Cheap Flights to Winchester from $23
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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 $63 and $23 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$65 Roundtrip, found 2 days ago
$65
Roundtrip
found 2 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | December 1 to December 3 | $63 |
| FLL | Chantilly | November 4 to November 17 | $67 |
| ATL | Baltimore | December 1 to December 3 | $90 |
| CLT | Baltimore | October 29 to November 2 | $99 |
| FLL | Baltimore | November 3 to November 4 | $110 |
| BOS | Chantilly | November 4 to November 6 | $117 |
| BOS | Washington | November 6 to November 12 | $117 |
| BOS | Baltimore | November 7 to November 9 | $117 |
| ATL | Washington | December 9 to December 16 | $137 |
| FLL | Washington | November 10 to November 17 | $177 |
| DAL | Washington | October 17 to October 24 | $238 |
| LAX | Washington | November 3 to November 10 | $238 |
| SFO | Chantilly | October 19 to October 22 | $272 |
| SFO | Baltimore | November 2 to November 10 | $276 |
| FCO | Baltimore | November 15 to November 23 | $612 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | Chantilly | September 26 to October 20 | $162 |
| CLT | Baltimore | September 27 to September 28 | $292 |
| ATL | Chantilly | September 26 to September 28 | $334 |
| FLL | Baltimore | September 27 to October 3 | $345 |
| ATL | Baltimore | September 26 to October 3 | $379 |
| DFW | Chantilly | September 26 to September 27 | $421 |
| BOS | Washington | September 27 to October 7 | $445 |
| BOS | Baltimore | September 26 to October 3 | $446 |
| LAX | Chantilly | September 27 to October 10 | $459 |
| CLT | Chantilly | September 26 to September 28 | $484 |
| LAX | Baltimore | September 26 to October 13 | $539 |
| ATL | Washington | September 26 to October 3 | $620 |
| FCO | Chantilly | September 26 to October 9 | $991 |
| BOS | Chantilly | September 26 to October 3 | $1,020 |
| CLT | Washington | September 26 to September 27 | $1,136 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $63 |
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 29 to Sep 30
$82 total
Sep 29 - Sep 30
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)
"Good economical stay. Room was in good condition and comfortable. Appeared clean, but there were some roaches. Room was never cleaned while I stayed for 3 nights and only 2 sets of towels were provided. Felt safe and was pretty quiet. All 3 desk people I interacted with were very friendly and helpful. ..."
Reviewed on Sep 18, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $76 total per night from Sep 27 to Sep 28
$76 total
Sep 27 - Sep 28
Total with taxes and fees
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
Twi-Lite Inn
53 West 14th Street Front Royal VA
$82 nightly
The price is $91 total per night from Sep 27 to Sep 28
$91 total
Sep 27 - Sep 28
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! (580 reviews)
"Very cute little motel just a few minutes drive from the north entrance of the Skyline drive. The staff was extremely friendly. For the price, highly recommend."
Reviewed on Sep 23, 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
$72 nightly
The price is $82 total per night from Sep 29 to Sep 30
$82 total
Sep 29 - Sep 30
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)
"Good economical stay. Room was in good condition and comfortable. Appeared clean, but there were some roaches. Room was never cleaned while I stayed for 3 nights and only 2 sets of towels were provided. Felt safe and was pretty quiet. All 3 desk people I interacted with were very friendly and helpful. ..."
Reviewed on Sep 18, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $76 total per night from Sep 27 to Sep 28
$76 total
Sep 27 - Sep 28
Total with taxes and fees
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
Wayside Inn
7783 Main St Middletown VA
$94 nightly
The price is $104 total per night from Oct 15 to Oct 16
$104 total
Oct 15 - Oct 16
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! (448 reviews)
"We love staying at Wayside Inn. This is our third or fourth stay. The place is such a treasure! The food in the restaurant is good and the bar is fun. The only thing we noticed this time is that the bar closed at 9 p.m. on a Saturday night. We came in from dinner at 9:15 and planned to have a night ..."
Reviewed on Sep 22, 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 $105 total per night from Oct 25 to Oct 26
$105 total
Oct 25 - Oct 26
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)
"This property is very clean and comfortable. We enjoyed the indoor pool on a rainy afternoon. Our room was well equipped with a good desk & chair, comfortable bed, very clean bathroom, coffee maker, refrigerator, and plenty of space. I liked that the breakfast varied from day to day (we were there ..."
Reviewed on Sep 23, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$118 nightly
The price is $131 total per night from Oct 5 to Oct 6
$131 total
Oct 5 - Oct 6
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
$84 nightly
The price is $94 total per night from Oct 25 to Oct 26
$94 total
Oct 25 - Oct 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 ...
9.4/10 Exceptional! (1,002 reviews)
"It was our third time staying here—always such a great place to stay. The staff is the friendliest!"
Reviewed on Sep 23, 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
$137 nightly
The price is $153 total per night from Sep 27 to Sep 28
$153 total
Sep 27 - Sep 28
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 ...
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 - business class flights
Price found within the past 48 hours. Click for updated prices.
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See all available trips from Los Angeles to Winchester
View all tripsWinchester flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Special
HANOVER, USA
$23
$78 total
found 1 day ago
Economy
Baltimore, Maryland, USA
$28
$90 total
found 1 day ago
Standard
HANOVER, USA
$28
$91 total
found 1 day ago
Compact
HANOVER, USA
$29
$91 total
found 1 day ago
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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