Cheap Flights to Winchester from $109
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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 $179 and $109 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply
DCA
Ronald Reagan Washington National
LEX
Blue Grass
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| IAH | Lexington | December 25 to January 12 | $249 |
| DEN | Lexington | March 6 to March 9 | $249 |
| EWR | Lexington | February 12 to February 17 | $249 |
| DFW | Lexington | February 19 to February 24 | $269 |
| SEA | Lexington | February 2 to February 17 | $289 |
| LAX | Lexington | January 1 to January 18 | $289 |
| TTN | Lexington | February 14 to February 17 | $366 |
| SAN | Lexington | January 23 to February 18 | $381 |
| FCO | Lexington | February 25 to March 31 | $715 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| DEN | Lexington | December 12 to December 21 | $349 |
| IAH | Lexington | December 12 to January 2 | $406 |
| EWR | Lexington | December 14 to December 21 | $415 |
| DFW | Lexington | December 12 to December 31 | $523 |
| LAX | Lexington | December 13 to December 23 | $551 |
| SEA | Lexington | December 12 to December 14 | $558 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $179 |
Number of Airlines Serving | |
Airlines Serving | Delta |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Winchester Accommodation Deals
Baymont by Wyndham Winchester
960 Interstate Dr Winchester KY
$71 nightly
The price is $79 total per night from Dec 7 to Dec 8
$79 total
Dec 7 - Dec 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 clean rooms in our reviews. ...
7/10 Good! (770 reviews)
The person who checked us in was very friendly and helpful. We often stay here as we travel to visit family and the rooms are spacious and very clean and comfortable. Breakfast in the morning is simple and the area is always clean and well stocked. This is the perfect, inexpensive stop for a good ...
Reviewed on Nov 30, 2025
Red Roof Inn Winchester - Lexington East
1100 Interstate Drive Winchester KY
$62 nightly
The price is $69 total per night from Dec 8 to Dec 9
$69 total
Dec 8 - Dec 9
Total with taxes and fees
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions The Holler and Lykins Park are located ...
6.4/10 (585 reviews)
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
1307 W Lexington Ave Winchester KY
$89 nightly
The price is $98 total per night from Dec 9 to Dec 10
$98 total
Dec 9 - Dec 10
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,000 reviews)
This is our 2nd time staying here. Convenient stop on our trip. Rooms are clean and well maintained. The night check in guy Jared was very friendly & helpful.
Reviewed on Nov 25, 2025
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
Best Western Winchester Hotel
1307 W Lexington Ave Winchester KY
$89 nightly
The price is $98 total per night from Dec 9 to Dec 10
$98 total
Dec 9 - Dec 10
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,000 reviews)
This is our 2nd time staying here. Convenient stop on our trip. Rooms are clean and well maintained. The night check in guy Jared was very friendly & helpful.
Reviewed on Nov 25, 2025
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
Baymont by Wyndham Winchester
960 Interstate Dr Winchester KY
$71 nightly
The price is $79 total per night from Dec 7 to Dec 8
$79 total
Dec 7 - Dec 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 clean rooms in our reviews. ...
7/10 Good! (770 reviews)
The person who checked us in was very friendly and helpful. We often stay here as we travel to visit family and the rooms are spacious and very clean and comfortable. Breakfast in the morning is simple and the area is always clean and well stocked. This is the perfect, inexpensive stop for a good ...
Reviewed on Nov 30, 2025
Hampton Inn Winchester
1025 Early Dr Winchester KY
$106 nightly
The price is $117 total per night from Dec 28 to Dec 29
$117 total
Dec 28 - Dec 29
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 helpful staff and the clean ...
9.2/10 Wonderful! (449 reviews)
Clean and quiet stay.
Reviewed on Nov 27, 2025
Best Western Winchester Hotel
1307 W Lexington Ave Winchester KY
$89 nightly
The price is $98 total per night from Dec 9 to Dec 10
$98 total
Dec 9 - Dec 10
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,000 reviews)
This is our 2nd time staying here. Convenient stop on our trip. Rooms are clean and well maintained. The night check in guy Jared was very friendly & helpful.
Reviewed on Nov 25, 2025
Save an average of 15% on thousands of hotels when you're signed in
Red Roof Inn Winchester - Lexington East
1100 Interstate Drive Winchester KY
$62 nightly
The price is $69 total per night from Dec 8 to Dec 9
$69 total
Dec 8 - Dec 9
Total with taxes and fees
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions The Holler and Lykins Park are located ...
6.4/10 (585 reviews)
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
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.
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Price found within the past 48 hours. Click for updated prices.
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Plane Tickets To Winchester
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