Winston Holidays

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Your Winston Holiday

Well known for its rural countryside and friendly locals, Winston is a perfect getaway destination. Lock in one of our Winston holiday packages and uncover all that this impressive city has to offer. A trip to Winston is an ideal opportunity to go sightseeing. Check out big-name attractions such as Wildlife Safari, South Umpqua River and Douglas County Museum of History and Natural History. Whoever you're escaping with and whatever you want to spend, your dream Winston holiday is just a few clicks away with Expedia.

Winston Holiday

Winston Essential Information

Language
English
Currency
U.S dollars
Population
5,400
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 Winston Hotel Deals

Safari Inn

Safari Inn

2 out of 5
101 NE Main Street, Winston, OR
Fully refundableReserve now, pay when you stay
The price is AU$117 per night from 2 Sept to 3 Sept
AU$117
2 Sept - 3 Sept
includes taxes & fees
7.6/10 Good! (359 reviews)
Bang for my buck
"Great room for my budget. Needed a place to just sleep in during a long road trip. I was very pleased with the comfort and cleanliness of the room, as well as the amenities. Very happy!!"

Reviewed on 17 Aug. 2025

Safari Inn
The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston
The price is AU$608 per night from 7 Sept to 8 Sept
AU$608
7 Sept - 8 Sept
includes taxes & fees
10/10 Exceptional! (40 reviews)
"Such a cute house in a nice, quiet neighborhood! The layout was perfect for our family, with plenty of space to relax and feel at home. Leah truly thought of everything we might need—so thoughtful and well-stocked. Check-in and check-out were a breeze. We really enjoyed our stay!"

Reviewed on 1 Aug. 2025

The Watusi Place - A Modern Umpqua Valley Getaway
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Winston
9.6/10 Exceptional! (57 reviews)
Great Home
"This is an excellent home for a couple or group. We had three generations and were so comfortable. The kitchen, living room, dining room is one very large room totally open so we were able to always be together. Owners are very responsive. I highly recommend this home. My husband and I plan on renting ..."

Reviewed on 25 Jun. 2025

Get rates
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
See all 99 properties in Winston
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

What to do in Winston

4 Day Ngorongoro Crater Tarangire and Serengeti National Park

4 Day Ngorongoro Crater Tarangire and Serengeti National Park

AU$1,377
per adult
4 Day Ngorongoro Crater Tarangire and Serengeti National Park
See all activities in Winston

Frequently asked questions

How much does a Winston holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Winston costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Winston?
To score cheap Winston holiday packages, plan your trip outside of busy periods like public holidays and major events. You'll typically find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Winston?
The ideal length of your Winston holiday depends on what you'd like to do. Generally, a few days to a week will give you plenty of time to visit all the major sights and discover some hidden treasures along the way.
How to find the best Winston package deals?
Landing a cheap Winston package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply some filters and see what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most affordable Winston package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winston holiday as a package?
An Expedia holiday package could land you great savings when compared to booking accommodation and flights individually. Better still, you can tailor your Winston escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Winston?
Enjoy fantastic discounts by booking your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Winston escape.
How to plan a trip to Winston?

  1. Choose when to get away: Check your diary and get packing. Your favourite season and the type of activities available will also help you decide when to holiday in Winston.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to activities and flights. Your accommodation will probably be the biggest expense during your trip to Winston.
  3. Decide your trip length: Think about how much time you'd like to spend exploring Winston. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Winston holiday package.

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