sep 3 to Sep 4
$76 total
Sep 3 - Sep 4
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 Sep 6 to Sep 7
$91 total
Sep 6 - Sep 7
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! (576 reviews)
"The staff were nice, but the office was definitely not clean. So much so that we didn't want any breakfast from there. Parking is right off the main road, so be careful pulling in and out. Parking is right outside your room, which was nice. Traffic was quiet during the night, but loud during the ..."
Reviewed on Sep 1, 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
$72 nightly
The price is $82 total per night from Sep 16 to Sep 17
$82 total
Sep 16 - Sep 17
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)
"Clean room, friendly staff"
Reviewed on Aug 31, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $76 total per night from Sep 3 to Sep 4
$76 total
Sep 3 - Sep 4
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 Sep 6 to Sep 7
$159 total
Sep 6 - Sep 7
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)
"It was a very nice room with very comfortable bed. We misplaced the key and they were very helpful getting a replacement after hours. Fortunately, we found the lost key. Staff bwas very pleasant. Air conditioner was a little loud but effective. Did not prevent from sleeping. Would stay again."
Reviewed on Aug 29, 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
$101 nightly
The price is $112 total per night from Sep 27 to Sep 28
$112 total
Sep 27 - Sep 28
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! (1,001 reviews)
"Our stay here was wonderful! Very friendly and helpful staff. The cleanliness was excellent ! We will definitely stay here again."
Reviewed on Sep 2, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$123 nightly
The price is $136 total per night from Sep 9 to Sep 10
$136 total
Sep 9 - Sep 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
$80 nightly
The price is $89 total per night from Sep 8 to Sep 9
$89 total
Sep 8 - Sep 9
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)
"This place looks old on the exterior but it is clean and the rooms are remodeled. The beds were Comfortable with plenty of pillows and a roomy interior. A regular size small fridge and microwave were in our room. The pool is very clean and a decent size with plenty of chairs available. Breakfast ..."
Reviewed on Sep 1, 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 8 to Sep 9
$136 total
Sep 8 - Sep 9
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)
"The pool filter was broken and not open. When its this hot out the pool must be open. The breakfast was top notch though!"
Reviewed on Sep 1, 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.
Need a Car For After Your Flight?
Economy
Hanover, District of Columbia, USA
$25
$88 total
found 2 days ago
Compact SUV
BALTIMORE, USA
$26
$84 total
found 1 day ago
Midsize SUV
BALTIMORE, USA
$27
$88 total
found 1 day ago
Special
HANOVER, USA
$32
$101 total
found 1 day ago
Lowest prices found within the past 2 days. 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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