Winston Vacations from $404

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Your Winston Vacation

From its rural countryside to its friendly locals and beyond, there's plenty to like about Winston. Uncover the wonders of this awesome city with a Winston vacation package that's made for you. Wildlife Safari, South Umpqua River and Douglas County Museum of History and Natural History are just some of the attractions you'll want to explore during your trip to Winston. Expedia will help you escape the everyday. Tailor your vacation to Winston to match your travel style, whatever that may be.

The Latest Winston vacation packages

Price found within the past 48 hours. Click for updated prices.
Anchor Bay Inn

Anchor Bay Inn

2.5 out of 5
per person
Aug 9 - Aug 13
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to North Bend (OTH)
6.6/10 (708 reviews)
Last minute reservations.

Reviewed on Jul 6, 2025

Beachfront Inn

Beachfront Inn

2.5 out of 5
per person
Aug 17 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to North Bend (OTH)
9/10 Wonderful! (1,010 reviews)
Needs some paint and we did have smokers next door. I’m sure they knew that it was a non smoking motel. Pretty beach!

Reviewed on Jul 4, 2025

Bandon Inn

Bandon Inn

3 out of 5
per person
Aug 17 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to North Bend (OTH)
9.4/10 Exceptional! (1,198 reviews)
We stayed on the 4th of July and had a view of fireworks from our room.

Reviewed on Jul 6, 2025

Castillo di Sabbia

Castillo di Sabbia

2 out of 5
per person
Aug 17 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to North Bend (OTH)
No reviews
Tu Tu Tun Lodge

Tu Tu Tun Lodge

5 out of 5
per person
Aug 14 - Aug 18
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to North Bend (OTH)
9.2/10 Wonderful! (13 reviews)
Very nice setting. great service, food and Drink

Reviewed on Jul 3, 2025

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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

4.5/5(110 reviews)

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

Abacela Winery

4.5/5(11 reviews)

You can enjoy a tasting or tour at Abacela Winery during your travels to Winston. While you're in the area, stroll along the riverfront.

Abacela Winery

What to do in Winston

4 Day Ngorongoro Crater Tarangire and Serengeti National Park

4 Day Ngorongoro Crater Tarangire and Serengeti National Park

$899
per adult
4 Day Ngorongoro Crater Tarangire and Serengeti National Park
See all activities in Winston

Winston Hotel Deals

Safari Inn
Safari Inn
2 out of 5
101 NE Main Street, Winston, OR
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $76 total per night from Jul 8 to Jul 9
$76 total
Jul 8 - Jul 9
Total includes taxes and fees
7.6/10 Good! (353 reviews)
"A quiet little place . Just right down the street from wildlife Safari ."

Reviewed on Jun 30, 2025

Safari Inn
The Watusi Place - A Modern Umpqua Valley Getaway
The Watusi Place - A Modern Umpqua Valley Getaway
Winston
$332 nightly
The price is $360 total per night from Jul 15 to Jul 16
$360 total
Jul 15 - Jul 16
Total includes taxes and 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 Jun 22, 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 Apr 5, 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.

Find the Best Winston Vacation Packages

Winston Essential Information

Language
English
Currency
U.S dollars
Population
5,400
Max Temp Winter
50ºF
Max Temp Summer
80ºF
Top Sights
Wildlife Safari, HillCrest Winery and Distillery and Spangler Vineyards

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Frequently asked questions

How much does a Winston vacation package cost?
Offering excellent value package deals from $404 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?
You can usually find lower prices and better availability in January, August and December. Take a look at our cheap Winston vacation packages and you could get some great off-season discounts.
How many days is enough for Winston?
With a well-organized itinerary, you can easily tick off the most popular Winston sights in a few days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your Winston vacation for longer.
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. Pick your travel dates: The things you want to do in Winston and your preferred season will help you decide when to travel.
  2. Set your budget: Factor in costs such as flights, food and transportation when working out how much to put aside for your trip to Winston. Then, choose a hotel that suits your budget, whether that's a low-cost stay or a swankier retreat.
  3. Use Expedia's trip planning tool to discover Winston: Research every part of your trip to Winston with this comprehensive planner. Invite your friends and family to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how long to go for: Now that you're up to speed on Winston, you can figure out the right length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Winston vacation package that brings all your bookings together.
  6. Add on excursions and experiences: Have a look at our travel guide to find some incredible things to do in Winston in Winston. Book tickets or make reservations as soon as you can to save time and avoid the hassle of searching for activities once you arrive.

Does Expedia offer Book Now, Pay Later Winston vacation packages?
Set off on your ideal getaway to Winston with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until payday --- we've partnered with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stick to your budget and snag great deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.