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

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

Get rates
Singing Waters at N. Umpqua
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$149 per night from 19 July to 20 July
AU$149
19 July - 20 July
includes taxes & fees
8/10 Very good! (1,001 reviews)
"Hot tub was 85 degrees. Door to the outside by my room didn’t allow me to enter. No breakfast to speak of."

Reviewed on 30 June 2026

Super 8 by Wyndham Roseburg
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 AU$159 per night from 5 July to 6 July
AU$159
5 July - 6 July
includes taxes & fees
8.6/10 Excellent! (1,473 reviews)
"Great little diamond in the rough! Perfect for weary travelers at a very reasonable rate where we oniy need a comfortable nguts sleep. The bonus was rhe continental breakfast. Old and dated but clean, comfortable and well maintained inside and out."

Reviewed on 1 July 2026

Riverfront Inn Roseburg
See all 122 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.

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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.