Cheap Flights to Winchester from $128
Wander Wisely with exceptional service, 24/7 supportOpens in a new window
Feel at ease with free flight cancellations within 24 hours of booking
Change your flight without a fee on select flights
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 $128 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 | May 23 to May 24 | $231 |
| SAN | Lexington | May 19 to May 23 | $237 |
| IAH | Lexington | March 20 to March 30 | $269 |
| EWR | Lexington | May 5 to May 12 | $269 |
| SEA | Lexington | May 19 to May 28 | $309 |
| LAX | Lexington | April 20 to April 28 | $315 |
| PHL | Lexington | April 6 to April 8 | $369 |
| DFW | Lexington | April 24 to April 25 | $435 |
| SOF | Lexington | May 5 to July 31 | $771 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $189 |
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
Bathroom door didn’t close.
Reviewed on Feb 6, 2026
Red Roof Inn Winchester - Lexington East
The room was clean but there was a strong cleaning chemical smell inside that bothered me as I am sensitive to strong scent. They only give 1 small bottle of shampoo and no conditioner. No breakfast either. It’s all good as we only needed one night stay and for that price it’s all good.
Reviewed on Feb 21, 2026
Best Western Winchester Hotel
The room was really clean. The remote and TV system sucks. It’s ridiculously hard and the remotes are awful. There was no freezer in the fridge, but the people out the front desk were nice enough to keep my ice packs cold in their freezer. Unfortunately my smoke free room was not smoke-free and when ...
Reviewed on Mar 4, 2026
Luxury Hotels in Winchester
Best Western Winchester Hotel
The room was really clean. The remote and TV system sucks. It’s ridiculously hard and the remotes are awful. There was no freezer in the fridge, but the people out the front desk were nice enough to keep my ice packs cold in their freezer. Unfortunately my smoke free room was not smoke-free and when ...
Reviewed on Mar 4, 2026
Family Friendly Hotels in Winchester
Baymont by Wyndham Winchester
Bathroom door didn ’t close.
Reviewed on Feb 6, 2026
Hampton Inn Winchester
Room was clean and modern.
Reviewed on Mar 1, 2026
Best Western Winchester Hotel
The room was really clean. The remote and TV system sucks. It’s ridiculously hard and the remotes are awful. There was no freezer in the fridge, but the people out the front desk were nice enough to keep my ice packs cold in their freezer. Unfortunately my smoke free room was not smoke-free and when ...
Reviewed on Mar 4, 2026
Red Roof Inn Winchester - Lexington East
The room was clean but there was a strong cleaning chemical smell inside that bothered me as I am sensitive to strong scent. They only give 1 small bottle of shampoo and no conditioner. No breakfast either. It’s all good as we only needed one night stay and for that price it’s all good.
Reviewed on Feb 21, 2026
Best Winchester Flight and Hotel Packages
Winchester flight + hotel packages - economy flights
Need a Car For After Your Flight?
Economy
Compact
Midsize
SUV
Plane Tickets To Winchester
Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Winchester. Browse through our inventory to explore a wide range of cheap flights to Winchester to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Winchester as you anxiously await to exit the plane and explore what Winchester has to offer. Considering all the amazing local food and culture in Winchester, we won't hold this against you.
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!
Explore More Ways to Travel with Travelocity
- Hotels near Kentucky River
- Hotels near Lykins Park
- Hotels near Boone Station State Historic Site
- Hotels near Raven Run Nature Sanctuary
- Liberty Area Hotels
- Hotels near Claiborne Farm
- Hotels near The Thoroughbred Center
- Hotels near Jacobson Park
- Hotels near Grimes Mill Winery
- Hotels near Southwind Golf Course
- Hotels near The Cane Ridge Meeting House
- Hotels near Lexington Ice Center
- Hotels near Clark Regional Medical Center
- 3 Star Hotels in Paris
- Farmstay in Paris
- Apartments in Paris
- B&B in Paris
- Cabins in Paris
- Castles in Paris
- Cottages in Paris
- Extended Stay Hotels in Paris
- Cheap Hotels in Paris
- Convention Center Hotels in Paris
- Kid Friendly Hotels in Paris
- Hotels with Pools in Paris
- Romantic Getaways & Hotels in Paris
- Paris Hotels
- Motels in Paris
- Hotels near Talon Winery
- Hotels near Shriners Hospitals for Children
- Lexington Hotels
- Farmstay in Mount Sterling
- Apartments in Mount Sterling
- B&B in Mount Sterling
- Cabins in Mount Sterling
- Chalets in Mount Sterling
- Condos in Mount Sterling
- Cottages in Mount Sterling
- Extended Stay Hotels in Mount Sterling
- Cheap Hotels in Mount Sterling
- Historic Hotels in Mount Sterling
- Hotels with Free Parking in Mount Sterling
- Hotels with Hot Tubs in Mount Sterling
- Hotels with an Indoor Pool in Mount Sterling
- Pet Friendly Hotels in Mount Sterling
- Red Roof Inn Hotels in Mount Sterling
- Mount Sterling Hotels
- Motels in Mount Sterling
- Vacation Homes in Mount Sterling
- Rv Parks in Mount Sterling
- Town Houses in Mount Sterling
- Villas in Mount Sterling
- Hotels near Castlewood Park
- Hotels near Duncan Tavern Historic Center
- Hotels near Fort Boonesborough State Park
- Flights to Northern Kentucky
- Flights to Richmond
- Flights to Morehead
- Flights to Georgetown
- Flights to Nicholasville
- Flights to Frankfort
- Flights to Danville
- Flights from Blue Grass
- Flights to Stanford
- Flights to Slade
- Flights to Lancaster
- Flights to Maysville
- Flights to Lawrenceburg
- Flights to Williamstown
- Flights to Symbol
- Flights to Dry Ridge
- Flights to Sadieville
- Flights to Berea
- Flights to Kentucky
- Flights to Versailles
- Flights to Fleming County
- Flights to Lexington
- Flights to Mount Sterling
- Flights from Baltimore to Mount Sterling
- Flights from Columbus to Mount Sterling
- Flights from Denver to Mount Sterling
- Flights from Salt Lake City to Mount Sterling
- Flights to Beattyville
- Flights to Shelbyville
- Flights to West Liberty
- Flights to East Bernstadt
- Flights to Harrodsburg
- Flights to Junction City
- Flights to Olive Hill
- Flights to Carlisle