Winchester Vacations

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Find the Best Winchester Vacation Packages

Winchester Hotel Deals

Singing Waters at N. Umpqua
Singing Waters at N. Umpqua
Roseburg North
10/10 Exceptional! (5 reviews)
Stunning!
"Beautifully decorated house! Loved the view of the river in the backyard. So clean and new! No complaints!!"

Reviewed on 10 July 2024

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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
The price is SAR 402 per night from Apr 27 to Apr 28
SAR 402
SAR 440 total
includes taxes & fees
27 Apr - 28 Apr
8.4/10 Very Good! (1,263 reviews)
"Great peaceful location"

Reviewed on 19 April 2025

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 SAR 319 per night from May 11 to May 12
SAR 319
SAR 349 total
includes taxes & fees
11 May - 12 May
8/10 Very Good! (1,001 reviews)
"It was loud and average. Nothing special"

Reviewed on 12 April 2025

Sleep Inn & Suites Roseburg North Near Medical Center
See all 107 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 vacation package cost?
You can grab a vacation package to this destination on Expedia. But how much your vacation 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 vacation packages. Choosing to travel in less busy periods means you’ll typically find better prices on hotels and flights.
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 vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking hotels and flights individually. Better still, you can personalize 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 vacation package to Winchester?
If you have your Winchester vacation 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 accommodations: After you’ve settled on your dates and duration, lock in the right Winchester vacation package for you.