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 $157

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

Delta
Tue, Nov 18 - Thu, Nov 20
SFO
San Francisco Intl.
EUG
Eugene
$157 Roundtrip, found 13 hours ago
$157
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Nov 18 from San Francisco Intl. to Eugene, returning Thu, Nov 20, priced at $157 found 13 hours ago
Alaska Airlines
Tue, Nov 18 - Thu, Nov 20
SFO
San Francisco Intl.
EUG
Eugene
$159 Roundtrip, found 13 hours ago
$159
Roundtrip
found 13 hours ago
Select Alaska Airlines flight, departing Tue, Nov 18 from San Francisco Intl. to Eugene, returning Thu, Nov 20, priced at $159 found 13 hours ago
Hawaiian Airlines
Thu, Sep 18 - Thu, Sep 18
LAS
Harry Reid Intl.
EUG
Eugene
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Thu, Sep 18 from Harry Reid Intl. to Eugene, returning Thu, Sep 18, priced at $183 found 1 day ago
Alaska Airlines
Wed, Sep 17 - Wed, Sep 17
LAS
Harry Reid Intl.
EUG
Eugene
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, Sep 17 from Harry Reid Intl. to Eugene, returning Wed, Sep 17, priced at $183 found 1 day ago
Bargain Flight
Wed, Aug 6 - Sat, Aug 9
SMF
Sacramento Intl.
EUG
Eugene
$186 Roundtrip, found 17 hours ago
$186
Roundtrip
found 17 hours ago
Select Bargain Flight flight, departing Wed, Aug 6 from Sacramento Intl. to Eugene, returning Sat, Aug 9, priced at $186 found 17 hours ago
Bargain Flight
Wed, Sep 17 - Sat, Sep 20
LAS
Harry Reid Intl.
EUG
Eugene
$188 Roundtrip, found 17 hours ago
$188
Roundtrip
found 17 hours ago
Select Bargain Flight flight, departing Wed, Sep 17 from Harry Reid Intl. to Eugene, returning Sat, Sep 20, priced at $188 found 17 hours ago
Alaska Airlines
Wed, Sep 17 - Sat, Sep 20
LAS
Harry Reid Intl.
EUG
Eugene
$189 Roundtrip, found 17 hours ago
$189
Roundtrip
found 17 hours ago
Select Alaska Airlines flight, departing Wed, Sep 17 from Harry Reid Intl. to Eugene, returning Sat, Sep 20, priced at $189 found 17 hours ago
American Airlines
Wed, Sep 17 - Sat, Sep 20
LAS
Harry Reid Intl.
EUG
Eugene
$189 Roundtrip, found 17 hours ago
$189
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Wed, Sep 17 from Harry Reid Intl. to Eugene, returning Sat, Sep 20, priced at $189 found 17 hours ago
Alaska Airlines
Tue, Jun 17 - Sat, Jun 28
SAN
San Diego Intl.
EUG
Eugene
$195 Roundtrip, found 1 day ago
$195
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Jun 17 from San Diego Intl. to Eugene, returning Sat, Jun 28, priced at $195 found 1 day ago
United
Tue, Oct 7 - Tue, Oct 14
DFW
Dallas-Fort Worth Intl.
EUG
Eugene
$219 Roundtrip, found 5 hours ago
$219
Roundtrip
found 5 hours ago
Select United flight, departing Tue, Oct 7 from Dallas-Fort Worth Intl. to Eugene, returning Tue, Oct 14, priced at $219 found 5 hours ago
United
Tue, Nov 18 - Thu, Nov 20
SFO
San Francisco Intl.
EUG
Eugene
$249 Roundtrip, found 13 hours ago
$249
Roundtrip
found 13 hours ago
Select United flight, departing Tue, Nov 18 from San Francisco Intl. to Eugene, returning Thu, Nov 20, priced at $249 found 13 hours ago
Bargain Flight
Tue, Jun 24 - Wed, Jun 25
TUS
Tucson Intl.
EUG
Eugene
$275 Roundtrip, found 6 days ago
$275
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Tue, Jun 24 from Tucson Intl. to Eugene, returning Wed, Jun 25, priced at $275 found 6 days ago
Bargain Flight
Wed, Jun 18 - Sat, Jun 21
SJC
Norman Y. Mineta San Jose Intl.
EUG
Eugene
$365 Roundtrip, found 22 hours ago
$365
Roundtrip
found 22 hours ago
Select Bargain Flight flight, departing Wed, Jun 18 from Norman Y. Mineta San Jose Intl. to Eugene, returning Sat, Jun 21, priced at $365 found 22 hours ago
Bargain Flight
Wed, Jun 11 - Fri, Jun 20
OMA
Eppley Field
EUG
Eugene
$387 Roundtrip, found 20 hours ago
$387
Roundtrip
found 20 hours ago
Select Bargain Flight flight, departing Wed, Jun 11 from Eppley Field to Eugene, returning Fri, Jun 20, priced at $387 found 20 hours ago
Bargain Flight
Fri, May 30 - Tue, Jun 3
IAD
Washington Dulles Intl.
EUG
Eugene
$445 Roundtrip, found 1 day ago
$445
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Fri, May 30 from Washington Dulles Intl. to Eugene, returning Tue, Jun 3, priced at $445 found 1 day ago
American Airlines
Thu, Jun 19 - Sat, Jun 21
CLD
McClellan-Palomar
EUG
Eugene
$524 Roundtrip, found 23 hours ago
$524
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Thu, Jun 19 from McClellan-Palomar to Eugene, returning Sat, Jun 21, priced at $524 found 23 hours 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 November, 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 10 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 $157, 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 $157 right now, why wait?

Winchester Flight Information
Destination airport
Eugene
Destination airport IATA code
EUG
Roundtrip price
$156

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! (1,272 reviews)
"Excellent staff"

Reviewed on May 20, 2025

Get rates
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! (1,001 reviews)
Great place!
"Beautiful quiet hotel, with nice views of the city and mountains. I love it that the hot tub and pool are open until 11 PM. The only downside was the neighbor across the duck pond who turned his spot light right on our porch. I guess he didn’t like us sitting out on the balcony having a quiet conversation. ..."

Reviewed on May 9, 2025

Get rates
Holiday Inn Express Roseburg by IHG
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! (1,000 reviews)
"This is a good place to relax and get a good night's sleep after a long day."

Reviewed on May 17, 2025

Get rates
Sleep Inn & Suites Roseburg North Near Medical Center
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)
"Excellent customer service!"

Reviewed on May 22, 2025

Get rates
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
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 ...
8/10 Very Good! (1,006 reviews)
Good Customer Service & Clean
"Check in was easy & fast. Jupiter has a great personality & service at the front desk. The Room was clean, only thing that felt a little uncomfortable is the mattress bcoz it's was spring. The morning team at the front desk & breakfast team also offered great customer service."

Reviewed on May 10, 2025

Get rates
Best Western Garden Villa Inn
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)
"Staff was excellent especially night shift. Bed was very comfortable and nice mirrors. 5 stars"

Reviewed on May 22, 2025

Get rates
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. ...
8/10 Very Good! (1,000 reviews)
"Everything was excellent. The only things I found wrong in the room was the fridge was not clean it had some sticky stuff in it and there was dust on the headboards of the beds."

Reviewed on May 18, 2025

Get rates
Comfort Inn Roseburg
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)
"Great location. Rooms are really good, overall excellent."

Reviewed on May 17, 2025

Get rates
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.