Cheap Flights to Winchester from $29
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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 $58 and $29 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.
$58 Roundtrip, found 4 hours ago
$58
Roundtrip
found 4 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Baltimore | July 14 to July 21 | $58 |
| ATL | Chantilly | July 14 to July 21 | $58 |
| CLT | Baltimore | June 23 to June 24 | $80 |
| FLL | Chantilly | July 15 to July 21 | $86 |
| DFW | Baltimore | July 15 to July 28 | $100 |
| DFW | Chantilly | August 13 to August 18 | $108 |
| BOS | Washington | August 5 to August 12 | $117 |
| BOS | Chantilly | June 3 to June 9 | $117 |
| ATL | Washington | August 4 to August 8 | $189 |
| FLL | Washington | June 16 to June 27 | $197 |
| LAX | Chantilly | August 11 to August 18 | $210 |
| DFW | Washington | August 5 to August 9 | $210 |
| SFO | Chantilly | August 13 to August 16 | $244 |
| SFO | Baltimore | August 16 to August 20 | $254 |
| SFO | Washington | August 1 to August 9 | $254 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | Washington | May 16 to May 17 | $246 |
| FLL | Baltimore | May 16 to May 31 | $246 |
| ATL | Chantilly | May 16 to May 24 | $282 |
| FLL | Chantilly | May 16 to May 24 | $286 |
| BOS | Baltimore | May 15 to May 23 | $301 |
| DFW | Chantilly | May 16 to June 8 | $301 |
| BOS | Chantilly | May 17 to May 19 | $330 |
| DFW | Baltimore | May 16 to May 18 | $368 |
| BOS | Washington | May 17 to May 20 | $407 |
| LAX | Chantilly | May 17 to May 20 | $454 |
| LAX | Baltimore | May 17 to May 20 | $454 |
| SFO | Washington | May 16 to May 18 | $500 |
| LAX | Washington | May 16 to May 19 | $526 |
| SFO | Baltimore | May 16 to May 18 | $572 |
| ATL | Washington | May 16 to May 18 | $635 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $58 |
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 May 14 to May 15
$77 total
May 14 - May 15
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. ...
8/10 Very Good! (1,006 reviews)
We was pretty shocked when I got into the room. First thing I did was went into the bathroom, someone had used it without flushing,let that slide. Went to get ready for bed, there was pubic hair in the sheets,the blankets had cigarette burns and it smelled of old cigarettes. Yes I probably should've ...
Reviewed on May 7, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$71 nightly
The price is $77 total per night from May 17 to May 18
$77 total
May 17 - May 18
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! (1,065 reviews)
Clean ,comfortable, and a safe place to spend the night.
Reviewed on May 13, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
$84 nightly
The price is $93 total per night from May 18 to May 19
$93 total
May 18 - May 19
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! (553 reviews)
The room was very clean and comfortable. We enjoyed our stay and enjoyed being able to pull up to the room and unload with no steps or elevator to get on.
Reviewed on May 12, 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 May 14 to May 15
$77 total
May 14 - May 15
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. ...
8/10 Very Good! (1,006 reviews)
We was pretty shocked when I got into the room. First thing I did was went into the bathroom, someone had used it without flushing,let that slide. Went to get ready for bed, there was pubic hair in the sheets,the blankets had cigarette burns and it smelled of old cigarettes. Yes I probably should've ...
Reviewed on May 7, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$71 nightly
The price is $77 total per night from May 17 to May 18
$77 total
May 17 - May 18
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! (1,065 reviews)
Clean ,comfortable, and a safe place to spend the night.
Reviewed on May 13, 2026
Wayside Inn
7783 Main St Middletown VA
$144 nightly
The price is $159 total per night from May 17 to May 18
$159 total
May 17 - May 18
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! (430 reviews)
Cozy and quaint. Felt like being in a home filled with lots of history! The people were very friendly in the restaurant and bar. Would definitely stay again.
Reviewed on May 10, 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 $102 total per night from Jun 7 to Jun 8
$102 total
Jun 7 - Jun 8
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 hotel was very good but the breakfast was lacking food. Especially the milk was terrible.
Reviewed on May 9, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$113 nightly
The price is $126 total per night from May 24 to May 25
$126 total
May 24 - May 25
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! (1,000 reviews)
The view of the mountains from my room was majestic, but the window to view it left me wanting.
Reviewed on May 7, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$88 nightly
The price is $96 total per night from May 25 to May 26
$96 total
May 25 - May 26
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)
Great breakfast. Very clean. Parking was safe and easy. Staff was excellent!
Reviewed on May 5, 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 May 25 to May 26
$136 total
May 25 - May 26
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! (1,008 reviews)
Expedia over booked the hotel and when I got to my destination I didn’t have a hotel room to stay in. The hotel cancelled my reservation because Expedia over booked them.
Reviewed on May 10, 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.
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
$40
$80 total
found 2 days ago
Compact
Hanover, District of Columbia, USA
$40
$80 total
found 2 days ago
Midsize
Hanover, District of Columbia, USA
$44
$88 total
found 2 days ago
Special
Hanover, District of Columbia, USA
$47
$94 total
found 2 days 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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