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Winston

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Winston Flights as Low as $251

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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 May, 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 $251, 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 $251 right now, why wait?

Winston Flight Information
Destination airport
Eugene
Destination airport IATA code
EUG
Roundtrip price
$156

Last Minute Hotel Deals in Winston

Safari Inn
Safari Inn
2 out of 5
101 NE Main Street, Winston, OR
The price is $65 per night from May 5 to May 6
$65
includes taxes & fees
May 5 - May 6
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! (345 reviews)
"Everything"

Reviewed on Apr 22, 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 cottage in Winston. Enjoy free parking and air conditioning. Popular attractions Wildlife Safari and South Umpqua River are located ...
10/10 Exceptional! (1 review)
"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!
Wildlife Inn
Wildlife Inn
2 out of 5
251 N Main St, Winston, OR
Book a stay at this business-friendly hotel in Winston. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Wildlife Safari and South Umpqua ...
8.4/10 Very Good! (379 reviews)
"This property was closed for renovations. We arrived and had to find other accomodations. The staff were very friendly in pointing us to other options."

Reviewed on Apr 16, 2021

Wildlife Inn
Riverfront Inn Roseburg
Riverfront Inn Roseburg
2 out of 5
315 W Harvard Ave, Roseburg, OR
The price is $122 per night from May 4 to May 5
$122
includes taxes & fees
May 4 - May 5
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! (1,258 reviews)
"Great!"

Reviewed on Apr 29, 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
The price is $93 per night from May 18 to May 19
$93
includes taxes & fees
May 18 - May 19
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! (1,000 reviews)
"A good value for the money. Front desk personnel were all very professional, cheerful, and competent."

Reviewed on Apr 29, 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
The price is $76 per night from May 7 to May 8
$76
includes taxes & fees
May 7 - May 8
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 ...
7.6/10 Good! (1,000 reviews)
"Decent hotel for the price. Room was clean and remodeled however the hallways reeked of that horrible Lysol disinfectant spray."

Reviewed on Apr 24, 2025

Super 8 by Wyndham Roseburg
Comfort Inn Roseburg
Comfort Inn Roseburg
2.5 out of 5
1539 NW Mullholland Drive, Roseburg, OR
The price is $101 per night from May 9 to May 10
$101
includes taxes & fees
May 9 - May 10
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. ...
8/10 Very Good! (1,000 reviews)
"Staff always friendly and outgoing."

Reviewed on Apr 23, 2025

Comfort Inn Roseburg
Holiday Inn Express Roseburg by IHG
Holiday Inn Express Roseburg by IHG
2.5 out of 5
375 Harvard Blvd, Roseburg, OR
The price is $148 per night from May 11 to May 12
$148
includes taxes & fees
May 11 - May 12
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)
"Good price for a great setting. Staff are friendly and good selection for breakfast."

Reviewed on Apr 28, 2025

Holiday Inn Express Roseburg by IHG
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.