Book Exclusive Winston Vacation Packages
Winston flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Edgewater Inn and Suites, Ascend Hotel Collection
per person
Jul. 19 - Jul. 23
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to North Bend (OTH)
Stay at this motel in Coos Bay. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Coos Bay Boardwalk and Coos River are located nearby.
Bay Point Landing
per person
Jul. 19 - Jul. 23
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to North Bend (OTH)
Stay at this 3.5-star aparthotel in Coos Bay. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Coos Historical & Maritime Museum and Bastendorff Beach are located nearby.
Siltcoos Station Retreats
per person
Jul. 19 - Jul. 23
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to North Bend (OTH)
Stay at this 4-star aparthotel in Westlake. Enjoy free WiFi, free parking, and a marina. Popular attractions Siltcoos Lake and Jessie M. Honeyman State Park are located nearby.
Bandon Inn
per person
Jul. 19 - Jul. 23
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to North Bend (OTH)
Stay at this 3-star motel in Bandon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bandon Dunes Golf Resort and Pacific Blues are located nearby.
Beachfront Inn
per person
Jul. 19 - Jul. 23
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to North Bend (OTH)
Book a stay at this beach hotel in Brookings. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Sporthaven Beach and Pelican Bay Lighthouse are located nearby.
Top Winston hotels deals
Safari Inn
101 NE Main Street, Winston, OR
Free cancellation
Reserve now, pay when you stay
The price is CA $89 per night
CA $89
CA $97 total
includes taxes & fees
May 26 - May 27
Stay at this motel in Winston. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Wildlife Safari and South Umpqua River are located nearby.
Parking included
Free WiFi
The Watusi Place - A Modern Umpqua Valley Getaway
The price is CA $216 per night
CA $216
CA $517 total
includes taxes & fees
Jun 4 - Jun 5
Stay at this vacation home in Winston. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Wildlife Safari and Abacela Winery are located nearby.
Kitchen
Washer
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Stay at this vacation home in Winston. Enjoy free WiFi, a garden, and patios. Popular attractions Wildlife Safari and South Umpqua River are located nearby.
Kitchen
Washer
Family-Friendly Winston Vacation Rental w/ Deck!
Book a stay at this family-friendly vacation home in Winston. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Wildlife Safari and South Umpqua River are located nearby.
Kitchen
Washer
Family-friendly Winston Vacation Rental w/ Deck!
Stay at this 3-star cottage in Winston. Enjoy free parking and air conditioning. Popular attractions Wildlife Safari and South Umpqua River are located nearby.
Kitchen
Washer
Riverfront Inn Roseburg
315 W Harvard Ave, Roseburg, OR
Free cancellation
Reserve now, pay when you stay
The price is CA $156 per night
CA $156
CA $171 total
includes taxes & fees
May 25 - May 26
Stay at this motel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stewart Park and Douglas County Museum of History and Natural History are located nearby.
Pool
Breakfast included
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.
Popular places to visit
Wildlife Safari
5/5(2 reviews)
Why not see the exotic and native animals who live at Wildlife Safari during your vacation in Winston? While you're in the area, stroll along the riverfront.
Abacela Winery
You can enjoy a tasting or tour at Abacela Winery during your travels to Winston. While you're in the area, stroll along the riverfront.
Winston Vacations
If you were sick the day your geography teacher taught your class where Winston is situated, don't worry. With a little help from us, you'll find it in a flash!
You'll discover this Roseburg neighborhood 15 miles (24 kilometers) southwest of the downtown area.
There are 21,000 locals that call Roseburg home.
Places to visit in Winston
Snowboarding is a popular activity in Roseburg and a superb excuse to get out and discover more of this unique region. If you're really looking to create some unforgettable vacation memories, put skiing on your itinerary too.Where do you fly into for Winston?
If you're traveling to Winston, the closest terminal is Southwest Oregon Regional Airport (OTH). It's around 45 miles (72 kilometers) northwest from the central area. Select an in-flight movie, sit back and relax and you'll arrive in no time at all.Photos of local treasures
Browse Winston vacation photos for more inspiration
