Winston Vacation Packages

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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.

Things to do near Winston

Winston, Oregon, is perfect for outdoor enthusiasts and families seeking adventure. Visitors can enjoy a variety of activities, including golf vacations, wildlife safaris, and outdoor adventures. The area features a resort, recreational areas, and an amusement park, making it an ideal destination for a memorable vacation. Explore the scenic beauty and engaging experiences that Winston has to offer for a fantastic getaway.

Shopping

Winston offers charming local shops like the Winston Antique Mall for unique finds and gifts. If you're up for a drive, visit the nearby Town Centre in Roseburg for a wider selection of stores and shopping experiences.

Recreation

Experience the Umpqua Golf Resort for a challenging round of golf amid scenic landscapes, perfect for outdoor enthusiasts. For relaxation, head to Stanton Park, where you can unwind in serene surroundings, or play at Cougar Canyon Golf Course, which offers a stunning natural setting for sports lovers.

Adventure

The Umpqua Valley Tennis Center, located 11.3km from Winston, provides a vibrant atmosphere for tennis enthusiasts. Enjoy friendly matches and improve your skills while soaking in the beautiful surroundings. It's an ideal spot for both recreational play and competitive spirit, perfect for an adventurous outing.

Nightlife

Winston, Oregon, offers a cozy nightlife with local pubs like the 7 Feathers Casino Resort, featuring gaming and live entertainment. Enjoy a laid-back evening at nearby bars, where friendly locals gather for drinks, music, and a welcoming atmosphere that captures the charm of small-town Oregon.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Winston

Winston, Oregon, is perfect for outdoor enthusiasts and families, offering stunning scenery and cultural experiences. Popular attractions include the scenic river, urban parks, and history museums, making it an ideal destination for those seeking adventure and family fun. For a comfortable stay, consider exploring Charlotte vacation rentals to enhance your visit. Enjoy all that Winston has to offer.

  • South Umpqua River: Only 1.1km away from Winston, the South Umpqua River offers breathtaking scenery and a serene outdoor atmosphere. Perfect for fishing, kayaking, or simply enjoying a leisurely stroll along the banks, this river is a haven for nature lovers and those seeking tranquility.
  • Douglas County Museum of History and Natural History: Located 9.7km from Winston, this museum immerses you in the rich culture and history of the region. With exhibits showcasing local artefacts and natural history, it’s an educational experience that highlights the unique heritage of Douglas County.
  • Stewart Park: Situated 11.3km from Winston, Stewart Park is a vibrant urban park ideal for families. With playgrounds, picnic areas, and walking trails, it provides a perfect setting for outdoor activities amidst the city's charm.

Best time to go to Winston

The best time to visit Winston can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winston falls in August, when visitor numbers are average and weather is sunny with no rain. The coolest average temperature in Winston falls in December, visitor numbers are moderately low and weather is mostly with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.3°F (4.6°C)Light RainMostlyAverageSlightly Low
February40.3°F (4.6°C)Light RainMostlyAverageSlightly Low
March42.6°F (5.9°C)Light RainMostlyModerately HighAverage
April46.6°F (8.1°C)Light RainMostlyAverageAverage
May52.5°F (11.4°C)Light RainMostly SunnyAverageAverage
June58.3°F (14.6°C)No RainMostly SunnyModerately HighSlightly High
July64.4°F (18.0°C)No RainMostly SunnyModerately HighSlightly High
August64.9°F (18.3°C)No RainSunnyAverageSlightly High
September60.1°F (15.6°C)No RainMostly SunnyAverageAverage
October52.0°F (11.1°C)Light RainMostly SunnyModerately LowAverage
November43.7°F (6.5°C)Light RainMostlyModerately LowAverage
December38.7°F (3.7°C)Light RainMostlyModerately LowSlightly Low

Tips to save on your trip to Winston

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Winston during the low season (December to February) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Ready to book your vacation to Winston?

 

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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 CA $97 per night from Aug 4 to Aug 5
CA $97
CA $105 total
Aug 4 - Aug 5
includes taxes & fees
7.6/10 Good! (354 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
The price is CA $199 per night from Aug 13 to Aug 14
CA $199
CA $503 total
Aug 13 - Aug 14
includes taxes & fees
10/10 Exceptional! (39 reviews)
"We stayed for three days and two nights. The house was incredibly clean and spacious. The bedrooms are neatly organized and there are lots of board games, and even outdoor connect 4 and corn hole. Would absolutely recommend this home and host."

Reviewed on Jul. 11, 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

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
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.

What to do in Winston

Frequently asked questions

How much does a Winston vacation package cost?
You'll find cheap prices on Expedia for your Winston escape. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Winston costs.
What are the cheapest months to go to Winston?
The off-season is the best time to visit Winston if you're hoping to keep costs down. Another tip for scoring cheap Winston vacation packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Winston?
The ideal length of your Winston vacation depends on what you'd like to do and see. Typically, a few days to a week will give you enough time to go to all the top sights and discover some hidden gems along the way.
How to find the best Winston package deals?
Use Expedia's handy filters to help you find some great Winston package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Winston package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Winston vacation as a package?
You can enjoy significant savings on your Winston break by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to see the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winston?
If you have your Winston travel dates confirmed, book early to snap up some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Winston?

  1. Choose when to travel: Check your diary and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Winston.
  2. Calculate your budget: Ensure you have enough money to pay for everything from meals and transportation to activities and flights. Your hotel will likely be the largest expense during your trip to Winston.
  3. Decide your trip length: Consider how much time you'd like to spend discovering Winston. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the ideal Winston vacation package for you.

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