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Winchester

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Winchester Flights as Low as $135

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

American Airlines
Sat, Jul 12 - Wed, Jul 16
PHX
Sky Harbor Intl.
EUG
Eugene
$135 Roundtrip, found 2 hours ago
$135
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Jul 12 from Sky Harbor Intl. to Eugene, returning Wed, Jul 16, priced at $135 found 2 hours ago
Delta
Sat, Jul 12 - Wed, Jul 16
PHX
Sky Harbor Intl.
EUG
Eugene
$143 Roundtrip, found 2 hours ago
$143
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, Jul 12 from Sky Harbor Intl. to Eugene, returning Wed, Jul 16, priced at $143 found 2 hours ago
Alaska Airlines
Mon, Jul 14 - Wed, Jul 16
PHX
Sky Harbor Intl.
EUG
Eugene
$144 Roundtrip, found 3 days ago
$144
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Mon, Jul 14 from Sky Harbor Intl. to Eugene, returning Wed, Jul 16, priced at $144 found 3 days ago
American Airlines
Sat, Jul 12 - Tue, Jul 15
PHX
Sky Harbor Intl.
EUG
Eugene
$161 Roundtrip, found 4 days ago
$161
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Jul 12 from Sky Harbor Intl. to Eugene, returning Tue, Jul 15, priced at $161 found 4 days ago
Alaska Airlines
Thu, Jul 31 - Tue, Aug 5
PHX
Sky Harbor Intl.
EUG
Eugene
$168 Roundtrip, found 2 days ago
$168
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Thu, Jul 31 from Sky Harbor Intl. to Eugene, returning Tue, Aug 5, priced at $168 found 2 days ago
American Airlines
Sat, Jul 12 - Wed, Jul 16
PHX
Sky Harbor Intl.
EUG
Eugene
$171 Roundtrip, found 2 hours ago
$171
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Jul 12 from Sky Harbor Intl. to Eugene, returning Wed, Jul 16, priced at $171 found 2 hours ago
Delta
Mon, Jul 7 - Thu, Jul 10
PHX
Sky Harbor Intl.
EUG
Eugene
$172 Roundtrip, found 2 days ago
$172
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Jul 7 from Sky Harbor Intl. to Eugene, returning Thu, Jul 10, priced at $172 found 2 days ago
Delta
Sun, Jul 13 - Fri, Jul 18
PHX
Sky Harbor Intl.
EUG
Eugene
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Jul 13 from Sky Harbor Intl. to Eugene, returning Fri, Jul 18, priced at $174 found 2 days ago
United
Sun, Aug 31 - Sat, Sep 6
ONT
Los Angeles - Ontario Intl.
EUG
Eugene
$174 Roundtrip, found 1 day ago
$174
Roundtrip
found 1 day ago
Select United flight, departing Sun, Aug 31 from Los Angeles - Ontario Intl. to Eugene, returning Sat, Sep 6, priced at $174 found 1 day ago
Alaska Airlines
Sun, Aug 31 - Sat, Sep 6
ONT
Los Angeles - Ontario Intl.
EUG
Eugene
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sun, Aug 31 from Los Angeles - Ontario Intl. to Eugene, returning Sat, Sep 6, priced at $177 found 1 day ago
Hawaiian Airlines
Sat, Jul 5 - Sat, Jul 12
PHX
Sky Harbor Intl.
EUG
Eugene
$182 Roundtrip, found 2 days ago
$182
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Sat, Jul 5 from Sky Harbor Intl. to Eugene, returning Sat, Jul 12, priced at $182 found 2 days ago
Bargain Flight
Mon, Sep 1 - Wed, Sep 3
LAX
Los Angeles Intl.
EUG
Eugene
$187 Roundtrip, found 2 days ago
$187
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Mon, Sep 1 from Los Angeles Intl. to Eugene, returning Wed, Sep 3, priced at $187 found 2 days ago
American Airlines
Thu, Sep 4 - Thu, Sep 11
LAX
Los Angeles Intl.
EUG
Eugene
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Sep 4 from Los Angeles Intl. to Eugene, returning Thu, Sep 11, priced at $197 found 2 hours ago
Delta
Tue, Aug 12 - Wed, Aug 20
MCO
Orlando Intl.
EUG
Eugene
$235 Roundtrip, found 3 days ago
$235
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Aug 12 from Orlando Intl. to Eugene, returning Wed, Aug 20, priced at $235 found 3 days ago
Hawaiian Airlines
Tue, Sep 16 - Wed, Sep 17
DEN
Denver Intl.
EUG
Eugene
$238 Roundtrip, found 1 day ago
$238
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Tue, Sep 16 from Denver Intl. to Eugene, returning Wed, Sep 17, priced at $238 found 1 day ago
Bargain Flight
Mon, Jun 16 - Sat, Jun 21
BUR
Hollywood Burbank
EUG
Eugene
$346 Roundtrip, found 1 day ago
$346
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Mon, Jun 16 from Hollywood Burbank to Eugene, returning Sat, Jun 21, priced at $346 found 1 day ago

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 July, 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 $135, 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 $135 right now, why wait?

Winchester Flight Information
Destination airport
Eugene
Destination airport IATA code
EUG
Roundtrip price
$134

Last Minute Hotel Deals in Winchester

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! (1,293 reviews)
"Very friendly staff. Comfortable accommodations. Great view."

Reviewed on Jun 10, 2025

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Riverfront Inn 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 WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (1,001 reviews)
"Everything was nice. The only criticism is with expedia lacking clearer outlines on what particular rooms at a hotel are and are not pet friendly."

Reviewed on May 30, 2025

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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 ...
7.6/10 Good! (1,001 reviews)
"Good value for Expedia price. Good beds. A new paint job in the hallways to get rid of the lime green color would take away the dated look."

Reviewed on Jun 9, 2025

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Super 8 by Wyndham Roseburg
Motel 6 Sutherlin, OR
Motel 6 Sutherlin, OR
2 out of 5
1400 Hospitality Way, Sutherlin, OR
Stay at this motel in Sutherlin. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (1,000 reviews)
"Clean and neat. Will come back."

Reviewed on Jun 11, 2025

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Motel 6 Sutherlin, OR
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. ...
8.2/10 Very Good! (1,001 reviews)
"Clean rooms. Staff was friendly."

Reviewed on Jun 11, 2025

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Comfort 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
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! (1,004 reviews)
Our go-to in Roseburg
"We stayed here for 2 days while visiting family in the area. It's not the first time we've stayed and the quality is still top of the line. Clean, well appointed rooms, very comfortable beds and the staff is wonderful."

Reviewed on Jun 13, 2025

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Sleep Inn & Suites Roseburg North Near Medical Center
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! (1,002 reviews)
"Good breakfast"

Reviewed on Jun 11, 2025

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Holiday Inn Express Roseburg by IHG
Motel 6 Roseburg, OR
Motel 6 Roseburg, OR
2 out of 5
3100 Nw Aviation Dr, Roseburg, OR
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. ...
7.4/10 Good! (1,000 reviews)
"Standard motel room. Bathtub was weird shape and was not compatible with a “soak”. Disappointing. Also, housekeeping attitude is questionable. We did not get fresh towel. I had to ask at front desk. The clerk apologized and immediately got us fresh towels. Overall, it was OK but I may look elsewhere ..."

Reviewed on Jun 1, 2025

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Motel 6 Roseburg, OR
See all 109 properties in Winchester
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.