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Winston

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Winston Flights as Low as $143

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

Alaska Airlines
Tue, Aug 11 - Wed, Aug 19
SAN
San Diego Intl.
EUG
Eugene
$143 Roundtrip, found 14 hours ago
$143
Roundtrip
found 14 hours ago
Select Alaska Airlines flight, departing Tue, Aug 11 from San Diego Intl. to Eugene, returning Wed, Aug 19, priced at $143 found 14 hours ago
Alaska Airlines
Wed, Aug 5 - Wed, Aug 19
SAN
San Diego Intl.
EUG
Eugene
$146 Roundtrip, found 14 hours ago
$146
Roundtrip
found 14 hours ago
Select Alaska Airlines flight, departing Wed, Aug 5 from San Diego Intl. to Eugene, returning Wed, Aug 19, priced at $146 found 14 hours ago
Alaska Airlines
Tue, Aug 11 - Thu, Aug 20
SAN
San Diego Intl.
EUG
Eugene
$157 Roundtrip, found 14 hours ago
$157
Roundtrip
found 14 hours ago
Select Alaska Airlines flight, departing Tue, Aug 11 from San Diego Intl. to Eugene, returning Thu, Aug 20, priced at $157 found 14 hours ago
Alaska Airlines
Wed, Aug 5 - Sat, Aug 22
SAN
San Diego Intl.
EUG
Eugene
$160 Roundtrip, found 10 hours ago
$160
Roundtrip
found 10 hours ago
Select Alaska Airlines flight, departing Wed, Aug 5 from San Diego Intl. to Eugene, returning Sat, Aug 22, priced at $160 found 10 hours ago
Delta
Wed, Aug 5 - Sat, Aug 22
SAN
San Diego Intl.
EUG
Eugene
$198 Roundtrip, found 10 hours ago
$198
Roundtrip
found 10 hours ago
Select Delta flight, departing Wed, Aug 5 from San Diego Intl. to Eugene, returning Sat, Aug 22, priced at $198 found 10 hours ago
American Airlines
Wed, Aug 5 - Sat, Aug 22
SAN
San Diego Intl.
EUG
Eugene
$216 Roundtrip, found 10 hours ago
$216
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Wed, Aug 5 from San Diego Intl. to Eugene, returning Sat, Aug 22, priced at $216 found 10 hours ago
United
Wed, Aug 5 - Sat, Aug 22
SAN
San Diego Intl.
EUG
Eugene
$224 Roundtrip, found 10 hours ago
$224
Roundtrip
found 10 hours ago
Select United flight, departing Wed, Aug 5 from San Diego Intl. to Eugene, returning Sat, Aug 22, priced at $224 found 10 hours ago
United
Tue, Sep 22 - Tue, Sep 29
CLD
McClellan-Palomar
MFR
Rogue Valley Intl.
$257 Roundtrip, found 11 hours ago
$257
Roundtrip
found 11 hours ago
Select United flight, departing Tue, Sep 22 from McClellan-Palomar to Rogue Valley Intl., returning Tue, Sep 29, priced at $257 found 11 hours ago
Delta
Wed, Sep 9 - Wed, Sep 16
MCI
Kansas City Intl.
EUG
Eugene
$261 Roundtrip, found 3 hours ago
$261
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Sep 9 from Kansas City Intl. to Eugene, returning Wed, Sep 16, priced at $261 found 3 hours ago
Bargain Flight
Tue, Oct 20 - Sat, Oct 24
CVG
Cincinnati - Northern Kentucky Intl.
EUG
Eugene
$291 Roundtrip, found 12 hours ago
$291
Roundtrip
found 12 hours ago
Select Bargain Flight flight, departing Tue, Oct 20 from Cincinnati - Northern Kentucky Intl. to Eugene, returning Sat, Oct 24, priced at $291 found 12 hours ago
Bargain Flight
Fri, Nov 13 - Sat, Nov 14
CVG
Cincinnati - Northern Kentucky Intl.
MFR
Rogue Valley Intl.
$297 Roundtrip, found 6 days ago
$297
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Fri, Nov 13 from Cincinnati - Northern Kentucky Intl. to Rogue Valley Intl., returning Sat, Nov 14, priced at $297 found 6 days ago
Alaska Airlines
Tue, Aug 11 - Tue, Aug 11
ONT
Ontario Intl. Airport
MFR
Rogue Valley Intl.
$323 Roundtrip, found 2 days ago
$323
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Aug 11 from Ontario Intl. Airport to Rogue Valley Intl., returning Tue, Aug 11, priced at $323 found 2 days ago
Delta
Fri, Jul 3 - Tue, Jul 7
IAD
Washington Dulles Intl.
EUG
Eugene
$343 Roundtrip, found 13 hours ago
$343
Roundtrip
found 13 hours ago
Select Delta flight, departing Fri, Jul 3 from Washington Dulles Intl. to Eugene, returning Tue, Jul 7, priced at $343 found 13 hours ago
Alaska Airlines
Tue, Jul 14 - Tue, Jul 14
ONT
Ontario Intl. Airport
EUG
Eugene
$345 Roundtrip, found 12 hours ago
$345
Roundtrip
found 12 hours ago
Select Alaska Airlines flight, departing Tue, Jul 14 from Ontario Intl. Airport to Eugene, returning Tue, Jul 14, priced at $345 found 12 hours ago
American Airlines
Wed, Aug 5 - Sat, Aug 22
CLD
McClellan-Palomar
EUG
Eugene
$358 Roundtrip, found 18 hours ago
$358
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Wed, Aug 5 from McClellan-Palomar to Eugene, returning Sat, Aug 22, priced at $358 found 18 hours ago
United
Sat, Oct 24 - Fri, Oct 30
IAD
Washington Dulles Intl.
MFR
Rogue Valley Intl.
$446 Roundtrip, found 3 days ago
$446
Roundtrip
found 3 days ago
Select United flight, departing Sat, Oct 24 from Washington Dulles Intl. to Rogue Valley Intl., returning Fri, Oct 30, priced at $446 found 3 days ago

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 August, 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 14 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
Eugene
Destination airport IATA code
EUG
Roundtrip price
$205

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! (376 reviews)
"This was my second stay at the Safari Inn. Both times the owners are very friendly and nice. The motel is very well kept and comfortable."

Reviewed on Jun 1, 2026

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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 OR
Book a stay at this family-friendly cottage in Winston. Enjoy free parking and air conditioning. Popular attractions Wildlife Safari and South Umpqua River are ...
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

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Family-friendly Winston Vacation Rental w/ Deck!
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 ...
8/10 Very Good! (1,002 reviews)
"Dirty rooms, not maintained and dirty yards, not the best clientele. Lots of screaming and yelling in the rooms. Walls paper thin."

Reviewed on Jun 9, 2026

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Super 8 by Wyndham 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 ...
8.6/10 Excellent! (1,476 reviews)
"This was our second stay and it was just as wonderful as it was the first time. The young lady that checked us in was so helpful and pleasant, offering dining suggestions and walking path options. The room was very nice and the view from our balcony overlooked their beautiful garden and the Umpqua ..."

Reviewed on Jun 10, 2026

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Riverfront Inn Roseburg
The Lodge at Roseburg

The Lodge at Roseburg

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! (1,010 reviews)
"Marriott bought this a few months ago, but it has not been renovated yet. The photos were somewhat deceiving. Our stay was fine, but we expecting much more. Breakfast was good, but limited in offerings due to small breakfast area. We stayed four nights and if we wanted housekeeping, we had to ask ..."

Reviewed on Jun 9, 2026

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The Lodge at Roseburg
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! (1,011 reviews)
"It’s was ok for a one night stay, nothing fancy, sink had no stopper almost lost the cap to my hairspray, luckily I had tweezers to fish it out. Sink was incredibly low too, as we were put in an accessible room, which we did not request. Breakfast was pretty good. Again ok for a one night stay."

Reviewed on Jun 10, 2026

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Best Western Garden Villa Inn
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. ...
8.4/10 Very Good! (1,007 reviews)
"Even though the property was small and aging exterior, the rooms were surprisingly very clean ! Pool and hot tub were nice. Staff was very friendly. We canceled run down best western near by and stayed here !! Would stay again !"

Reviewed on Jun 10, 2026

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Comfort Inn Roseburg
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! (1,011 reviews)
"It was pretty good"

Reviewed on Jun 10, 2026

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SureStay by Best Western Roseburg
See all 109 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.