Search Cheap Flights toWinchester
Search 400 airlines and 321,000 hotels worldwide.
Stop Planning & Start Exploring
FREE 24 hour cancellation on most flights
Winchester Flights as Low as $156
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
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 September, 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 14 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 $156, 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 $156 right now, why wait?
Destination airport | Eugene |
Destination airport IATA code | EUG |
Roundtrip price | $156 |
Last Minute Hotel Deals in Winchester
Riverfront Inn Roseburg
Reviewed on Jul 14, 2025
Super 8 by Wyndham Roseburg
Reviewed on Jul 14, 2025
Holiday Inn Express Roseburg by IHG
Reviewed on Jul 11, 2025
Sleep Inn & Suites Roseburg North Near Medical Center
Reviewed on Jul 13, 2025
Motel 6 Roseburg, OR
Reviewed on Jul 14, 2025
Best Western Garden Villa Inn
Reviewed on Jul 13, 2025
Motel 6 Sutherlin, OR
Reviewed on Jun 27, 2025
Comfort Inn Roseburg
Reviewed on Jul 12, 2025
Nearby Cities
Popular Flight Routes
- Atlanta to New York
- Detroit to Las Vegas
- Dallas to Atlanta
- Dallas to Yosemite National Park
- Toronto to Edmonton
- Chicago to Tulum
- Houston to Lake Tahoe
- Chicago to Las Vegas
- Dallas to Miami
- Dallas to Lake Tahoe
- New York to Miami
- New York to Las Vegas
- Miami to Atlanta
- Minneapolis St Paul to Fort Walton Beach Destin
- Dallas to Branson
- Cleveland to Vero Beach
- Managua to Miami
- Atlanta to Boston
- Austin to Tulum
- Calgary to Vancouver
Flights to Our Favorite Destinations
- Flights to Las Vegas
- Flights to New York
- Flights to Orlando
- Flights to Myrtle Beach
- Flights to Chicago
- Flights to San Diego
- Flights to Panama City Beach
- Flights to Destin
- Flights to Ocean City
- Flights to Los Angeles
- Flights to Miami
- Flights to Boston
- Flights to Gulf Shores
- Flights to Nashville
- Flights to Atlantic City
- Flights to Pigeon Forge
Top Winchester Hotels
- Riverfront Inn Roseburg
- Super 8 by Wyndham Roseburg
- Holiday Inn Express Roseburg by IHG
- Sleep Inn & Suites Roseburg North Near Medical Center
- Motel 6 Roseburg, OR
- Best Western Garden Villa Inn
- Motel 6 Sutherlin, OR
- Comfort Inn Roseburg
- Quality Inn Central Roseburg
- Baymont by Wyndham Roseburg
- Howard Johnson by Wyndham Roseburg
- Rosewood Inn and Suites
- Best Western Plus Hartford Lodge
- Hampton Inn & Suites Roseburg