Cheap Flights to Winchester from $122
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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 $189 and $122 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| DEN | Lexington | March 24 to March 30 | $239 |
| IAH | Lexington | February 14 to February 21 | $269 |
| EWR | Lexington | February 10 to February 18 | $269 |
| SAN | Lexington | March 25 to March 30 | $276 |
| LAX | Lexington | March 12 to April 1 | $305 |
| SEA | Lexington | April 17 to April 21 | $309 |
| TTN | Lexington | April 11 to April 14 | $372 |
| DFW | Lexington | February 19 to February 24 | $376 |
| FCO | Lexington | April 1 to April 12 | $673 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $189 |
Number of Airlines Serving | |
Airlines Serving | American Airlines |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Winchester Accommodation Deals
Baymont by Wyndham Winchester
Great stay and the bed was extremely comfortable
Reviewed on Jan 11, 2026
Red Roof Inn Winchester - Lexington East
Very clean. Traveled with 2 small dogs, so no carpeting in our room was perfect. The staff was very friendly and accommodating. The young lady at the desk found a hair dryer for me. I will definitely be staying each time I visit.
Reviewed on Nov 1, 2025
Best Western Winchester Hotel
Room was fine. Staff was nice. Didn’t eat breakfast because we had a brunch to go to.
Reviewed on Dec 14, 2025
Luxury Hotels in Winchester
Best Western Winchester Hotel
Room was fine. Staff was nice. Didn’t eat breakfast because we had a brunch to go to.
Reviewed on Dec 14, 2025
Family Friendly Hotels in Winchester
Baymont by Wyndham Winchester
Great stay and the bed was extremely comfortable
Reviewed on Jan 11, 2026
Hampton Inn Winchester
Overall the hotel was good - very friendly staff, safe area, clean and presentable. I was quite surprised and astonished by the $75 pet fee - it is outrageous for adding a dog to add $75 to a $150 room. This also was not clearly presented during the booking process.
Reviewed on Jan 4, 2026
Best Western Winchester Hotel
Room was fine. Staff was nice. Didn’t eat breakfast because we had a brunch to go to.
Reviewed on Dec 14, 2025
Red Roof Inn Winchester - Lexington East
Very clean. Traveled with 2 small dogs, so no carpeting in our room was perfect. The staff was very friendly and accommodating. The young lady at the desk found a hair dryer for me. I will definitely be staying each time I visit.
Reviewed on Nov 1, 2025
Best Winchester Flight and Hotel Packages
Winchester flight + hotel packages - economy flights
Need a Car For After Your Flight?
Compact SUV
$19
Standard
$38
Midsize
$39
Fullsize
$40
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!
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