Cheap flights from Winchester

Many airlines offer flexible change policies

Earn BONUS+ rewardsOpens in a new window on top of your airline points

Enjoy exclusive promotions on the ebookers app!

Winchester Flight Information
Origin airport IATA code
CHA

Sourcing the best flights from Winchester on ebookers

If you’re seeking a flight from Winchester, you can swiftly and easily find exactly what you’re looking for using ebookers. Our easy-to-use tool will let you select the destination and ideal travel dates to immediately see which routes and airlines are available. Have a preferred airline in mind for the trip? You can filter your ebookers search to see if they have flights from CHA. For more bespoke options, you can also set your search for multiple destinations and flights that are refundable, so you can have the most relevant information in moments.

Getting the best deal on a cheap flight from CHA

There are a few golden rules for keeping costs low when booking flights from Winchester. The first thing to think about is being flexible on your travel dates. It can help to shift your departure by a day, or even a few hours, as prices can vary by significant amounts. Use ebookers to compare and contrast your options ahead of time, and you can make a savvy decision. Want more savings? If book the hotel at your chosen destination through ebookers while also arranging your flight from Winchester, you can get a discount of up to 15% off the total price. For help on which pad to pick, you can make use of our snappy hotel descriptions, which are accompanied by useful photos.

Getting things going at your destination

With ebookers, you don’t just have access to the latest, constantly updated information on flights from CHA. You can also get inspiration on the most interesting things to get up to when you’re there. Just check out our Things to Do tool and you’ll soon be drawing up an exciting itinerary. And if you’re keen to take in as much of the wider area as possible, you could also look into the best car hire deals and have your very own set of wheels waiting, so you can roam to your heart’s content.

Featured Hotels near Winchester

Beautiful Lake Views at Twin Creeks!

Beautiful Lake Views at Twin Creeks!

Winchester TN
During your stay at this holiday home, you're just a quick walk from Tims Ford State Park. Enjoy features like an outdoor pool, laundry facilities and an arcade/games room. The holiday home offers free WiFi and a kitchen.
9.8/10 Exceptional! (56 reviews)
We had a Great Week!
The house was good. I am taking off a star because the queen bed in the one bedroom was atrocious. There was a mattress sitting on slats that were too far apart and not nearly supportive enough. We could not use that bed. I did not address it with the owner while we were there because I was on vacation ...

Reviewed on 21 Jul 2025

Opens in a new windowBeautiful Lake Views at Twin Creeks!
The Sewanee Inn

The Sewanee Inn

4 out of 5
1235 University Ave Sewanee TN
The price is €217 per night from 16 Dec to 17 Dec
€217
16 Dec - 17 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at The Sewanee Inn. During your stay, you're just a quick walk from University of the South. Free WiFi in public areas, a restaurant and a golf course are available.
9.6/10 Exceptional! (391 reviews)
Great Hotel!! Super duper clean. The cleanest I ever seen Only recommendation is to add a gift shop that has snacks and toiletries. Also need to put a microwave somewhere that’s accessible. Great stay

Reviewed on 2 Dec 2025

Opens in a new windowThe Sewanee Inn
Best Western Inn

Best Western Inn

2.5 out of 5
1602 Dinah Shore Boulevard Winchester TN
The price is €98 per night from 8 Jan to 9 Jan
€98
8 Jan - 9 Jan 2026
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Best Western Inn. During your stay, you'll be within walking distance of County Plaza Shopping Center. Enjoy features like free breakfast, free WiFi in public areas and free self-parking.
8.6/10 Excellent! (659 reviews)
Pleasant stay, friendly check in

Reviewed on 9 Dec 2025

Opens in a new windowBest Western Inn
Save an average of 15% on thousands of hotels when you're signed in
Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

2 out of 5
201 Expressway Dr Manchester TN
The price is €63 per night from 17 Dec to 18 Dec
€63
17 Dec - 18 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Microtel Inn & Suites by Wyndham Manchester. During your stay, you'll be within walking distance of May Prairie Designated State Natural Area. Features include free breakfast, free WiFi in public areas and free self-parking.
8.6/10 Excellent! (993 reviews)
Clean room easy access and the staff was friendly.

Reviewed on 8 Dec 2025

Opens in a new windowMicrotel Inn & Suites by Wyndham Manchester
The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

3 out of 5
844 W Main Street Monteagle TN
The price is €48 per night from 4 Jan to 5 Jan
€48
4 Jan - 5 Jan 2026
includes taxes & fees
Our customers tell us they can't get enough of The Smokehouse Lodge and Cabins's great location. During your stay, you'll be within walking distance of Monteagle Sunday School Assembly. You'll find features such as free WiFi in public areas and free self-parking, plus an outdoor pool.
8.4/10 Very Good! (1,141 reviews)
The room was spotless. It was the perfect atmosphere before a day on the trails at Coalmont. ONLY suggestion Id have is put a fluffy comforter on the bed. Thank you! Ps. We loved it.

Reviewed on 9 Dec 2025

Opens in a new windowThe Smokehouse Lodge and Cabins
Spark by Hilton Kimball

Spark by Hilton Kimball

2.5 out of 5
205 Kimball Crossing Dr Jasper TN
The price is €75 per night from 9 Jan to 10 Jan
€75
9 Jan - 10 Jan 2026
includes taxes & fees
Our customers tell us that they enjoy the free breakfast at Spark by Hilton Kimball. During your stay, you'll be within walking distance of Kimball Park. You'll find features such as free WiFi in public areas and free self-parking, plus an outdoor pool.
8.2/10 Very Good! (1,001 reviews)
The room was clean and comfortable

Reviewed on 5 Dec 2025

Opens in a new windowSpark by Hilton Kimball
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.

Fare, taxes & fees: Fares were found on ebookers.com and are updated daily. They include all taxes and fees, except baggage fees.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a £25.00 / 45.00 Euro service fee charged by ebookers, plus any airline fare and tax increase that may be applicable.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.