Book Exclusive Winchester Vacation Packages

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Winchester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Florence Lighthouse Inn

Florence Lighthouse Inn

2.5 out of 5
Price was CA $1,201, price is now CA $1,051 per person
CA $1,051
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Eugene (EUG)
Stay at this motel in Florence. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Historic Old Town Florence and Siuslaw Pioneer Museum are located nearby.
Western Motel

Western Motel

2.5 out of 5
Price was CA $1,572, price is now CA $1,330 per person
CA $1,330
per person
Oct 15 - Oct 19
found 19 hours ago
Roundtrip flight included
Saskatoon (YXE) to Eugene (EUG)
Stay at this motel in Junction City. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Laurel Park and Star Theatre are located nearby.
Village Inn Springfield

Village Inn Springfield

3 out of 5
Price was CA $1,724, price is now CA $1,458 per person
CA $1,458
per person
Oct 15 - Oct 19
found 19 hours ago
Roundtrip flight included
Saskatoon (YXE) to Eugene (EUG)
Stay at this hotel in Springfield. 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 Autzen Stadium and Hayward Field are located nearby.
Ocean Breeze Motel

Ocean Breeze Motel

2 out of 5
Price was CA $1,281, price is now CA $1,139 per person
CA $1,139
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Eugene (EUG)
Stay at this motel in Florence. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sandland Adventures and Suislaw River Bridge are located nearby.
Holiday Inn Express Eugene - Springfield by IHG

Holiday Inn Express Eugene - Springfield by IHG

2.5 out of 5
Price was CA $2,028, price is now CA $1,849 per person
CA $1,849
per person
Oct 15 - Oct 19
found 19 hours ago
Roundtrip flight included
Saskatoon (YXE) 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 Cinemark Eugene Springfield 17 are located nearby.

Top Winchester hotels deals

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 $103 per night
CA $103
CA $113 total
Sep 15 - Sep 16
includes taxes & fees
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
Hot tub
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 $120 per night
CA $120
CA $132 total
Aug 25 - Aug 26
includes taxes & fees
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
Best Western Garden Villa Inn

Best Western Garden Villa Inn

2.5 out of 5
760 NW Garden Valley Boulevard Roseburg OR
Free cancellation
Reserve now, pay when you stay
The price is CA $152 per night
CA $152
CA $167 total
Sep 6 - Sep 7
includes taxes & fees
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
Hot tub
SureStay by Best Western Roseburg

SureStay by Best Western Roseburg

2.5 out of 5
2855 NW Edenbower Blvd Roseburg OR
Free cancellation
Reserve now, pay when you stay
The price is CA $154 per night
CA $154
CA $168 total
Aug 30 - Aug 31
includes taxes & fees
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
Breakfast included
Holiday Inn Express & Suites Roseburg North by IHG

Holiday Inn Express & Suites Roseburg North by IHG

2.5 out of 5
1530 NW Mulholland Drive Roseburg OR
Free cancellation
The price is CA $256 per night
CA $256
CA $281 total
Aug 29 - Aug 30
includes taxes & fees
Stay at this hotel in Roseburg. Enjoy free breakfast, free parking, and a 24-hour fitness center. Popular attractions Umpqua Valley Tennis Center and Stewart Park are located nearby.
Pool
Breakfast included
Best Western Plus Hartford Lodge

Best Western Plus Hartford Lodge

2.5 out of 5
150 Myrtle St Sutherlin OR
Free cancellation
Reserve now, pay when you stay
The price is CA $198 per night
CA $198
CA $217 total
Sep 13 - Sep 14
includes taxes & fees
Book a stay at this business-friendly hotel in Sutherlin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Umpqua Golf Resort and Central Park are located nearby.
Breakfast included
Pet-friendly
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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 $1,051, 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

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