Discover Your Perfect Winston Vacation Homes

Winston Pet Friendly Vacation Rentals

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9.0 (281 Reviews)
Hotel
Hampton Inn & Suites Roseburg
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Pet-Friendly Vacation Rentals in Winston on PetFriendly.io

Why Choose Rent By Owner for your Winston Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Winston

When should you plan your Vacation Rentals stay?

To make the most of your stay, consider visiting during the region’s peak seasons when the weather is most inviting and local activities are in full swing, ensuring an enjoyable and memorable experience here in Winston, Oregon.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you'll enjoy pleasant weather ideal for exploring the outdoors and local activities in this area.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

Autumn offers a vibrant landscape with colorful foliage, making it a picturesque time to visit and experience the region's natural beauty.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

The winter months bring cooler temperatures and quieter surroundings, providing a peaceful retreat for visitors seeking tranquility.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F
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Spring (March to May)

Springtime sees a gradual warming and blooming season, offering fewer crowds and excellent opportunities to enjoy nature at a relaxed pace.

Average Temperature Daytime: 55°F to 65°F - Nighttime: 40°F to 50°F

Weekly Weather Forecast for Winston

How to Book Your Winston Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Winston

More Top-Rated Vacation Rentals in Winston Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy spacious outdoor patios or decks perfect for relaxing and dining al fresco.
  • Take advantage of private gardens or lush yard spaces ideal for outdoor activities.
  • Make use of outdoor grilling areas to prepare meals while enjoying the fresh air.
  • Benefit from access to scenic walking trails or nearby nature paths in the region.
  • Relax by a private or community swimming pool, especially popular during warmer months.
  • Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
  • Explore well-maintained lawns and open spaces suitable for outdoor games and family fun.

Top Attractions Around Winston

What attractions are nearby?

While staying here, you'll find a variety of outdoor activities and local attractions nearby to explore, offering a perfect way to enjoy the natural beauty and regional charm of Winston, Oregon.

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Family Activities

  • Winston Community Park: Enjoy a day outdoors with your family at this scenic park, offering playgrounds, picnic areas, and walking trails perfect for all ages.
  • Oregon Caves National Monument: Discover fascinating limestone caverns just a short trip from here, where guided tours provide an educational adventure for the whole family.
  • Tenmile Lake: Spend a relaxing afternoon fishing, boating, or picnicking by the shores of this tranquil lake nestled in the region's natural beauty.
  • Treetop Adventure Park: Experience an exciting ropes course that challenges and entertains children and parents alike within the scenic surroundings of the area.
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Adult Activities

  • Wine Tasting Tours: Explore local wineries and savor exquisite wines as you immerse yourself in the region's renowned winemaking heritage.
  • Hiking and Nature Walks: Enjoy scenic trails through lush landscapes, offering a peaceful retreat and breathtaking views of the surrounding countryside.
  • Visit to Local Art Galleries: Discover vibrant art scenes and unique crafts created by talented regional artists, perfect for cultural enthusiasts.
  • Golfing Experiences: Tee off at nearby golf courses that promise both relaxation and a challenge amidst the area's picturesque setting.

Other Places to Stay in Winston, OR

Dillard
Dillard Vacation Rentals
Abacela Winery
Abacela Winery Vacation Rentals
Wildlife Safari
Wildlife Safari Vacation Rentals
More Places to Stay Near Winston

Winston Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take the time to discover regional eateries and farm-to-table restaurants to enjoy authentic flavors unique to this destination.
  • Connect with Nature: Make the most of your stay by visiting nearby parks and outdoor spaces that showcase the natural beauty of the area.
  • Plan Cultural Experiences: Enrich your visit by engaging in local events, art galleries, or community gatherings that reflect the region’s vibrant culture.
  • Optimize Your Accommodation Choice: Select from vacation rentals that offer comfort and convenience, ensuring a seamless and memorable experience during your time here.

Transportation Options

  • Winston Transit: The local transit system offers convenient bus routes that connect you to nearby towns and points of interest in the region.
  • Private Car Services: Reliable taxi and ride-sharing options provide flexible transportation within Winston and to surrounding areas, ideal for exploring at your own pace.
  • Rental Cars: Numerous car rental agencies operate nearby, giving you the freedom to explore this scenic destination on your schedule.
  • Biking and Walking: The area features pedestrian-friendly pathways and bike trails, perfect for experiencing Winston’s charming atmosphere up close.

Local Customs Options

  • Western Heritage Celebrations: During special events, you might observe local traditions that honor the area's pioneer history and community spirit.
  • Farmers' Market Etiquette: Visiting the weekly farmers' markets, you'll notice a friendly exchange of local produce and handcrafted goods, reflecting the area's agricultural roots.
  • Community Coffee Culture: Sharing a warm cup at neighborhood cafes, locals embrace a laid-back coffee tradition that emphasizes connection and hospitality.
  • Environmental Respect: Here, there's a strong emphasis on sustainable practices and preserving the natural beauty, visible in daily life and outdoor activities.

Frequently Asked Questions About Winston?

1. What are the top vacation rentals in Winston?

There are a lot of options in Winston. If you plan on staying in the Winston area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winston:

2. How many vacation rentals have private pools in Winston?

There are 3 vacation rentals with private pools near Winston. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Winston are best for families?

If you are looking for a family-friendly vacation home in Winston, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winston:

4. How many Rentbyowner vacation rentals are available in Winston?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 123 in the Winston area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winston. 

5. What is the cancellation policy for vacation rentals in Winston, Oregon?

The cancellation policy varies depending on the property owner and listing. To ensure you understand the terms, please review the specific cancellation details included in the listing or contact the host directly before completing your booking.

6. How do I confirm availability and secure my reservation in Winston, Oregon?

Availability can be checked through the property's listing page, where you can select your desired dates. Once you've found a suitable rental, proceed with the booking process to reserve your stay securely.

7. Are there any additional fees associated with booking a vacation rental here?

Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing details. Be sure to review the total cost during the booking process to avoid surprises.

8. What amenities are usually included in a vacation rental in Winston, Oregon?

Amenities vary between properties but commonly include essentials like Wi-Fi, parking, kitchen facilities, and linens. Detailed lists of available amenities are provided on each listing page.

9. Who should I contact if I have questions or encounter issues during my stay in Winston?

For any questions or concerns, you should reach out directly to the property owner or property manager listed on the booking page. Their contact information is provided to assist you promptly.