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 10 July to 11 July
AU$117
10 July - 11 July
includes taxes & fees
7.6/10 Good! (353 reviews)
"A quiet little place . Just right down the street from wildlife Safari ."

Reviewed on 30 Jun. 2025

Safari Inn
The Watusi Place - A Modern Umpqua Valley Getaway
The Watusi Place - A Modern Umpqua Valley Getaway
Winston
The price is AU$554 per night from 15 July to 16 July
AU$554
15 July - 16 July
includes taxes & fees
10/10 Exceptional! (36 reviews)
Family Suite
"This house is great for a family trip to the Wildlife Safari! The location is perfect and the property is suited to accommodate all ages with plenty of room to spread out. Family games, a place to grill, large kitchen and attention to detail from the cleaning team."

Reviewed on 22 Jun. 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
9.4/10 Exceptional! (56 reviews)
Spring break
"This was amazing stay. Great location, close to every place we wanted to go. It was very nice and clean. We will definitely be staying again."

Reviewed on 5 Apr. 2025

Get rates
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
See all 106 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$1,393
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.