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Winchester flight + hotel packages

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University Inn & Suites

University Inn & Suites

2 out of 5
East University
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Eugene (EUG)
Book a stay at this business-friendly motel in Eugene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hayward Field and Autzen Stadium are located nearby.
Valley River Inn

Valley River Inn

3.5 out of 5
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Denver (DEN) 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
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop 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.
Hayward Inn

Hayward Inn

3 out of 5
East University
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Eugene (EUG)
Stay at this 3-star business-friendly hotel in Eugene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Hayward Field and Autzen Stadium are located nearby.
The Florentine Waterfront Hotel

The Florentine Waterfront Hotel

2 out of 5
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Eugene (EUG)
Stay at this hotel in Westlake. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Siltcoos Lake and Jessie M. Honeyman State Park 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.
Kitchen
Washer
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 $142 per night
CA $142
CA $156 total
includes taxes & fees
Jun 2 - Jun 3
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.
Pool
Breakfast included
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 $141 per night
CA $141
CA $154 total
includes taxes & fees
Jun 29 - Jun 30
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.
Pool
Hot tub
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 $230 per night
CA $230
CA $251 total
includes taxes & fees
Jun 12 - Jun 13
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.
Pool
Breakfast included
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 $101 per night
CA $101
CA $111 total
includes taxes & fees
Jun 22 - Jun 23
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.
Pool
Breakfast included
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 $82 per night
CA $82
CA $91 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.
Pet-friendly
Parking included
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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 $516, 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