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Top Winchester hotels deals

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

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Stay at this vacation home in Roseburg North. Enjoy a beach locale, WiFi, and onsite parking. Popular attractions Winchester Dam and Becker Vineyard are located nearby. Discover genuine guest reviews for Singing Waters at N. Umpqua along with the latest prices and availability – book now.
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 $149 per night
CA $149
per night
May 13 - May 14
Stay at this motel 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 Stewart Park and Douglas County Museum of History and Natural History are located nearby. Discover genuine guest reviews for Riverfront Inn Roseburg along with the latest prices and availability – book now.
Pet-friendly
Pool
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 $118 per night
CA $118
per night
May 5 - May 6
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 Stewart Park and Winchester Dam are located nearby. Discover genuine guest reviews for Sleep Inn & Suites Roseburg North Near Medical Center along with the latest prices and availability – book now.
Hot tub
Pet-friendly
Comfort Inn Roseburg

Comfort Inn Roseburg

2.5 out of 5
1539 NW Mullholland Drive, Roseburg, OR
Free cancellation
Reserve now, pay when you stay
The price is CA $123 per night
CA $123
per night
May 12 - May 13
Stay at this golf hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Stewart Park and Douglas County Museum of History and Natural History are located nearby. Discover genuine guest reviews for Comfort Inn Roseburg along with the latest prices and availability – book now.
Hot tub
Pool
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 $97 per night
CA $97
per night
May 2 - May 3
Stay at this spa 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 Stewart Park and Winchester Dam are located nearby. Discover genuine guest reviews for Super 8 by Wyndham Roseburg along with the latest prices and availability – book now.
Pet-friendly
Pool
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 $123 per night
CA $123
per night
May 12 - May 13
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 Douglas County Museum of History and Natural History are located nearby. Discover genuine guest reviews for Best Western Garden Villa Inn along with the latest prices and availability – book now.
Hot tub
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?
Travelocity offers package deals to Winchester, including flights and hotels, starting at just . With all the cash you save, you could book some popular tours or maybe also tack on a couple of extra days to your exciting getaway.
Where can I get the best vacation package deals for Winchester?
Landing a great package deal to Winchester is easy with Travelocity. With access to 400 partner airlines and 665,000 properties around the world, you’ll have loads of choice when picking your hotels and flights.
Why should I book my Winchester vacation package with Travelocity?
Travel is all about making cherished memories and leaving all your stresses behind — which is why we provide you with a friendly team of customer service experts on hand around-the-clock should you need them. On top of that, our Price Match Guarantee ensures you’ll always get the best price available on our superb range of package deals. So what are you waiting for? There’s no time like the present to lock in the vacation you’ve always dreamed of.
Will I save money on my Winchester car rental if I combine it with a hotel or flight?
Certainly — and if you also add a tour or an experience to your Winchester vacation package, you’ll make even more savings. With an affordable package from Travelocity, you can find things to do in the area that are right up your alley. Then, jump in your rental car and work your way through the list. University of Oregon is one awesome sight to have a look at. You’ll find it 85 kilometersfrom Winchester.
What is the best time of year to go to Winchester?
Consider visiting in if you want to see this place at its most exciting. While they are the busiest few months, the buzzing energy that comes with the peak travel season is tough to resist. If you’d like a more laid-back pace, will appeal to you more. Don’t want to pay big bucks for a place to sleep? Avoid booking a room in , when prices usually surge. Look for someplace cozy and affordable in instead.
Can I go on vacation to Winchester at this time?
Our team has all the knowledge to help make your vacation dreams a reality, so before arranging your trip to Winchester, take a look at our Covid-19 Travel Advisor. This is where you can discover all the latest info about quarantine policies, travel restrictions and a whole lot more.