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.

Top Winston Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Anchor Bay Inn
Bandon Marina Inn
The Wildflower Inn
Red Lion Hotel Coos Bay
Bay Point Landing

Things to do near Winston

Winston, Oregon, is an ideal destination for outdoor enthusiasts and families seeking a scenic getaway. Enjoy various activities such as golfing, wildlife safaris, and outdoor adventures. The town features a resort, recreational areas, and an arena entertainment facility, ensuring a memorable vacation experience. Whether you're looking for relaxing trips or exciting excursions, Winston has something to offer for everyone.

Shopping

Winston offers unique shopping experiences at local boutiques and gift shops. If you're up for a drive, head to the nearby Valley River Center, about 24.1km away, where you'll find a variety of retail stores and dining options for a full day of shopping.

Recreation

Enjoy a round of golf at Cougar Canyon Golf Course, where you can embrace the outdoor vibes while honing your skills. For a tranquil experience, visit Stanton Park or Herbert's Pond Park, both offering serene environments perfect for relaxation and rejuvenation.

Adventure

Experience the Umpqua Valley Tennis Center, located 11.3km from Winston. Enjoy a vibrant atmosphere while playing tennis surrounded by scenic views. It's an excellent spot for both enthusiasts and casual players, perfect for honing your skills or enjoying a friendly match.

Nightlife

Winston, Oregon offers a relaxed nightlife with cozy bars and live music venues. Check out local spots where you can enjoy craft beers and engage with friendly locals. The atmosphere is welcoming, perfect for unwinding after a day of exploring the beautiful surroundings.

*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 an ideal destination for outdoor enthusiasts and families, offering scenic views and cultural experiences. Visitors can explore attractions like the beautiful river, urban parks, and history museums, all designed to cater to various interests. For those planning a stay, consider searching for Charlotte vacation rentals to enhance your trip. With its blend of nature and family-friendly activities, Winston promises an enjoyable getaway for all travellers.

  • South Umpqua River: A serene spot located 1.1km from Winston, the South Umpqua River offers stunning scenery and a perfect outdoor vibe. Whether you're kayaking, fishing, or simply enjoying a leisurely walk along the banks, this river is ideal for nature enthusiasts.
  • Douglas County Museum of History and Natural History: Situated 9.7km away, this museum showcases the rich cultural heritage of the region. Explore fascinating exhibits that delve into local history and natural history, providing an enriching experience for all visitors.
  • Stewart Park: Just 11.3km from Winston, Stewart Park is a family-friendly urban park that combines outdoor fun with city vibes. Enjoy picnicking, walking trails, or playing in the playgrounds, making it a wonderful spot for families to unwind.

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 cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.3°F (4.6°C)Light RainMostly CloudyAverageSlightly Low
February40.3°F (4.6°C)Light RainMostly CloudyAverageSlightly Low
March42.6°F (5.9°C)Light RainMostly CloudyModerately HighAverage
April46.6°F (8.1°C)Light RainMostly CloudyAverageAverage
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 RainMostly CloudyModerately LowAverage
December38.7°F (3.7°C)Light RainMostly CloudyModerately 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 during the off-peak season (typically December to February) for more affordable package holidays to Winston.
  • 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 $82 per night from Feb 20 to Feb 21
CA $82
CA $89 total
Feb 20 - Feb 21
includes taxes & fees
7.6/10 Good! (372 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
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

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston OR
The price is CA $203 per night from Feb 10 to Feb 11
CA $203
CA $504 total
Feb 10 - Feb 11
includes taxes & fees
10/10 Exceptional! (48 reviews)
Everything was great!

Reviewed on Jan 3, 2026

The Watusi Place - A Modern Umpqua Valley Getaway
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

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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.