
Winchester Holidays
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Your Winchester Holiday
The vibrant city of Winchester is calling. Delve into everything from its highlights to its hidden gems with a Winchester holiday package that's tailored to you. You'll want to do some exploring during your trip to Winchester. Swing by leading attractions such as Melrose Vineyards, Stewart Park and Douglas County Museum of History and Natural History. Expedia can help you escape the everyday. Tailor your holiday to Winchester to suit your travel style, whatever that may be!
Winchester Holiday
Winchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Max Temp Winter | 10ºC |
Max Temp Summer | 27ºC |
Top Sights | Wildlife Safari, Melrose Vineyards and Douglas County Museum of History and Natural History |
Our pick of the best Winchester Hotel Deals

Singing Waters at N. Umpqua
Roseburg North OR
10/10 Exceptional! (9 reviews)
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

Holiday Inn Express Roseburg by IHG
375 Harvard Blvd Roseburg OR
Fully refundable
The price is AU$167 per night from 28 Dec to 29 Dec
AU$167
28 Dec - 29 Dec
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
The place was nice and clean. The breakfast was varied enough for all people. I would stay there again.
Reviewed on 7 Dec 2025

Riverfront Inn Roseburg
315 W Harvard Ave Roseburg OR
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (1,423 reviews)
When you pull up to this place you could question if you are at the right location as the pictures are taken from the back of the property. The rooms are clean and comfortable. The choice of options for a free breakfast were good.
Reviewed on 11 Dec 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.











