
Winston Vacations from $470
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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.
The Latest Winston vacation packages
Price found within the past 48 hours. Click for updated prices.

Wild Rivers Motor Lodge
Price was $518, price is now $470 per person
$470
per person
Jan 15 - Jan 18
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to North Bend (OTH)
7.8/10 Good! (499 reviews)
Stayed at this property for three nights late October, I chose it because it’s pet friendly. While the room was clean and the beds comfortable, I couldn’t use the coffee maker or the refrigerator. The coffee maker would not filter water through to make a full cup of coffee, and when I asked if there was an extra in one of the many unused rooms, I was told no, there wasn’t another available. The refrigerator froze Everything I put in it the first day and after turning it almost all the way off I decided to give up and get ice in my cooler. In addition, it took 3 to 5 minutes of fiddling with the key in the door knob every time I wanted to get back in my room. When I asked at the office why this was I was told when it gets cold the door knobs all do it and the owner did not want to replace the door knobs. Come on, probably about $20 a door knob to replace! Oh, and don’t mind the guy camping out in the parking lot!. I think there may be better places to stay in Brookings.
Reviewed on Nov 1, 2026

Siltcoos Station Retreats
Price was $967, price is now $724 per person
$724
per person
Jan 15 - Jan 18
found 14 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to North Bend (OTH)
9.4/10 Exceptional! (12 reviews)
Out of all of the places we stayed on our trip driving up the coast, this was by far our favorite stop. We stayed at fancy resorts and swanky hotels, but the Siltcoos retreat was just magical! The amount of detail everywhere you look was amazing. The time and effort put into our conductors cabin, had us in awe. You guys are legendary for what you’ve accomplished there. Y’all we had deer walk up to us in the back yard! They didn’t even care we were there! The next time we are in Oregon, we will be staying with you! Thank you again for a magical stay. Your creativity has inspired us! I also thought it was funny you had “Du Monde” coffee because my maiden name is Dumond. So cool!
Reviewed on Sep 16, 2026

The Star Trek - USS Enterprise Room at the Itty Bitty Inn
Price was $702, price is now $613 per person
$613
per person
Jan 15 - Jan 18
found 14 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to North Bend (OTH)
10/10 Exceptional! (53 reviews)
Super fun place w/ lots of personal little Star Trek features. Owner was friendly and helpful. Wish I could have stayed longer!
Reviewed on Oct 7, 2026

The Florentine Waterfront Hotel
Price was $706, price is now $624 per person
$624
per person
Jan 15 - Jan 18
found 14 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to North Bend (OTH)
9.6/10 Exceptional! (97 reviews)
This hotel is truly a hidden gem. It's a series of cabins that sit right on the water of Siltcoos Lake. My cabin was impeccably clean and so comfortable. I spent hours just sitting on the sofa looking out over the lake. It's in a very peaceful and serene location, so no street or city noise to mar the view. I had a very well-appointed kitchenette. The bed itself was probably one of the most comfortable hotel bed I've ever had. The bedding was luxurious and kept me warm all night (a feat in and of itself). The shower was really nice and hot. I internet was completely consistent. I truly enjoyed my stay and cannot recommend this place high enough. If I could give it ten stars, I would. I'll definitely be back.
Reviewed on Nov 2, 2026

Stay near popular Winston attractions
Winston Hotel Deals

The Watusi Place - A Modern Umpqua Valley Getaway
Winston OR
$339 nightly
The price is $368 total per night from Nov 6 to Nov 7
$368 total
Nov 6 - Nov 7
Total with taxes and fees
10/10 Exceptional! (60 reviews)
"It was a great place to stay while visiting for a family wedding."
Reviewed on Sep 29, 2026

Safari Inn
101 NE Main Street Winston OR
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $71 total per night from Nov 4 to Nov 5
$71 total
Nov 4 - Nov 5
Total with taxes and fees
7.6/10 Good! (384 reviews)
"Easy check in. Delightful safari theme. Clean rooms. Ample parking. Everything we needed at a great value."
Reviewed on Sep 28, 2026

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Winston OR
9.6/10 Exceptional! (67 reviews)
"We were in town for our son's wedding and had several people staying with us. The house had plenty of room to spread out and the kitchen and main area were a great place to gather for our Friday night dinner. Overall, we had a wonderful stay in this home."
Reviewed on Oct 13, 2026
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.
Find the Best Winston Vacation Packages
Winston Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 5,400 |
Max Temp Winter | 50ºF |
Max Temp Summer | 80ºF |
Top Sights | Wildlife Safari, HillCrest Winery and Distillery and Spangler Vineyards |
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- Wildlife Safari
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