Cheap Flights to Winchester from $150
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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 $271 and $150 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 | July 1 to July 4 | $296 |
| EWR | Lexington | August 4 to August 18 | $310 |
| IAH | Lexington | July 4 to July 11 | $316 |
| LAX | Lexington | August 11 to August 15 | $335 |
| SEA | Lexington | August 26 to September 16 | $349 |
| PHL | Lexington | July 8 to July 14 | $423 |
| SAN | Lexington | July 1 to July 22 | $423 |
| DFW | Lexington | July 1 to July 6 | $456 |
| FCO | Lexington | June 14 to June 18 | $1,071 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $271 |
Number of Airlines Serving | |
Airlines Serving | Delta, United |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Winchester Accommodation Deals
Baymont by Wyndham Winchester
"Shower dirty hairs all over the walls"
Reviewed on Jun 1, 2026
Red Roof Inn Winchester - Lexington East
"Worth the $ if your not looking to spend a fortune. Just a nice clean affordable place to sleep and get down the road."
Reviewed on May 7, 2026
Best Western Winchester Hotel
"We just booked a weekend stay with our 3 grandkids. The staff was friendly and helpful. The facilities were clean. The breakfast was fine. I am disappointed that the pool was closed for painting the weekend we booked. No one told us!! We had 3 grandchildren with us and that is why we booked the BW, ..."
Reviewed on May 31, 2026
Luxury Hotels in Winchester
Best Western Winchester Hotel
"We just booked a weekend stay with our 3 grandkids. The staff was friendly and helpful. The facilities were clean. The breakfast was fine. I am disappointed that the pool was closed for painting the weekend we booked. No one told us!! We had 3 grandchildren with us and that is why we booked the BW, ..."
Reviewed on May 31, 2026
Family Friendly Hotels in Winchester
Baymont by Wyndham Winchester
"Shower dirty hairs all over the walls"
Reviewed on Jun 1, 2026
Hampton Inn Winchester
"Room was nice, hotel is quiet, and breakfast was clean and organized."
Reviewed on May 29, 2026
Best Western Winchester Hotel
"We just booked a weekend stay with our 3 grandkids. The staff was friendly and helpful. The facilities were clean. The breakfast was fine. I am disappointed that the pool was closed for painting the weekend we booked. No one told us!! We had 3 grandchildren with us and that is why we booked the BW, ..."
Reviewed on May 31, 2026
Red Roof Inn Winchester - Lexington East
"Worth the $ if your not looking to spend a fortune. Just a nice clean affordable place to sleep and get down the road."
Reviewed on May 7, 2026
Need a Car For After Your Flight?
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Plane Tickets To Winchester
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