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Winston

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Winston Flights as Low as $143

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Cheap Flights to Winston

Fall in love at first flight with your vacation to Winston 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 Winston on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Winston

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winston 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 RBG airport.

What is the cheapest month to fly to Winston?

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 Winston are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winston?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 13 to choose from for your flight to Winston.

What airport is best to fly into Winston?

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

How much are flights to Winston?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winston on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $143, 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 Winston?

The trick to saving a stack of cash on your flight to Winston? 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 $143 right now, why wait?

Winston Flight Information
Destination airport
Rogue Valley Intl.
Destination airport IATA code
MFR
Roundtrip price
$295

Last Minute Hotel Deals in Winston

Safari Inn

Safari Inn

2 out of 5
101 NE Main Street, Winston, OR
Stay at this motel in Winston. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.6/10 Good! (354 reviews)
"A quiet little place . Just right down the street from wildlife Safari ."

Reviewed on Jun 30, 2025

Safari Inn
Family-friendly Winston Vacation Rental w/ Deck!

Family-friendly Winston Vacation Rental w/ Deck!

3 out of 5
Winston
Stay at this 3-star family-friendly cottage in Winston. Enjoy free parking and air conditioning. Popular attractions South Umpqua River and Wildlife Safari are ...
"This house was beautiful, affordable, and very spacious! It had every single amenity you would need and many extras too! The host was extremely attentive and informative with check on and out process and also making sure we could contact her at any time if needed. I definitely recommend this house ..."

Reviewed on Apr 5, 2024

Family-friendly Winston Vacation Rental w/ Deck!
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! (1,354 reviews)
"Beautiful river view. Close to old downtown."

Reviewed on Aug 1, 2025

Riverfront Inn Roseburg
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! (1,003 reviews)
"Took awhile for someone to come to the front desk to check us in. Rooms were clean and comfortable."

Reviewed on Jul 30, 2025

Sleep Inn & Suites Roseburg North Near Medical Center
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)
"Friendly service"

Reviewed on Aug 2, 2025

Super 8 by Wyndham Roseburg
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)
"The hotel is beautiful and well kept. The rooms are clean and pretty. The staff are wonderful and quick. The breakfast maybe could use a facelift. The food is ok but tsome of it doesnt tast that great. The omlettes are like rubbery and no flavor and the sausage isnt very good."

Reviewed on Aug 2, 2025

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 WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (1,001 reviews)
"Great overnight stay for road trip"

Reviewed on Jul 31, 2025

Best Western Garden Villa Inn
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. ...
7.2/10 Good! (1,003 reviews)
"Bed was ok."

Reviewed on Jul 28, 2025

Motel 6 Roseburg, OR
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.