Search Cheap Flights to
Winston

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Winston Flights as Low as $99

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

United
Hawaiian Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Hawaiian Airlines
Hawaiian Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Hawaiian Airlines
United
Delta
Alaska Airlines
American Airlines
Bargain Flight

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 April, 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 $99, 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 $99 right now, why wait?

Winston Flight Information
Destination airport
Rogue Valley Intl.
Destination airport IATA code
MFR
Roundtrip price
$214

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!
SureStay by Best Western Roseburg

SureStay by Best Western Roseburg

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! (1,002 reviews)
Clean and staff is always nice.

Reviewed on Jan 30, 2026

SureStay by Best Western Roseburg
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! (1,425 reviews)
The staff were absolutely lovely, and the room was super clean. The only challenge for us was the bed was very hard which some people prefer otherwise a good stay.

Reviewed on Jan 26, 2026

Riverfront Inn 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! (1,000 reviews)
The place was clean, staff was friendly, breakfast was delicious, and the view was phenomenal!

Reviewed on Feb 1, 2026

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 ...
8/10 Very Good! (1,000 reviews)
Room was nice. Some wear & tear. Slow water flow for hot tub. Good breakfast.

Reviewed on Jan 25, 2026

Best Western Garden Villa Inn
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)
Clean room,courteous staff, pleasant stay

Reviewed on Jan 31, 2026

Super 8 by Wyndham 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! (977 reviews)
Front desk was fantastic. Pet fee steep. Room was clean and fresh. Great property. One star off for the insanely loud refrigerator cabinet door which banged every time closed because of no rubber bumper.

Reviewed on Jan 19, 2026

Hampton Inn & Suites Roseburg
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.