Winston Vacations from $565

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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.
Siltcoos Station Retreats

Siltcoos Station Retreats

4 out of 5
Price was $629, price is now $565 per person
$565
per person
Jul 31 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to North Bend (OTH)
9.2/10 Wonderful! (9 reviews)
While we didn't think this would be like a room at the Holiday Inn, we weren't prepared for the cute little room we got. The rooms are what used to be a RR station and have been upfitted with enough modern conveniences that you won't be disappointed - surprised, but not disappointed. Our room (and I assume the others are like this) was filled with gadgets, devices, and appliances that were vintage for the time the RR was operating and stopped there (think early 1900's). It was fun to try and figure out what these items were used for back in the day. They have WiFi, a refrigerator, a stove, and a microwave so you're not back in the 1900's yourself. It's an interesting mix of eclectic, nostalgic, and quaint. Very nice!

Reviewed on Jun 25, 2026

Motel 6 Gold Beach, OR

Motel 6 Gold Beach, OR

2 out of 5
Price was $917, price is now $776 per person
$776
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to North Bend (OTH)
7.6/10 Good! (11 reviews)
Shower water was nice and hot with plenty of pressure. Sink water faucet was either off or on full blast getting you soaked.

Reviewed on Jun 19, 2026

Bay Point Landing

Bay Point Landing

3.5 out of 5
Price was $1,662, price is now $1,442 per person
$1,442
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to North Bend (OTH)
9.2/10 Wonderful! (330 reviews)
Beautiful and breathtaking so relaxing! I will be taking my family back this summer. The sunrise and sunset photo shoots were unmatched.

Reviewed on May 8, 2026

The Wildflower Inn

The Wildflower Inn

2 out of 5
Price was $712, price is now $638 per person
$638
per person
Aug 4 - Aug 7
found 21 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to North Bend (OTH)
9.8/10 Exceptional! (219 reviews)
Very nice and clean property. The room was nice and check in was easy. Shower and tub was great!

Reviewed on Jun 24, 2026

Global INN

Global INN

3 out of 5
Price was $810, price is now $734 per person
$734
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to North Bend (OTH)
6.6/10 (1,010 reviews)
Staff was very friendly and helpful. I had trouble turning on tv with remote. Staff came and helped. Could not lower volume so had to mute. Hotel was a Super 8 before. That was access for Internet. Furniture was worn down but usable. Mold on caulking. I feel they tried to fix up/repair the hotel.

Reviewed on Jun 26, 2026

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Stay near popular Winston attractions

Wildlife Safari

9.2/5 (181 reviews)
Drive through 600 acres where lions, giraffes, and rhinos roam freely in natural habitats. Wildlife Safari's renowned cheetah breeding program has produced over 230 cubs for global conservation efforts.
See properties

Winston Hotel Deals

Safari Inn

Safari Inn

2 out of 5
101 NE Main Street Winston OR
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $98 total per night from Jul 8 to Jul 9
$98 total
Jul 8 - Jul 9
Total with taxes and fees
7.6/10 Good! (379 reviews)
"Owner Rick manages his SAFARI INN (Exit 119 off Interstate I-5) exceptionally well. I was a solo elderly female traveler on a budget looking for safe, clean, non-smoking, comfortable lodging for the two days I would be visiting the famous 53-year-old, 680-acre Wildlife Safari conservation & rare ..."

Reviewed on Jun 20, 2026

Safari Inn
The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston OR
$357 nightly
The price is $387 total per night from Jul 6 to Jul 7
$387 total
Jul 6 - Jul 7
Total with taxes and fees
The Watusi Place - A Modern Umpqua Valley Getaway
Family-Friendly Winston Vacation Rental w/ Deck!

Family-Friendly Winston Vacation Rental w/ Deck!

Winston OR
10/10 Exceptional! (19 reviews)
"The house was very nice for our purposes. My 4 year old son found the kids room and all the books and games to be an awesome treat. The house was very well appointed, we had everything we needed to cook, clean and have fun. If you're looking to be close to the wildlife safari, it's less than 10 minutes ..."

Reviewed on Sep 12, 2025

Get rates
Family-Friendly Winston Vacation Rental w/ Deck!
See all 109 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 $565 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.

Explore a world of travel with Expedia

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