Search Cheap Flights to
Winchester

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Cheap Flights to Winchester

Fall in love at first flight with your vacation to Winchester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Winchester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Winchester, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Winchester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winchester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the EUG airport.

What is the cheapest month to fly to Winchester?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Winchester are in , but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winchester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find  to choose from for your flight to Winchester.

What airport is best to fly into Winchester?

When you’re planning your trip to Winchester, convenience is the name of the game. Luckily, Winchester Southwest Oregon Regional Airport is nearby so you can deplane and get going on checking off everything on your Winchester must-do list.

How much are flights to Winchester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winchester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as , you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Winchester?

The trick to saving a stack of cash on your flight to Winchester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as  right now, why wait?

Winchester Flight Information
Destination airport
Winchester
Destination airport IATA code
EUG

Last Minute Hotel Deals in Winchester

Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave, Roseburg, OR
Stay at this motel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (1,402 reviews)
"It is an older hotel. But was very clean (except the balcony). The office staff was fantastic, extra kudos to the night shift. Sorry didn't get her name. Bed was very comfortable and it was very relaxing sitting on the balcony after a long drive. I gave it overall 5 stars, can't beat the price."

Reviewed on Oct 3, 2025

Get rates
Riverfront Inn Roseburg
Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

2 out of 5
1400 Hospitality Way, Sutherlin, OR
Stay at this motel in Sutherlin. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (1,001 reviews)
"Very basic place as indicated by the price. No toiletries besides a couple of small bar soap s. Just needed a place to crash for a few hours so it was fine."

Reviewed on Oct 2, 2025

Get rates
Motel 6 Sutherlin, OR
Holiday Inn Express Roseburg by IHG

Holiday Inn Express Roseburg by IHG

2.5 out of 5
375 Harvard Blvd, Roseburg, OR
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,001 reviews)
"Carpet was extremely dirty, rooms are very outdated, behind the night stand was a little trash, but staff was friendly and it was safe, close to freeway and the parking was very convenient. View to the lake was pleasant. Beds were very comfortable and clean at least and in the bathroom even though ..."

Reviewed on Oct 4, 2025

Get rates
Holiday Inn Express Roseburg by IHG
Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg

2.5 out of 5
3200 Nw Aviation Dr I-5 Exit # 127, Roseburg, OR
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (1,003 reviews)
"I always say the staff will make a break a property. This staff made the property."

Reviewed on Oct 4, 2025

Get rates
Super 8 by Wyndham Roseburg
Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

2 out of 5
3100 Nw Aviation Dr, Roseburg, OR
Stay at this motel in Roseburg. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (1,006 reviews)
"For the price it was a great value"

Reviewed on Oct 3, 2025

Get rates
Motel 6 Roseburg, OR
Best Western Garden Villa Inn

Best Western Garden Villa Inn

2.5 out of 5
760 NW Garden Valley Boulevard, Roseburg, OR
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,002 reviews)
"The room was clean and comfortable. Good value"

Reviewed on Oct 4, 2025

Get rates
Best Western Garden Villa Inn
Sleep Inn & Suites Roseburg North Near Medical Center

Sleep Inn & Suites Roseburg North Near Medical Center

2.5 out of 5
2855 NW Edenbower Blvd, Roseburg, OR
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (1,001 reviews)
"Ty"

Reviewed on Sep 30, 2025

Get rates
Sleep Inn & Suites Roseburg North Near Medical Center
Rosewood Inn and Suites

Rosewood Inn and Suites

2.5 out of 5
790 NW Garden Valley Blvd, Roseburg, OR
Stay at this motel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Umpqua ...
5.6/10 (96 reviews)
"spacious room"

Reviewed on Sep 29, 2025

Get rates
Rosewood Inn and Suites
See all 114 properties in 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.