Cheap Flights to Winchester from $98

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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 $195 and $98 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
CMHLexingtonJune 23 to June 25$363
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
CMHLexingtonApril 27 to April 30$648
*Prices include taxes and fees

Winchester Flight Information

Traveling to
Winchester
Lowest Price
$195
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

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr, Winchester, KY
The price is $80 per night from Apr 28 to Apr 29
$80
per night
Apr 28 - Apr 29
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 rooms ...
6.8/10 (577 reviews)
"It was fairly clean but definitely a little dated. Can't beat it for the price. Front desk however was horrible. Not people friendly to say the least"

Reviewed on Apr 22, 2024

Baymont by Wyndham Winchester
Red Roof Inn Lexington - Winchester

Red Roof Inn Lexington - Winchester

2 out of 5
1100 Interstate Drive, Winchester, KY
The price is $71 per night from Apr 28 to Apr 29
$71
per night
Apr 28 - Apr 29
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Lykins Park and Community Park are located nearby. ...
6.2/10 (499 reviews)
"Outside of building was a little run down but the room was clean and updated and the staff was pleasant"

Reviewed on Apr 13, 2024

Red Roof Inn Lexington - Winchester
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave, Winchester, KY
The price is $90 per night from Apr 29 to Apr 30
$90
per night
Apr 29 - Apr 30
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! (806 reviews)
Good stay, excellent staff and breakfast
"We really enjoyed our stay. The room was clean and nice. Outside is dated but the rooms were good. Service was excellent, and the breakfast was great. Lots of choices and staff really kept everything stocked. My only issue was the beds were much too firm for me, personally, it was difficult to sleep. ..."

Reviewed on Apr 22, 2024

Best Western Winchester Hotel
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

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave, Winchester, KY
The price is $90 per night from Apr 29 to Apr 30
$90
per night
Apr 29 - Apr 30
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! (806 reviews)
Good stay, excellent staff and breakfast
"We really enjoyed our stay. The room was clean and nice. Outside is dated but the rooms were good. Service was excellent, and the breakfast was great. Lots of choices and staff really kept everything stocked. My only issue was the beds were much too firm for me, personally, it was difficult to sleep. ..."

Reviewed on Apr 22, 2024

Best Western Winchester Hotel
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
Great for families

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr, Winchester, KY
The price is $80 per night from Apr 28 to Apr 29
$80
per night
Apr 28 - Apr 29
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 rooms ...
6.8/10 (577 reviews)

Families like: Indoor pools, free breakfast for the whole family, laundry

Travelers say...
"It was fairly clean but definitely a little dated. Can't beat it for the price. Front desk however was horrible. Not people friendly to say the least"

Reviewed on Apr 22, 2024

Baymont by Wyndham Winchester
Hampton Inn Winchester
Great for families

Hampton Inn Winchester

2.5 out of 5
1025 Early Dr, Winchester, KY
The price is $150 per night from May 12 to May 13
$150
per night
May 12 - May 13
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 rooms ...
9.4/10 Exceptional! (355 reviews)

Families like: Outdoor pool, free breakfast for the whole family, laundry

Travelers say...
"Rooms were great and clean. The walls were thin. You could hear the neighbors talking."

Reviewed on Apr 16, 2024

Hampton Inn Winchester
Best Western Winchester Hotel
Great for families

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave, Winchester, KY
The price is $90 per night from Apr 29 to Apr 30
$90
per night
Apr 29 - Apr 30
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! (806 reviews)

Families like: Outdoor pool, extra beds/cribs, free breakfast for the whole family

Good stay, excellent staff and breakfast
"We really enjoyed our stay. The room was clean and nice. Outside is dated but the rooms were good. Service was excellent, and the breakfast was great. Lots of choices and staff really kept everything stocked. My only issue was the beds were much too firm for me, personally, it was difficult to sleep. ..."

Reviewed on Apr 22, 2024

Best Western Winchester Hotel
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Red Roof Inn Lexington - Winchester

Red Roof Inn Lexington - Winchester

2 out of 5
1100 Interstate Drive, Winchester, KY
The price is $71 per night from Apr 28 to Apr 29
$71
per night
Apr 28 - Apr 29
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Lykins Park and Community Park are located nearby. ...
6.2/10 (499 reviews)
"Outside of building was a little run down but the room was clean and updated and the staff was pleasant"

Reviewed on Apr 13, 2024

Red Roof Inn Lexington - Winchester
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.

Need a Car For After Your Flight?

Frequently asked questions

Which airlines fly to Winchester?
All set to make some new memories in Winchester? Delta Air Lines is one of the top carriers that service this destination.
What airport is best to fly into Winchester?
Traveling to and from Winchester is effortless, as it’s serviced by just one airport. You’ll find Blue Grass Airport around 25 mi from the city center.
Where to stay in Winchester
It’s time to stretch your wings and be inspired by Winchester, and the best place to start is with the search for a place to stay. Travelocity has 13 quality options just waiting to be booked.On the hunt for someplace to stay in Winchester? The 2nd Story Historic Downtown 2BR with Modern Amenities and the Hampton Inn Winchester are our recommended properties in this area.
Places to visit in Winchester
Educating yourself about the history of a region at Bluegrass Heritage Museum will surely make you feel more invested in the land and its inhabitants during your vacation. Want more options? Brush up on the difference between bogeys, birdies and backswings, with a round or two at Southwind Golf Course.
How to get through airport security fast when traveling to Winchester
Your trip to Winchester begins as soon as you’ve completed all the security checks. Here is a list of tips and pointers to ensure you get through quickly:

  • Airport security staff will request to see your boarding pass and travel ID at the checkpoint. Keep them in a convenient place, so they’re ready for inspection.
  • It’s useful to know that metal belt buckles can set off the body scanner’s alarms. If you have one on, you may be told to step back and remove it before moving on.
  • Electronics such as laptops, cameras and phones need to be put through the X-ray machine separately. Be sure to have them within easy reach.
  • When you approach the security checkpoint, you’ll be asked to place all creams, gels and liquids in a separate tray for inspection. Make sure they’re all in containers no larger than 3.4 ounces (100 milliliters) and sealed in a clear zip-lock bag.
  • Airport security staff will likely tell you to take off your shoes prior to entering the body scanner. Choose a pair that you can slip off easily. There’s nothing more annoying than having to do your laces up again and again.
  • Stash any multi-tools or other sharp items in your checked luggage. Security won’t allow these in carry-on baggage.

How to find cheap flights

What is the best day to buy a plane ticket?

Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you’re looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you’re browsing flight deals.

 

What are the cheapest days to fly?

Frequent travellers may already know this, earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.

 

How far in advance can you book a flight?

Here’s the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.

*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

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!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.