Winchester Holidays

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Winchester Holiday

Our pick of the best Winchester Hotel Deals

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Roseburg North
10/10 Exceptional! (5 reviews)
Family Reunion
"This house was perfect for our annual family reunion about a mile past this house. We had our family all together and really enjoyed being close to family here. The house has a wonderful kitchen and great layout. We did not cook there as we had most of our family meals at farm up the road. I would ..."

Reviewed on 13 Jul. 2025

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Singing 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
8.4/10 Very Good! (1,357 reviews)
"Great no frills but comfy place and the river walk close by is great"

Reviewed on 20 Aug. 2025

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Riverfront Inn Roseburg
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
Fully refundableReserve now, pay when you stay
The price is NZ$198 per night from 21 Sept to 22 Sept
NZ$198
21 Sept - 22 Sept
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"I've stayed at this Sleep Inn a few times and always will when I'm in the arra."

Reviewed on 20 Aug. 2025

Sleep Inn & Suites Roseburg North Near Medical Center
See all 110 properties in Winchester
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.

Frequently asked questions

How much does a Winchester holiday package cost?
You can grab a holiday package to this destination on Expedia. But how much your holiday to Winchester costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Winchester?
January, February and November are great times to look for cheap Winchester holiday packages. Choosing to travel in less busy periods means you'll typically find better prices on hotels and flights.
How many days is enough for Winchester?
Usually, a handful of days is enough to explore the main sights during your Winchester holiday. But if you want to have time to unwind or take day tours, think about extending your trip.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Winchester package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchester adventure off to a flying start.
Is it cheaper to book a Winchester holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking hotels and flights individually. Better still, you can personalise your Winchester escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Winchester?
If you have your Winchester holiday dates locked in, book as early as you can to snap up some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Winchester?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Winchester.
  2. Plan your budget wisely: Besides the cost of your hotel, you should factor in other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that may come up during your trip to Winchester.
  3. Decide how long to go away for: Now that you know more about Winchester, you can figure out the right length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your airfare and accommodation: After you've settled on your dates and duration, lock in the right Winchester holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.