Winston Vacations from $521

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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.
Jot's Resort

Jot's Resort

2.5 out of 5
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Boise (BOI) to North Bend (OTH)
8.8/10 Excellent! (1,866 reviews)
large number of rooms. quiet and pleasant view of river

Reviewed on Jul 18, 2025

Bandon Marina Inn

Bandon Marina Inn

2 out of 5
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to North Bend (OTH)
8.8/10 Excellent! (181 reviews)
Thank you for everything

Reviewed on Jul 9, 2025

Beachfront Inn

Beachfront Inn

2.5 out of 5
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Boise (BOI) to North Bend (OTH)
9/10 Wonderful! (1,005 reviews)
The location is great, right on the ocean. The room was fine, no complaints except there is no AC and the ocean is loud when the doors are open. The pool and hot tub should have been refinished long ago so we didn’t use either. The breakfast offers little or nothing for diabetic or health conscious people. Overall average in great location.

Reviewed on Jul 15, 2025

Bandon Inn

Bandon Inn

3 out of 5
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Boise (BOI) to North Bend (OTH)
9.4/10 Exceptional! (1,204 reviews)
This is a real gem on the Oregon coast

Reviewed on Jul 16, 2025

Castillo di Sabbia

Castillo di Sabbia

2 out of 5
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Boise (BOI) to North Bend (OTH)
No reviews
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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

Winston Hotel Deals

Safari Inn

Safari Inn

2 out of 5
101 NE Main Street, Winston, OR
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $81 total per night from Jul 21 to Jul 22
$81 total
Jul 21 - Jul 22
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
$318 nightly
The price is $345 total per night from Jul 21 to Jul 22
$345 total
Jul 21 - Jul 22
Total includes taxes and fees
10/10 Exceptional! (38 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
9.6/10 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 Jun 25, 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 $521 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.