Winchester Holiday Packages

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So, what's stopping you? Book soon and save up to . All you have to do is mix and match from more than 550 partner airlines and 665,000 properties.

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Winchester Accommodation

Have a look at Wotif's clever map tool to pinpoint where you'd prefer to base yourself during your time in Winchester. There are currently no properties in the middle of the neighbourhood. However, there are 14 accommodations near Winchester.

Been given the task of finding a place to stay? Don't waste precious time Googling — we can help you out. Our top suggestions for this locale are the Holiday Inn Express Roseburg (375 Harvard Blvd) and the Best Western Garden Villa Inn (760 NW Garden Valley Boulevard).

Car Hire in Winchester

You'll have a hard time securing a car in the heart of town. We'd suggest travelling out to Enterprise in the close-by neighbourhood of Roseburg. It's located at 150 Ne Garden Valley Blvd, 2 kilometres from the downtown area.

Holidays to Winchester

Traffic jams, work meetings, endless bills. It's time to forget about all those mundane things and turn your attention to something way more fun — organising your adventure in Winchester. Ready to get started with a few basics?

A neighbourhood in Roseburg, Winchester is a fantastic base from which to discover this city. To get there from the downtown area, chuck your gear in the boot of a taxi and journey north for 8 kilometres.

Solo travellers won't be by themselves for too long in Winchester. With Roseburg's population standing at roughly 21 000, you're bound to make a heap of new friends while you're here.

Top Winchester hotels

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Roseburg North
Singing Waters at N. Umpqua: Holiday home with WiFi and parking. Located on the waterfront.
"The pictures are exactly how you will find this home. The remodel is first class, the river view amazing. A native of Roseburg, our family stayed here while visiting family. Very peaceful..hosts were very responsive."

Reviewed on 12 Sept 2025

Opens in a new windowSinging Waters at N. Umpqua
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave, Roseburg, OR
Fully refundableReserve now, pay when you stay
Riverfront Inn Roseburg: Pet-friendly motel with free breakfast and free WiFi. Located in the city centre.
"Don’t let the outside fool you. It’s clean & well appointed. Be sure to get a room on the backside. Less road noise."

Reviewed on 22 Sept 2025

Opens in a new windowRiverfront Inn Roseburg
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
Fully refundableReserve now, pay when you stay
The price is AU$131 per night from 8 Oct to 9 Oct
AU$131
8 Oct - 9 Oct
includes taxes & fees
Super 8 by Wyndham Roseburg: Pet-friendly hotel with free breakfast and free WiFi. Located near the airport.
"We found it satisfactory in all the basics."

Reviewed on 21 Sept 2025

Opens in a new windowSuper 8 by Wyndham Roseburg
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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.