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Winchester

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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! (1,404 reviews)
"Don’t let the outside fool you. It’s clean & well appointed. Be sure to get a room on the backside. Less road noise."

Reviewed on Sep 22, 2025

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Riverfront Inn Roseburg
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! (1,019 reviews)
"We found it satisfactory in all the basics."

Reviewed on Sep 21, 2025

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Super 8 by Wyndham 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! (1,015 reviews)
"It was clean enough for a one night stay, staff was friendly, beds were clean."

Reviewed on Sep 23, 2025

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Motel 6 Sutherlin, OR
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! (1,012 reviews)
"It was a really nice room and right off the highway. It’s in a nice town with lots of dining. We chose it for it’s direct route to Crater Lake NP My 4 star is for location: it is sandwiched directly between an interstate and a highway so the road noise makes it difficult for a quiet sleep"

Reviewed on Sep 20, 2025

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Sleep Inn & Suites Roseburg North Near Medical Center
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! (1,017 reviews)
No issues
"Not bad for a motel 6. No issues."

Reviewed on Sep 20, 2025

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Motel 6 Roseburg, 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)
"I stayed in a suite on the ground floor. Very nice room with a beautiful terrace overlooking the River. I especially want to thank Jessica at the front desk for going the extra mile."

Reviewed on Sep 24, 2025

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Holiday Inn Express Roseburg by IHG
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 ...
7.8/10 Good! (1,012 reviews)
Clean place but sort of uncomfortable
"Noisy a/c with confusing panel buttons. Spongy pillows were not very conforming and mattress was very firm, which was uncomfortable for us."

Reviewed on Sep 21, 2025

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Best Western Garden Villa Inn
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 ...
5.4/10 (92 reviews)
"We were welcomed with kind staff and ease of check in. The room was clean. We appreciated the mini fridge for keeping our drinks cold, since we had high temps the weekend we stayed. No microwave in the room we were in, but we were not in the room for dinners."

Reviewed on Aug 27, 2025

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Rosewood Inn and Suites
See all 112 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.