Winston Vacations

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    Save up to ₩234,741 when you book a flight and hotel together*
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Find the Best Winston Vacation Packages

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 ₩96,859 per night from Sep 2 to Sep 3
₩96,859
₩105,092 total
Sep 2 - Sep 3
includes taxes & fees
7.6/10 Good! (357 reviews)
"I would like to thank Rick from staff for the outstanding reception and support during my stay"

Reviewed on Aug 5, 2025

Safari Inn
Family-friendly Winston Vacation Rental w/ Deck!

Family-friendly Winston Vacation Rental w/ Deck!

3 out of 5
Winston
"This house was beautiful, affordable, and very spacious! It had every single amenity you would need and many extras too! The host was extremely attentive and informative with check on and out process and also making sure we could contact her at any time if needed. I definitely recommend this house ..."

Reviewed on Apr 5, 2024

Get rates
Family-friendly Winston Vacation Rental w/ Deck!
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 ₩141,968 per night from Sep 1 to Sep 2
₩141,968
₩155,459 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,360 reviews)
"The check-in staff is so great here! Beds are always comfortable & clean, and I like the grassy sitting area by the river. Cleanliness in the rest of the room seems to be hit or miss (squished bugs on a wall, debris in the upholstered chair, dust all over the side-table, etc.) and during my last ..."

Reviewed on Aug 9, 2025

Riverfront Inn Roseburg
See all 101 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.

Discover the most popular places to visit in Winston

The Wildlife Safari is such an awesome place! It has been around for 38 years and was one of my favorite places I ever visited as a child. My children feel the same after visiting in the summer of 2014. This 600 acre park is home to over 500 animals and features a drive through park as well as a walk through viewing area, cafe and gift shop. One of our favorite parts is in a particular area of the drive-thru park, you can buy food and feed the animals which are emus and different types of deer from your car. Get your camera ready as hilarity ensues! http://www.wildlifesafari.net

Wildlife Safari

Why not see the exotic and native animals who live at Wildlife Safari during your vacation in Winston? While you're in the area, stroll along the riverfront.

Wildlife Safari

Frequently asked questions

How much does a Winston vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Winston costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Winston?
To score cheap Winston vacation 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 vacation 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 vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations 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 vacation 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 favorite season and the type of activities available will also help you decide when to vacation in Winston.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to activities and flights. Your accommodations 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 vacation package.

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