Winston Vacations from $870
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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, 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.
Siltcoos Station Retreats
$1,168
per person
Dec 24 - Dec 27
found 18 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 Florentine Waterfront Hotel
$1,349
per person
Dec 24 - Dec 27
found 18 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to North Bend (OTH)
9.6/10 Exceptional! (97 reviews)
Really enjoyed our stay here. As unassuming the outside might be the cabin was VERY well appointed and very comfortable! Very well done!! Staff friendly and accommodating as well. A MUST STAY!!
Reviewed on Oct 22, 2026
The Star Trek - USS Enterprise Room at the Itty Bitty Inn
$907
per person
Dec 31 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to North Bend (OTH)
10/10 Exceptional! (52 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
Stay near popular Winston attractions
Wildlife Safari
9.2/10 (181 reviews)
Drive through 600 acres where lions, giraffes, and rhinos roam freely in natural habitats. Wildlife Safari's renowned cheetah breeding program has produced over 230 cubs for global conservation efforts.
Abacela Winery
8.8/10 (15 reviews)
Pioneering Spanish grape varieties in Oregon since 1995, Abacela Winery showcases the Umpqua Valley's unique terroir. Enjoy seated tastings on the vineyard-view patio paired with artisanal cheese and charcuterie.
Winston Hotel Deals
The Watusi Place - A Modern Umpqua Valley Getaway
Winston OR
$353 nightly
$383 total
Oct 27 - Oct 28
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
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
Family-Friendly Winston Vacation Rental w/ Deck!
Winston OR
10/10 Exceptional! (22 reviews)
"Wonderful place well stocked with more then what we needed and it was charming, clean, and cool inside, gorgeous outside! Host was excellent as well easy to contact!"
Reviewed on Jul 16, 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 |
More vacations you might like
Frequently asked questions
How much does a Winston vacation package cost?
Offering excellent value package deals from $870 on Expedia, you'll be thrilled with how little a vacation to Winston costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Winston?
You can usually find lower prices and better availability in January, August and December. Take a look at our cheap Winston vacation packages and you could get some great off-season discounts.
How many days is enough for Winston?
With a well-organized itinerary, you can easily tick off the most popular Winston sights in a few days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your Winston vacation for longer.
How to find the best Winston package deals?
Landing a cheap Winston package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply some filters and see what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most affordable Winston package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winston vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights individually. Better still, you can tailor your Winston escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Winston?
Enjoy fantastic discounts by booking your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Winston escape.
How to plan a trip to Winston?
- Pick your travel dates: The things you want to do in Winston and your preferred season will help you decide when to travel.
- Set your budget: Factor in costs such as flights, food and transportation when working out how much to put aside for your trip to Winston. Then, choose a hotel that suits your budget, whether that's a low-cost stay or a swankier retreat.
- Use Expedia's trip planning tool to discover Winston: Research every part of your trip to Winston with this comprehensive planner. Invite your friends and family to collaborate on a group trip, search for stays or things to do and make bookings.
- Decide how long to go for: Now that you're up to speed on Winston, you can figure out the right length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Winston vacation package that brings all your bookings together.
- Add on excursions and experiences: Have a look at our travel guide to find some incredible things to do in Winston in Winston. Book tickets or make reservations as soon as you can to save time and avoid the hassle of searching for activities once you arrive.
Does Expedia offer Book Now, Pay Later Winston vacation packages?
Set off on your ideal getaway to Winston with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until payday — we've partnered with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stick to your budget and snag great deals while they last.
Explore a world of travel with Expedia
- B&B in Roseburg
- Cheap Hotels in Winston
- Cabin Rentals in Winston
- Luxury Hotels in Roseburg
- Motels in Dillard
- Grants Pass Hotels
- Best Western Hotels in Roseburg
- Myrtle Creek Hotels
- Treehouses in Winston
- Hotels on the River in Roseburg
- Hotels near Seven Feathers Casino
- Winston Hotels
- Extended Stay Hotels in Roseburg
- Romantic Hotels in Roseburg
- Apartments in Roseburg
- Family Hotels in Winston
- Coos Bay Hotels
- Best Western Hotels in Winston
- Green Hotels
- Vacation Homes in Green
- 5 Star Hotels in Winston
- Pet-Friendly Hotels in Roseburg
- Hotels near South Umpqua River
- Hotels with smoking rooms in Winston
- Hotels near Abacela Winery
- Gay friendly Hotels in Roseburg
- Roseburg Hotels
- Casino Hotels in Roseburg
- Hotels near Douglas County Museum of History and Natural History
- B&B in Winston
- Hotels near Wildlife Safari
- Motels in Winston
- Hotels near Stewart Park
- Cheap Hotels in Roseburg
- Dillard Hotels
- Hotels with an Indoor Pool in Roseburg
- Hotels with Bars in Roseburg
- Motels in Roseburg
- La Quinta Inn & Suites Hotels in Roseburg
- Resorts & Hotels with Spas in Roseburg
- 3 Star Hotels in Roseburg
- Hotels with Hot Tubs in Roseburg
- Hotels with Restaurants in Roseburg
- Cabin Rentals in Green
- Cabin Rentals in Roseburg
- Rv Parks in Roseburg
- Flights from Medford (MFR) to Roseburg (RBG)
- Flights from Portland (PDX) to Roseburg (RBG)
- Flights to Winston
- Flights to Roseburg
- Flights from Seattle (SEA) to Roseburg (RBG)
- Flights from Roseburg
- Flights from Salem (SLE) to Roseburg (RBG)
- Flights from Winston
- Flights from Phoenix (PHX) to Roseburg (RBG)
- Flights from Eugene (EUG) to Roseburg (RBG)
- Flights from Roseburg Regional
- Wildlife Safari
- Melrose Vineyards
- Umpqua National Forest
- Visit Roseburg
- Applegate Trail Interpretive Center
- North Umpqua River
- Pony Village Mall
- Reustle Prayer Rock Vineyards
- The Mill Casino
- Coos Bay Vacations
- River's Edge Winery
- Wolf Creek Vacations
- Rice Hill Vacations
- Oakland Vacations
- Grave Creek Bridge
- Seven Feathers Casino
- Toketee Falls
- Douglas County Museum of History and Natural History
- Glaser Estate Winery & Distillery
- Visit Winston
- Hillcrest Winery and Distillery
- Abacela Winery
- Coos Bay Boardwalk
- Leland Vacations
- Charleston Vacations
- Roseburg Vacations
- Myrtle Point Vacations
- Bandon Beach
- Spangler Vineyards
- Sutherlin Vacations
- Girardet Wine Cellars
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
