Winston Vacations from $512

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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.
Motel 6 Coos Bay, OR

Motel 6 Coos Bay, OR

2 out of 5
Price was $560, price is now $512 per person
$512
per person
Jan 23 - Jan 25
found 11 hours ago
Roundtrip flight included
Houston (HOU) to North Bend (OTH)
6.8/10 (1,024 reviews)
Yes, nice room same as pictures I encountered difficulties trying to book two consecutive nights and the staff were very helpful in merging my two separate booking into a seamless stay. My girlfriend enjoys doing our laundry while we're guests as its affordable and coinless

Reviewed on Nov 29, 2025

The Star Trek - USS Enterprise Room at the Itty Bitty Inn

The Star Trek - USS Enterprise Room at the Itty Bitty Inn

2 out of 5
Price was $720, price is now $633 per person
$633
per person
Jan 23 - Jan 25
found 11 hours ago
Roundtrip flight included
Houston (HOU) to North Bend (OTH)
10/10 Exceptional! (42 reviews)
WOW! Each was accurately themed. Inn owner was gracious. I am so glad we stayed.

Reviewed on Oct 13, 2025

Bay Point Landing

Bay Point Landing

3.5 out of 5
Price was $706, price is now $642 per person
$642
per person
Jan 23 - Jan 25
found 11 hours ago
Roundtrip flight included
Houston (HOU) to North Bend (OTH)
9.2/10 Wonderful! (277 reviews)
Such a great environment! Can’t wait to go back.

Reviewed on Nov 26, 2025

Best Western Inn At Face Rock

Best Western Inn At Face Rock

3 out of 5
Price was $656, price is now $600 per person
$600
per person
Jan 23 - Jan 25
found 11 hours ago
Roundtrip flight included
Houston (HOU) to North Bend (OTH)
9.2/10 Wonderful! (1,000 reviews)
my wife and I had a wonderful experience. When we checked in Donna and Tessa were super fun, we were joking around and had a great time. We need more people like this in these positions made our experience wonderful

Reviewed on Nov 16, 2025

Edgewater Inn and Suites, an Ascend Collection Hotel

Edgewater Inn and Suites, an Ascend Collection Hotel

2 out of 5
Price was $604, price is now $557 per person
$557
per person
Jan 23 - Jan 25
found 11 hours ago
Roundtrip flight included
Houston (HOU) to North Bend (OTH)
8.4/10 Very Good! (1,246 reviews)
Clean room. Wonderful pool

Reviewed on Nov 24, 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

Winston Hotel Deals

Safari Inn

Safari Inn

2 out of 5
101 NE Main Street Winston OR
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $71 total per night from Dec 1 to Dec 2
$71 total
Dec 1 - Dec 2
Total with taxes and fees
7.6/10 Good! (370 reviews)
Was just ok. One spontaneous night stay. Read the fine print on this property. They require a 100 $ cash deposit upon check in. He said it was just in case we smoked in the room. I guess that happens at a lower grade MOTEL. He was nice enough about it tho. Room seemed clean no funky smells. Would ...

Reviewed on Nov 12, 2025

Safari Inn
The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston OR
$330 nightly
The price is $358 total per night from Nov 30 to Dec 1
$358 total
Nov 30 - Dec 1
Total with taxes and fees
10/10 Exceptional! (47 reviews)
Home was well stocked and was very accessible to our winery we belong to.

Reviewed on Nov 6, 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 OR
9.6/10 Exceptional! (60 reviews)
You walk into the great room when you check in and it is well designed. The area is spacious and the kitchen is very nice. Everything we needed was in the kitchen except the only large bowls available were plastic and it would have been nice to have metal or glass. Comfortable seating in the tv area. ...

Reviewed on Oct 5, 2025

Get rates
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
See all 112 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 $512 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.

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