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! (1,426 reviews)
Nice hotel/motel
"Outside looks kind of old but the rooms are great."

Reviewed on Oct 18, 2025

Get rates
Riverfront Inn 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! (1,004 reviews)
"Watching the planes take off and land from the airport next door love watching the planes taking off from there"

Reviewed on Oct 15, 2025

Get rates
Motel 6 Roseburg, OR
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! (1,010 reviews)
"It was okay for a night -- not much nearby. The AC didn't seem to be working properly in our room / was a bit inconsistent, but didn't seem to be worth it to say anything!"

Reviewed on Oct 14, 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! (1,005 reviews)
"Hotel is in a very convenient area right off the highway. Downtown Roseburg is a short walk away. Room was big and well appointed. I gave an average rating due to the fact the room could use some new carpet. Room was very clean otherwise. Breakfast was very good with plenty of options!"

Reviewed on Oct 15, 2025

Get rates
Holiday Inn Express Roseburg by IHG
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 (104 reviews)
"As I said above"

Reviewed on Oct 13, 2025

Get rates
Rosewood Inn and Suites
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! (1,010 reviews)
"Good location. Breakfast not great."

Reviewed on Oct 8, 2025

Get rates
Super 8 by Wyndham Roseburg
Comfort Inn Roseburg

Comfort Inn Roseburg

2.5 out of 5
1539 NW Mullholland Drive, Roseburg, OR
Book a stay at this golf hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.2/10 Very Good! (1,010 reviews)
"The room was clean and spacious. The pool and hot tub were nice."

Reviewed on Oct 13, 2025

Get rates
Comfort Inn Roseburg
Best Western Plus Hartford Lodge

Best Western Plus Hartford Lodge

2.5 out of 5
150 Myrtle St, Sutherlin, OR
Book a stay at this business-friendly hotel in Sutherlin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,007 reviews)
"The only reason not a five star was that the disinfect smell in the rug, became over powering as the night progressed. We arrived late so did not have the energy to change room. Woke up with taste of soap or cleaning solution."

Reviewed on Oct 9, 2025

Get rates
Best Western Plus Hartford Lodge
See all 119 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.