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Winston

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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 , 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  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 , 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  right now, why wait?

Winston Flight Information
Destination airport
Winston
Destination airport IATA code
RBG

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! (363 reviews)
Loved it!
"A very nice basic room with everything you need and expect . The room was larger than most rooms Ive stayed in. Check in took 2 minutes! Quiet! And a great diner kitty-corner across the street"

Reviewed on Sep 10, 2025

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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 Wildlife Safari and South Umpqua River 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

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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! (1,388 reviews)
"Serviceable."

Reviewed on Sep 12, 2025

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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! (1,011 reviews)
"The staff was very nice and accommodating. Property was clean and safe."

Reviewed on Sep 5, 2025

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Motel 6 Roseburg, OR
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! (1,007 reviews)
"Very friendly staff. Beds, bathroom, and room overall was very clean, just the microwave that could have been cleaner. You could hear the TV and people talking next door, which was obnoxious, so the walls are pretty thin which isn't uncommon at hotels really."

Reviewed on Sep 15, 2025

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Super 8 by Wyndham 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! (1,005 reviews)
"Friendly staff"

Reviewed on Sep 15, 2025

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Sleep Inn & Suites Roseburg North Near Medical Center
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! (1,009 reviews)
"Staff were friendly, parking was easy, and walking distance to a couple food options. Rooms are a little dated, but cozy. Pillows are super comfortable."

Reviewed on Sep 17, 2025

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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! (1,003 reviews)
"Well appointed interior design and very comfortable bed"

Reviewed on Sep 9, 2025

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Holiday Inn Express Roseburg by IHG
See all 101 properties in Winston
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.