A serene lake with a reflection of a forested mountain and a small house on the shore.

Winston Vacations from $513

Book a Hotel + Flight or Car together to unlock savings

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.
  • Dec 30 - Jan 3

    Hayward Inn + Flight

    East University
    4 nights
    3.0 star property
    9.0/10 - Wonderful (3,227 reviews)
    Roundtrip • San Francisco (SFO) - Eugene (EUG)
    SFO - EUG • Nonstop EUG - SFO • Nonstop
    $605
    $513
    per traveler
    found 1 day ago
    Hayward Inn
  • Dec 24 - Dec 30

    Motel 6 Madras, OR + Flight

    Madras
    6 nights
    2.0 star property
    8.0/10 - Very good (952 reviews)
    "Nice place! My second time here. Quiet. Well lit parking lot. Room layouts make you move everything around to watch the TV, but no biggie. I'll stay here again! But the hard plastic chairs HAVE TO GO!!!"
    Reviewed November 1, 2026
    Roundtrip • Los Angeles (LAX) - Redmond (RDM)
    LAX - RDM • Nonstop RDM - LAX • 1 stop
    $636
    $526
    per traveler
    found 1 hour ago
    Motel 6 Madras, OR
  • Dec 27 - Dec 30

    Juniper Preserve + Flight

    Pronghorn
    3 nights
    4.0 star property
    9.2/10 - Wonderful (750 reviews)
    "The fire pit was everything. The resort is beautiful, the staff is friendly, the beds are comfy. We will be returning. Everyone was so sweet to our puppy, Belladonna."
    Reviewed November 8, 2026
    Roundtrip • Denver (DEN) - Redmond (RDM)
    DEN - RDM • 1 stop RDM - DEN • 1 stop
    $779
    $658
    per traveler
    found 13 hours ago
    Juniper Preserve
  • Jan 5 - Jan 8

    River Bend Big Sky by Avantstay Private Riverfront Sauna + Game Room + Decks Near Mt. Bachelor + Flight

    Deschutes River Woods
    3 nights
    3.0 star property
    Roundtrip • Los Angeles (LAX) - Redmond (RDM)
    LAX - RDM • Nonstop RDM - LAX • Nonstop
    $1,491
    $1,268
    per traveler
    found 1 day ago
    River Bend Big Sky by Avantstay Private Riverfront Sauna + Game Room + Decks Near Mt. Bachelor
  • Jan 9 - Jan 12

    Yurtel-Veneta + Flight

    Veneta
    3 nights
    2.0 star property
    9.0/10 - Wonderful (4 reviews)
    "Overall we had a nice, cozy stay at the Yurtel. We needed to book last-minute accomodations for a football game in Eugene and this was a safe, affordable place to stay not absurdly far away. Our yurt was warm and comfortable and the water pressure in the shower was excellent. Our only complaint is the road and neighborhood noise. It should go without saying that you're going to hear outside noise if you're staying in a yurt, but the noise from the nearby highway was quite loud. We also could..."
    Reviewed November 2, 2026
    Roundtrip • Milwaukee (MKE) - Eugene (EUG)
    MKE - EUG • 1 stop EUG - MKE • 1 stop
    $829
    $711
    per traveler
    found 22 hours ago
    Yurtel-Veneta

Where to stay in and around Winston

Winston, Oregon offers a delightful mix of outdoor adventures and scenic beauty, perfect for family vacations. Explore downtown Winston's charming atmosphere, take a trip down Lookingglass Road, or venture to nearby Roseburg for more experiences. Enjoy the friendly vibes and budget-friendly options in this welcoming region.

Roseburg

Roseburg is the ultimate destination for travelers seeking outdoor adventures and family-friendly experiences. With attractions like Stewart Park and the Douglas County Museum of History and Natural History, visitors can immerse themselves in both recreation and local culture. The beautiful scenery surrounding Winchester Dam adds to the area's allure. Located about 7 miles by car from Winston, Roseburg offers easy access for those looking to explore Southern Oregon. Booking a stay here ensures a memorable getaway filled with adventure and discovery.

Green

Plan your stay in Green, a top-rated choice for families and nature lovers looking for a blend of outdoor adventure and scenic beauty. Just a short drive from Winston, Green offers easy access to attractions like the Douglas County Museum of History and Natural History, the picturesque South Umpqua River, and the serene Stewart Park. With a steady flow of visitors year-round, Green is a smart hotel booking choice for those eager to explore the great outdoors.

Dillard

Families and outdoor enthusiasts will love Dillard, known for its stunning natural scenery and recreational activities. This charming village in Winston offers access to the South Umpqua River for adventurous outings, the Douglas County Museum for a bit of local history, and Stewart Park for leisurely afternoons. With seasonal visitor peaks in March, May, and September, Dillard ensures a vibrant atmosphere. Its strategic location makes it a smart choice for your next getaway.

Myrtle Creek

Ideally situated for family and nature-loving travelers, Myrtle Creek offers a charming escape with easy access to outdoor adventures and scenic beauty. Visitors can explore the nearby national and state parks, enjoy the serene lake, or unwind at local attractions like Millsite Park and Myrtle Creek Memorial Park. Located about 9 miles by car from Winston, Myrtle Creek is a smart choice for those looking for an affordable getaway that combines relaxation with recreation.

Tenmile

Looking for the perfect spot? Tenmile is an ideal base for travelers seeking family-friendly adventures and nature experiences in Winston, Oregon. Here, you can enjoy activities like visiting the South Umpqua River, exploring Stewart Park, or discovering local history at the Douglas County Museum. With its picturesque scenery and outdoor appeal, Tenmile attracts visitors year-round, especially from June to August. It’s just about an 11-mile drive from Winston, making it a smart choice for your getaway.

Discover the most popular places to visit in Winston

Winston Hotel Deals

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.

Frequently Asked Questions

How much does a Winston vacation package cost?

Offering excellent value package deals from $513 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?

  1. Pick your travel dates: The things you want to do in Winston and your preferred season will help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.