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Winchester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Valley River Inn

Valley River Inn

3.5 out of 5
per person
Jul 7 - Jul 10
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Eugene (EUG)
Stay at this 3.5-star family-friendly hotel in Eugene. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the comfy rooms in our reviews. Popular attractions Autzen Stadium and Hayward Field are located nearby.
Graduate by Hilton Eugene

Graduate by Hilton Eugene

4 out of 5
Downtown Eugene
per person
Jul 7 - Jul 10
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Eugene (EUG)
Stay at this 4-star golf hotel in Eugene. Enjoy free WiFi, a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Autzen Stadium and Hayward Field are located nearby.
Holiday Inn Express Eugene - Springfield by IHG

Holiday Inn Express Eugene - Springfield by IHG

2.5 out of 5
per person
Jul 7 - Jul 10
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Eugene (EUG)
Book a stay at this business-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Autzen Stadium and Hayward Field are located nearby.
Courtyard by Marriott Eugene Springfield

Courtyard by Marriott Eugene Springfield

3 out of 5
per person
Jul 7 - Jul 10
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Eugene (EUG)
Stay at this 3-star business-friendly hotel in Springfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Autzen Stadium and Hayward Field are located nearby.
Residence Inn Eugene Springfield

Residence Inn Eugene Springfield

3 out of 5
Cal Young
per person
Jul 7 - Jul 10
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Eugene (EUG)
Stay at this 3-star business-friendly hotel in Eugene. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Autzen Stadium and Hayward Field are located nearby.

Top Winchester hotels deals

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Get rates
Stay at this vacation home in Roseburg North. Enjoy a beach locale, laundry facilities, and balconies. Popular attractions Winchester Dam and Becker Vineyard are located nearby.
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave, Roseburg, OR
Free cancellation
Reserve now, pay when you stay
The price is CA $141 per night
CA $141
CA $155 total
includes taxes & fees
Jun 10 - Jun 11
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 attractions Stewart Park and Douglas County Museum of History and Natural History are located nearby.
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
Free cancellation
Reserve now, pay when you stay
The price is CA $134 per night
CA $134
CA $147 total
includes taxes & fees
Jun 16 - Jun 17
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 in our reviews. Popular attractions Umpqua Valley Tennis Center and Stewart Park are located nearby.
Holiday Inn Express Roseburg by IHG

Holiday Inn Express Roseburg by IHG

2.5 out of 5
375 Harvard Blvd, Roseburg, OR
Free cancellation
The price is CA $216 per night
CA $216
CA $236 total
includes taxes & fees
Jun 15 - Jun 16
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 in our reviews. Popular attractions Stewart Park and Umpqua Valley Tennis Center are located nearby.
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
Free cancellation
Reserve now, pay when you stay
The price is CA $99 per night
CA $99
CA $109 total
includes taxes & fees
Jun 8 - Jun 9
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 rooms in our reviews. Popular attractions Umpqua Valley Tennis Center and Stewart Park are located nearby.
Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

2 out of 5
1400 Hospitality Way, Sutherlin, OR
Free cancellation
Reserve now, pay when you stay
The price is CA $93 per night
CA $93
CA $103 total
includes taxes & fees
Jun 22 - Jun 23
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. Popular attractions Umpqua Golf Resort and Central Park are located nearby.
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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.

Winchester Vacations

Get your trip off to the best possible start by knowing a thing or two about Winchester before you jet off.

From downtown Roseburg, you'll need to make your way north for 5 miles (8 kilometers) to get to this neighborhood.

Ready to meet some of the locals? 21,000 people live in Roseburg.

Hotels in Winchester

After a long day exploring Winchester, you'll need someplace comfortable to catch up on some sleep. While it's difficult to stay in the center of this neighborhood, it is possible to spend your evenings at one of the 14 properties a quick commute away.

The Holiday Inn Express Roseburg (375 Harvard Blvd) and the Best Western Garden Villa Inn (760 NW Garden Valley Boulevard) are our suggestions for this neighborhood.

Places to visit in Winchester

Ready for some snowboarding? It's one of the best activities in the wider region and a fantastic excuse to spend time in nature. Skiing is one more activity to include on your to-do list.

Where do you fly into for Winchester?

Touching down at Southwest Oregon Regional Airport (OTH)? Winchester is 45 miles (72 kilometers) away. Grab a cup of coffee, secure a ride and you'll be there in no time!

Frequently asked questions

How much are vacation packages to Winchester?
Starting from as low as CA $748, hotel and flight packages are an excellent way to stretch your travel budget. Winchester, here you come!
Where can I get the best vacation package deals for Winchester?
Snapping up the perfect package deal to Winchester is a piece of cake with Travelocity. With as many as 400 airlines and 1,000,000 properties all over the globe, you’re spoiled for choice when selecting your flights and hotels.
Why should I book my Winchester vacation bundle via Travelocity?
Savings, support and a stress-free booking are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on our team of customer support experts around-the-clock. With the Travelocity Price Match Guarantee, you know you’re getting the best deal available.
Can I save money on my Winchester car rental if I bundle it with hotels and flights?
You sure can with our Winchester vacation packages. With one of these, there are lots of ways to make your vacation budget go further. Bundle any two or more car, hotel, flight and tour bookings and see the savings pile up. With a rental car, all the key sights in and around Winchester are just a road trip away.
Which airport is best for Winchester?
Southwest Oregon Regional Airport (OTH), the primary terminal in Winchester, is where you’ll stroll through arrivals. You’ll find it 72 kilometers west of the center of town.
Where should I stay when visiting Winchester?
Many travelers hit the hay at the Singing Waters at N. Umpqua. It’s a great base for your Winchester getaway.

Photos of local treasures

Browse Winchester vacation photos for more inspiration