Search Cheap Flights to
Winchester

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Winchester Flights as Low as $351

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

American Airlines
United
Delta
Delta
United
United
United
Delta
United
Delta
United
Delta
Delta
Delta
Delta
Alaska Airlines

Cheap Flights to Winchester

Fall in love at first flight with your vacation to Winchester 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 Winchester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Winchester, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Winchester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winchester 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 EUG airport.

What is the cheapest month to fly to Winchester?

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 Winchester are in February, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winchester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Winchester.

What airport is best to fly into Winchester?

When you’re planning your trip to Winchester, convenience is the name of the game. Luckily, Winchester Southwest Oregon Regional Airport is nearby so you can deplane and get going on checking off everything on your Winchester must-do list.

How much are flights to Winchester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winchester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $351, 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 Winchester?

The trick to saving a stack of cash on your flight to Winchester? 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 $351 right now, why wait?

Winchester Flight Information
Destination airport
Eugene
Destination airport IATA code
EUG
Roundtrip price
$350

Last Minute Hotel Deals in Winchester

Riverfront Inn Roseburg
Riverfront Inn Roseburg
2 out of 5
315 W Harvard Ave, Roseburg, OR
The price is $102 per night from Jan 27 to Jan 28
$102
includes taxes & fees
Jan 27 - Jan 28
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! (1,243 reviews)
Wonderful
"Was impressed with the service and professionalism at front desk. Breakfast was also very nice. Thank you so very much for a nice stay"

Reviewed on Jan 21, 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 $79 per night from Feb 1 to Feb 2
$79
includes taxes & fees
Feb 1 - Feb 2
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)
"The hotel is dated but overall it was a positive experience. Staff was very helpful and courteous."

Reviewed on Jan 6, 2025

Sleep Inn & Suites Roseburg North Near Medical Center
Comfort Inn Roseburg
Comfort Inn Roseburg
2.5 out of 5
1539 NW Mullholland Drive, Roseburg, OR
The price is $88 per night from Jan 28 to Jan 29
$88
includes taxes & fees
Jan 28 - Jan 29
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! (1,002 reviews)
"Quiet room"

Reviewed on Jan 24, 2025

Comfort Inn 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
The price is $62 per night from Jan 28 to Jan 29
$62
includes taxes & fees
Jan 28 - Jan 29
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! (1,001 reviews)
Good value
"Clean, quiet, cheap. Easy highway access. Nice staff. Continental breakfast good."

Reviewed on Jan 20, 2025

Super 8 by Wyndham Roseburg
Best Western Garden Villa Inn
Best Western Garden Villa Inn
2.5 out of 5
760 NW Garden Valley Boulevard, Roseburg, OR
The price is $74 per night from Feb 2 to Feb 3
$74
includes taxes & fees
Feb 2 - Feb 3
Book a stay at this business-friendly hotel in Roseburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (1,002 reviews)
Good place
"This motel was clean, with microwave, refrigerator & coffeemaker Bed was comfortable Very good breakfast Eggs, sausage, potatoes"

Reviewed on Jan 21, 2025

Best Western Garden Villa Inn
Hampton Inn & Suites Roseburg
Hampton Inn & Suites Roseburg
2.5 out of 5
1620 Nw Mulholland Dr, Roseburg, OR
The price is $162 per night from Feb 2 to Feb 3
$162
includes taxes & fees
Feb 2 - Feb 3
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! (841 reviews)
Nice hotel in Roseburg!
"Updated, clean hotel with friendly staff!"

Reviewed on Jan 22, 2025

Hampton Inn & Suites Roseburg
Holiday Inn Express Roseburg, an IHG Hotel
Holiday Inn Express Roseburg, an IHG Hotel
2.5 out of 5
375 Harvard Blvd, Roseburg, OR
The price is $147 per night from Feb 1 to Feb 2
$147
includes taxes & fees
Feb 1 - Feb 2
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! (1,002 reviews)
"The property was nice and convenient. No major issues. The elevator could use some maintenance but overall it was fine. Breakfast was well-prepped and readily available."

Reviewed on Jan 21, 2025

Holiday Inn Express Roseburg, an IHG Hotel
Motel 6 Roseburg, OR
Motel 6 Roseburg, OR
2 out of 5
3100 Nw Aviation Dr, Roseburg, OR
The price is $55 per night from Feb 16 to Feb 17
$55
includes taxes & fees
Feb 16 - Feb 17
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. ...
7.2/10 Good! (1,000 reviews)
"The room was clean and comfortable, except for one mattress was worn out. Also, there was no shampoo, conditioner or lotion. The only other complaint I have is they didn’t have any kind of breakfast, not even a donut. On the plus side, it was very quiet and had a nice per area that was well lighted. ..."

Reviewed on Jan 18, 2025

Motel 6 Roseburg, OR
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.