Photo by Michelle Finseth

Winston vacation rentals

We found 42 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Winston that are perfect for your trip. Whether you're staying in a vacation rental with family, friends, or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, including WiFi and parking. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.
  • Peace of mind
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  • More quality time
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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Find out more about Winston

Find out more about Winston

Why visit Winston

  1. Outdoor Adventures: Enjoy stunning scenery with hiking, fishing, and river explorations in and around Winston.
  2. Family-friendly Activities: Engage in various activities suitable for families, enhancing your vacation experience.
  3. Historic Museums: Discover local history at engaging museums that showcase Winston's rich heritage.
  4. Charming Accommodations: Choose from cozy cabins and charming cottages to make your stay comfortable and memorable.
  5. Nearby Urban Excursions: Explore the vibrant city of Vancouver for a contrasting urban experience.

Popular types of accommodation in Winston

Planning a getaway to Winston? The excitement begins with selecting the perfect accommodation! From charming cottages and cozy cabins to spacious houses, Winston offers a variety of options to suit your needs. Explore enticing Winston vacation rentals, including apartments and house rentals, to make your stay truly memorable. Discover the ideal spot for your adventure today!

  • Houses: The top choice for visitors to Winston, these homes offer spacious accommodations ideal for families or groups seeking a home-away-from-home experience.
  • Cottages: A delightful option for a quaint and cozy retreat, perfect for those who appreciate a charming atmosphere.
  • Cabins: These rustic lodgings provide a peaceful escape for nature enthusiasts, surrounded by stunning landscapes.
  • Condos: A modern and convenient choice, condos offer great amenities and are perfect for shorter stays.
  • Apartments: Ideal for solo travellers or couples, these rentals provide a comfortable and budget-friendly option.**

Top attractions in Winston

Winston, Oregon, is a delightful destination for outdoor enthusiasts and families alike, offering stunning scenery and a mix of urban experiences. Visitors can explore picturesque rivers, engaging history museums, and well-maintained urban parks. Whether you're travelling solo or with loved ones, Winston provides a range of attractions that cater to all interests, ensuring a memorable vacation filled with adventure and relaxation.

  1. South Umpqua River: A stunning natural gem, this river offers picturesque scenery and a serene outdoor atmosphere, perfect for fishing, kayaking, or simply enjoying nature's beauty.
  2. Douglas County Museum of History and Natural History: This museum showcases the rich cultural heritage and natural history of the region, featuring engaging exhibits that bring the area's past to life.
  3. Stewart Park: A family-friendly urban park with ample green space, playgrounds, and picnic areas, ideal for outdoor activities and enjoying the vibrant city vibes.

Things to do recommended for couples

For a romantic getaway in Winston, explore the charming Abacela Winery for its enchanting atmosphere. Just a short drive away, Spangler Vineyards and Pyrenees Vineyard & Cellars offer delightful tastings amidst picturesque settings, perfect for couples seeking a memorable experience together.

Things to do recommended for families

Experience the tranquility of Stanton Park, a recreation area 22.5km from Winston, perfect for family relaxation. Alternatively, visit Herbert's Pond Park, located 24.1km away, offering a serene environment for outdoor enjoyment and wellness activities.

Things to do recommended for groups

Groups visiting Winston, Oregon can enjoy a fun evening at the nearby Seven Feathers Casino, experience the thrill of golf at Cougar Canyon or Umpqua Golf Resort, both offering gorgeous outdoor settings perfect for sports enthusiasts.

What do I need to keep in mind when booking a vacation in Winston

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Winston with a group: Think about how many bedrooms you’ll require, as well as any amenities like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Winston with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety while also looking for age-appropriate amenities, like a private swimming pool. Additionally, consider how close you are to family-friendly attractions to enhance your experience.
  • Taking your pets with you to Winston: For many families, a vacation isn’t truly fulfilling without their furry companion. If this resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Winston: If you're searching for vacation rentals that offer savings for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don’t forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in Winston

Winston, Oregon, offers a delightful blend of outdoor adventures and family-friendly activities. Visitors can explore the charming local buildings and experience the welcoming atmosphere of friendly folks. Nearby, the vibrant city of Vancouver presents an exciting contrast with its bustling downtown scene. Whether you're looking for budget-friendly options or a serene escape, Winston and its surroundings promise a memorable vacation tailored to all travellers.

  • Roseburg: Located a mere 11.3km from Winston, Roseburg is a charming city that beckons outdoor enthusiasts and adventure seekers alike. Known for its stunning scenery, visitors can enjoy a variety of recreational activities, from exploring the nearby national and state parks to relaxing at local lakes. The city also features a vibrant casino and resort, offering entertainment options for those looking to unwind after a day of exploration. With its picturesque landscapes and outdoor adventures, Roseburg is a perfect escape for nature lovers.
  • Green: Just 4.8km from Winston, the quaint village of Green is a hidden gem for those who appreciate the great outdoors. With abundant trail access and hiking opportunities, it's an ideal spot for a day of exploration amidst nature. The surrounding national and state parks provide a breathtaking backdrop for outdoor activities, while the nearby lakes offer serene spots for fishing or picnicking. Green is perfect for those seeking a peaceful retreat in a scenic setting.
  • Dillard: Nestled in the vicinity of Winston, Dillard is a charming village that caters to families and nature lovers. The area is known for its recreational spaces, making it a great spot for family outings and outdoor fun. Visitors can explore the nearby rivers and enjoy the beauty of water features that enhance the village's natural charm. With its welcoming atmosphere and scenic surroundings, Dillard is a wonderful place for a relaxing getaway.

Best time to go to Winston

If you're planning a trip to Winston, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January40.3°F (4.6°C)Light RainMostly CloudyAverageSlightly Low
February40.3°F (4.6°C)Light RainMostly CloudyAverageAverage
March42.6°F (5.9°C)Light RainMostly CloudyModerately HighAverage
April46.6°F (8.1°C)Light RainMostly CloudyAverageAverage
May52.5°F (11.4°C)Light RainMostly SunnyAverageAverage
June58.3°F (14.6°C)No Rain (Dry)Mostly SunnyModerately HighAverage
July64.4°F (18.0°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
August64.9°F (18.3°C)No Rain (Dry)SunnyAverageSlightly High
September60.1°F (15.6°C)No Rain (Dry)Mostly SunnyAverageSlightly High
October52.0°F (11.1°C)Light RainMostly SunnyModerately LowAverage
November43.7°F (6.5°C)Light RainMostly CloudyModerately LowSlightly Low
December38.7°F (3.7°C)Light RainMostly CloudyModerately LowSlightly Low

Booking with Vrbo is simple

Are you aiming to save on your upcoming journey? It’s wise to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We’re here to help you find the best options for your needs.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform for planning your travels, allowing you to create new trips, continue from where you last stopped, or manage your existing plans. You'll be able to easily access the properties you’ve saved or booked, organized under categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Travel to trendy Winston

The wildlife and other outdoor surroundings create an inviting atmosphere in Winston. This trendy city allures visitors with its safari tours and restaurants. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Winston

Are you hoping to find things to do during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Winston has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Wildlife Safari (1.4 mi / 2.3 km)
  • Melrose Vineyards (9.6 mi / 15.5 km)
  • Reustle Prayer Rock Vineyards (15.6 mi / 25.1 km)
  • Abacela Winery (1.9 mi / 3 km)
  • Spangler Vineyards (2.6 mi / 4.2 km)
  • Girardet Wine Cellars (8.4 mi / 13.5 km)

Exploring the natural features in Winston

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Winston is a great place to get out in nature. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • South Umpqua River (0.7 mi / 1.1 km)
  • Stewart Park (7 mi / 11.2 km)
  • Winchester Dam (11.6 mi / 18.6 km)
  • Millsite Park (9.1 mi / 14.7 km)
  • Stinebaugh Park (9.1 mi / 14.7 km)
  • Myrtle Creek Memorial Park (9.3 mi / 14.9 km)

Frequently asked questions

What is the most popular type of vacation rental accommodation in Winston?
The most desirable types of vacation rentals in Winston are houses. Searching for something different? Vrbo has a variety of options to match the unique needs of our guests, so you’ll see properties in lots of sizes and shapes. The ideal fit is ready and waiting for you — book yours today.
How much does it cost to rent a vacation rental in Winston?
The average price for a vacation home in Winston is based on several factors, such as length of stay, property type and season. Whether you’re thinking about a villa with space for extended family or a quaint cabin just enough for two, just add your dates of travel to see stays that offer great value.
How much does it cost to rent a beach house in Winston?
When you travel and the style and size of the property will influence how much you’ll pay for your beachside stay. Put in your Winston travel dates to view your options on Vrbo. Did someone just say “private pool”? Use our filters to pick the features and amenities you want.
Are there pet-friendly vacation rentals in Winston?
Yes. Choose from two vacation homes that welcome pets in Winston on Vrbo. Our furry friends need to get away from it all too, so simply use our search function for pet-friendly vacation rentals to book a perfect pad where your puppy can be near his favorite humans.
What are popular rental amenities in Winston?
When it comes to rental amenities that guests prefer in Winston, a garden, a barbecue grill and a fireplace rank the highest. With Vrbo vacation rentals, you’ll find options to suit your taste and style, whether you’re going on a trip with your partner, your family or even pets.
Are there vacation rentals in Winston that welcome kids?
Winston has two family-friendly vacation rentals to choose from. And tracking down a stay that welcomes kids is a breeze with our “Properties good for families” filter. As well as having the whole place to yourselves, you can also look forward to perks and amenities such as extra bedrooms, kitchens and yards.
What are the top attractions for families in Winston?
Keep your kids occupied at these awesome family-friendly attractions in Winston:

  • Wildlife Safari
  • Douglas County Museum of History and Natural History
  • South Umpqua River

How can I find vacation rentals with air conditioning in Winston?
Winston has two vacation rentals where you’ll be able to chill out in air-conditioned comfort. To book a property on Vrbo that has this amenity, enter your dates of travel and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Winston?
The minimum age requirements can vary across properties on Vrbo, so look at the rules of the vacation rental in Winston you’re interested in. But usually, it’s 16, 18 or 21.
How long can I rent a vacation rental in Winston for?
The amount of time you can book a Winston vacation rental for differs depending on the property. Simply put in your dates of travel to find options offering extended stays. They include everything you need to make your extended break more enjoyable like kitchens and yards. Some vacation homes might also offer weekly or monthly discounts, so you can stick around for longer for less.

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