Title: Winston Vacation Packages & Trips 2026 from CA $824 | Expedia.ca [Hotels in Winston](https://expedia.ca/Winston-Hotels.d6124402.Travel-Guide-Hotels)[Vacation Rentals in Winston](https://expedia.ca/Winston-Vacation-Rentals.d6124402.Travel-Guide-VacationRentals)[Flights to Winston](https://expedia.ca/Cheap-Flights-To-Winston.d6124402.Travel-Guide-Flights)[Things to do in Winston](https://expedia.ca/Things-To-Do-In-Winston.d6124402.Travel-Guide-Activities)[Winston Car Rentals](https://expedia.ca/Car-Rentals-In-Winston.d6124402.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6090413/6a7f406c-e7ef-4707-844b-63d5d9268f55.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winston Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Michelle Finseth - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Wildlife-Safari-Winston.d6090413.Vacation-Attraction), [South Umpqua River](https://www.expedia.ca/South-Umpqua-River-Oregon.d684502648556560384.Vacation-Attraction) and [Douglas County Museum of History and Natural History](https://www.expedia.ca/Douglas-County-Museum-Of-History-And-Natural-History-Roseburg.d553248621532642241.Vacation-Attraction) 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. ![Global INN](https://images.trvl-media.com/lodging/2000000/1530000/1522300/1522219/915bed23_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Global INN CA $824 per person Apr 4 - Apr 8 just found Roundtrip non-stop flight included Calgary (YYC) to North Bend (OTH) 6.4/10 (1,003 reviews) Parking is Safe and Convenient. Staff are on duty 24hrs and always ready to accomodate travelers needs. Reviewed on Jan 4, 2026 ![Red Lion Hotel Coos Bay](https://images.trvl-media.com/lodging/1000000/30000/20800/20750/fb588b2e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Red Lion Hotel Coos Bay CA $953 per person Apr 4 - Apr 8 just found Roundtrip non-stop flight included Calgary (YYC) to North Bend (OTH) 6.6/10 (1,001 reviews) Staff were friendly and helpful. Rooms are outdated but clean Reviewed on Jan 5, 2026 ![Bay Point Landing](https://images.trvl-media.com/lodging/52000000/51830000/51822800/51822739/a4828946_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bay Point Landing CA $1,238 per person Apr 1 - Apr 5 found 1 day ago Roundtrip flight included Montreal (YUL) to North Bend (OTH) 9.2/10 Wonderful! (277 reviews) Perfect stay! My husband and I stayed for two days and it was a great little get away! Wonderful views, quiet and peaceful, and many other amenities that we did not have chance to use. The cabin came equipped with everything we needed. Make sure you book a waterfront or water view, these are the most private cabins. Reviewed on Jan 5, 2026 ![Bandon Inn](https://images.trvl-media.com/lodging/71000000/70570000/70564000/70563988/98b61ca7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bandon Inn CA $1,280 per person Apr 1 - Apr 5 found 1 day ago Roundtrip flight included Montreal (YUL) to North Bend (OTH) 9.4/10 Exceptional! (1,303 reviews) Nice view, could see the lighthouse in the distance. Room was nice, and clean Reviewed on Jan 11, 2026 ![Gold Beach Inn](https://images.trvl-media.com/lodging/12000000/11570000/11564600/11564540/40f81479_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Gold Beach Inn CA $838 per person Apr 4 - Apr 8 just found Roundtrip non-stop flight included Calgary (YYC) to North Bend (OTH) 7/10 Good! (1,001 reviews) Our room was pretty clean and didn’t smell bad at all and was updated and modern from the looks of it. The bed however was extremely firm and could definitely use a pillowtopper for people who can’t sleep with very hard surfaces we got the king ocean view room and the view was nice and listening to the ocean was great at the evening hours from the deck as it was only about 150 yards away or so . We were however disappointed that the spa and hot tubs were closed as it was one of the main reasons we chose the inn and it was not shown as closed on the website or on Expedia but for the price which was very reasonable we just had to get over it . I would say the free breakfast was not all good the mini fruit filled pastries were stale but they did have good quality tea/coffee and yogurt and fruit available as well as waffle making supplies we chose the yogurt and fruit as that’s what we like . But overall very decent room and we would stay again I would ask that they advertise the spa and hot tub areas being open or closed and the times and dates so people would know prior to booking. We Would definitely have given it a 5 stars if the bed was a bit newer or at least more comfortable and had access to the hot tubs . Reviewed on Dec 16, 2025 ### 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. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 40.3°F (4.6°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | February | 40.3°F (4.6°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | March | 42.6°F (5.9°C) | Light Rain | Mostly Cloudy | Moderately High | Average | | April | 46.6°F (8.1°C) | Light Rain | Mostly Cloudy | 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 Cloudy | Moderately Low | Average | | December | 38.7°F (3.7°C) | Light Rain | Mostly Cloudy | 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 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? Choose your dates ## Winston Hotel Deals ![Safari Inn](https://images.trvl-media.com/lodging/9000000/8780000/8777200/8777128/416cc059_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Safari Inn 101 NE Main Street Winston OR Fully refundableReserve now, pay when you stay CA $83 CA $91 total Jan 12 - Jan 13 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 [](https://expedia.ca/Hotel-Search?startDate=12%2F01%2F2026&endDate=13%2F01%2F2026&selected=8777128&PinnedHotelID=8777128&HadPinnedHotel=true®ionId=6124402) ![The Watusi Place - A Modern Umpqua Valley Getaway](https://images.trvl-media.com/lodging/79000000/78310000/78301400/78301309/f90085c8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Watusi Place - A Modern Umpqua Valley Getaway Winston OR CA $207 CA $506 total Jan 14 - Jan 15 includes taxes & 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 [](https://expedia.ca/Hotel-Search?startDate=14%2F01%2F2026&endDate=15%2F01%2F2026&selected=78301309&PinnedHotelID=78301309&HadPinnedHotel=true®ionId=6124402) ![Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen ](https://images.trvl-media.com/lodging/41000000/40010000/40002000/40001956/3a3f8494_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=40001956&PinnedHotelID=40001956&HadPinnedHotel=true®ionId=6124402) [](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=40001956&PinnedHotelID=40001956&HadPinnedHotel=true®ionId=6124402) [See all 113 properties in Winston](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F01%2F2026&endDate=13%2F01%2F2026®ionId=6124402) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### What to do in Winston ![4 Day Ngorongoro Crater Tarangire and Serengeti National Park](https://mediaim.expedia.com/localexpert/46108407/0fc7c751-4c8b-4be7-86d3-c7b258f60550.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 4 Day Ngorongoro Crater Tarangire and Serengeti National Park CA $1,229 per adult [](https://expedia.ca/things-to-do/4-day-ngorongoro-crater-tarangire-and-serengeti-national-park.a46108407.activity-details) [See all activities in Winston](https://expedia.ca/things-to-do/search?rid=6124402) ## Explore a world of travel with Expedia - 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