Winston Vacation Packages & Trips 2025

Name: Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Address: Winston
Rating: 9.6

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	40.3°F (4.6°C)	Light Rain	Mostly	Average	Slightly Low
February	40.3°F (4.6°C)	Light Rain	Mostly	Average	Slightly Low
March	42.6°F (5.9°C)	Light Rain	Mostly	Moderately High	Average
April	46.6°F (8.1°C)	Light Rain	Mostly	Average	Average
May	52.5°F (11.4°C)	Light Rain	Mostly Sunny	Average	Average
June	58.3°F (14.6°C)	No Rain	Mostly Sunny	Moderately High	Slightly High
July	64.4°F (18.0°C)	No Rain	Mostly Sunny	Moderately High	Slightly High
August	64.9°F (18.3°C)	No Rain	Sunny	Average	Slightly High
September	60.1°F (15.6°C)	No Rain	Mostly Sunny	Average	Average
October	52.0°F (11.1°C)	Light Rain	Mostly Sunny	Moderately Low	Average
November	43.7°F (6.5°C)	Light Rain	Mostly	Moderately Low	Average
December	38.7°F (3.7°C)	Light Rain	Mostly	Moderately Low	Slightly 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?

Choose your dates

Winston Hotel Deals

Safari Inn

101 NE Main Street, Winston, OR

CA $97

CA $105 total

Sep 2 - Sep 3

includes taxes & fees

7.6/10 Good! (359 reviews)

Bang for my buck

"Great room for my budget. Needed a place to just sleep in during a long road trip. I was very pleased with the comfort and cleanliness of the room, as well as the amenities. Very happy!!"

Reviewed on Aug. 17, 2025

The Watusi Place - A Modern Umpqua Valley Getaway

Winston

CA $230

CA $538 total

Aug 24 - Aug 25

includes taxes & fees

10/10 Exceptional! (40 reviews)

"Such a cute house in a nice, quiet neighborhood! The layout was perfect for our family, with plenty of space to relax and feel at home. Leah truly thought of everything we might need—so thoughtful and well-stocked. Check-in and check-out were a breeze. We really enjoyed our stay!"

Reviewed on Aug. 1, 2025

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

See all 99 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.

What to do in Winston

4 Day Ngorongoro Crater Tarangire and Serengeti National Park

CA $1,232

per adult

See all activities 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?

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.
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.
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.
Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the ideal Winston vacation package for you.

Other vacations you might like

Portland Vacations

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

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Winston Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy