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Winston

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Winston Flights as Low as $121

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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 February, 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 15 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 $121, 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 $121 right now, why wait?

Winston Flight Information
Destination airport
Eugene
Destination airport IATA code
EUG
Roundtrip price
$137

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! (372 reviews)
Was just ok. One spontaneous night stay. Read the fine print on this property. They require a 100 $ cash deposit upon check in. He said it was just in case we smoked in the room. I guess that happens at a lower grade MOTEL. He was nice enough about it tho. Room seemed clean no funky smells. Would ...

Reviewed on Nov 12, 2025

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

Family-friendly Winston Vacation Rental w/ Deck!

3 out of 5
Winston OR
Book a stay at this 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! (1,424 reviews)
Checkin staff was very welcoming and gave great recommendations for dinner. The room could use an update but nothing that kept me from relaxing. The Riverfront Garden was a nice little walk

Reviewed on Jan 17, 2026

Riverfront Inn Roseburg
Hampton Inn & Suites Roseburg

Hampton Inn & Suites Roseburg

2.5 out of 5
1620 Nw Mulholland Dr Roseburg OR
Stay at this hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (969 reviews)
The room was great, I did mention that the fridge was not closed completely and was warm, this will also burn the motor out quickly. I closed it, went to dinner and was able to use it. Staff was great and so was our breakfast. Will stay here again.

Reviewed on Jan 4, 2026

Hampton Inn & Suites 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! (1,001 reviews)
Our room was very clean. The house keeping and the women at the front desk was so kind. She was very polite. We were there visiting family. Over all our stay was amazing . Would most definitely would come back.

Reviewed on Jan 14, 2026

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! (1,003 reviews)
Room was spotless. Breakfeast was good, overall property excellant upkeep. Staff very accommodating Highly recommend John B

Reviewed on Jan 13, 2026

Comfort 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! (1,003 reviews)
Good

Reviewed on Jan 3, 2026

Motel 6 Roseburg, OR
Travelodge by Wyndham Canyonville

Travelodge by Wyndham Canyonville

2 out of 5
554 SW Pine St Canyonville OR
Book a stay at this business-friendly hotel in Canyonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.4/10 Good! (496 reviews)
The toilet was not anchored and rocked when sat on. The smoke detector was missing. I did not report these items until I checked out and so did not give the staff the opportunity to change my room.

Reviewed on Jan 7, 2026

Travelodge by Wyndham Canyonville
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.