Discover Your Perfect Winderlea Vineyard and Winery Vacation Homes

Best Vacation Homes in Winderlea Vineyard and Winery

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10.0 (277 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
10.0 (2 Reviews)
House
  • Parking
  • Security/Safety
  • Barbecue/Outdoor Cooking
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10.0 (58 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
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9.2 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
10.0 (1 Review)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
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9.0 (5 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

Why Choose Rent By Owner for your Winderlea Vineyard and Winery 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 Winderlea Vineyard and Winery

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here ensures you experience the region’s finest weather and vibrant vineyard activities, making for an unforgettable getaway in this renowned Oregon destination.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, the area experiences warm weather ideal for enjoying outdoor wine tasting and vineyard tours at this popular destination in Oregon.

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

In the fall, you can experience the vibrant harvest season with picturesque vineyard views and a lively atmosphere in the region's renowned wine country.

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)

During winter, the cooler temperatures create a peaceful setting for cozy stays and intimate tastings within the region’s vineyards.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 40°F
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Spring (March to May)

Spring offers a quieter time for visiting, with blossoming vines and mild weather that make exploring the area more relaxed and enjoyable.

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

Weekly Weather Forecast for Winderlea Vineyard and Winery

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.

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 private outdoor seating areas perfect for relaxing amidst the scenic vineyards.
  • Take advantage of spacious patios or decks with beautiful views of the surrounding winery landscapes.
  • Benefit from access to lush, well-maintained gardens that add to your outdoor experience.
  • Make use of nearby walking trails that wind through the picturesque vineyard region.
  • Relax by a cozy outdoor fire pit, ideal for evenings under the stars.
  • If available, you can explore outdoor dining setups with picnic tables overlooking the vineyard.
  • Discover opportunities for outdoor wine tasting experiences in the scenic setting of this destination.
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Family Activities

  • Wine Tasting Tours: Enjoy the family-friendly wine tasting experiences offered at the vineyard, where you can explore local wines and learn about the winemaking process in a scenic setting.
  • Vineyard Picnics: Pack a picnic and relax amidst the lush vineyards, offering a peaceful outdoor activity that everyone in the family can enjoy together.
  • Educational Winery Tours: Take part in guided tours that provide insights into sustainable viticulture and winemaking techniques, making it a fun learning experience for children and adults alike.
  • Scenic Garden Walks: Stroll through beautifully maintained gardens around the estate, offering picturesque views and a relaxing atmosphere suitable for family exploration in this lush region.
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Adult Activities

  • Wine Tasting Tours: Indulge in guided wine tastings at the renowned vineyard, experiencing the region’s acclaimed varietals firsthand.
  • Vineyard Walks: Take a leisurely stroll through the sprawling vines to learn about the winemaking process and enjoy scenic views unique to this destination.
  • Private Wine Cellar Experiences: Enjoy exclusive access to private wine cellars for a tasting session that offers a deeper appreciation of local craftsmanship.
  • Wine and Food Pairing Events: Participate in expertly curated pairing events that highlight the region’s culinary delights paired with exceptional local wines.

Winderlea Vineyard and Winery Travel Tips

How Can You Make the Most of Your Stay?

  • Plan your visit during the harvest season: Experience the region’s vibrant wine culture by scheduling your stay when the grapes are being harvested for an authentic vineyard experience.
  • Explore local wine tastings and cellar tours: Maximize your time here by booking guided tastings to deepen your appreciation for the area’s renowned wines and winemaking process.
  • Book accommodations close to the vineyard: Choosing a rental nearby will give you easy access to the scenic beauty and tranquility of this wine-rich destination, allowing for more relaxed exploration.
  • Take advantage of personalized experiences: Look for opportunities to arrange private vineyard visits or wine pairing dinners to enjoy the region’s culinary and viticultural excellence fully.

Transportation Options

  • Car Rental Services: Renting a car provides flexibility to explore the scenic vineyards and charming towns in this region at your own pace.
  • Public Transportation: Local bus options offer an affordable way to navigate the area surrounding the vineyard and discover nearby attractions.
  • Private Shuttle Services: Convenient shuttle options are available for direct transportation from major airports or hotels directly to this destination.
  • Taxis and Rideshare: Taxis and rideshare apps like Uber and Lyft offer quick, reliable transportation throughout this part of Oregon.

Local Customs Options

  • Welcoming Tastings: Visitors often find that local customs here include generous and educational wine tastings, emphasizing the region’s deep-rooted winemaking traditions.
  • Respect for the Land: It is customary to show appreciation for sustainable practices, reflecting the area's commitment to preserving its scenic vineyards and natural environment.
  • Celebration of Seasons: The community celebrates harvest festivals and seasonal events, marking important times in the vineyard’s annual cycle with lively gatherings.
  • Personalized Service: Attuned to the area's hospitality traditions, staff members typically provide personalized attention, making each guest feel uniquely welcomed at these esteemed wineries.

Frequently Asked Questions About Winderlea Vineyard and Winery?

2. How many Rentbyowner vacation rentals are available in Winderlea Vineyard and Winery?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 132 in the Winderlea Vineyard and Winery 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 Winderlea Vineyard and Winery. 

3. What is the cancellation policy for booking a vacation rental in this wine country region?

Cancellation policies vary by property; please review the specific listing details or contact the property owner directly to understand the terms and any applicable fees.

4. How can I confirm the availability of a vacation rental during my travel dates?

Availability can be checked through the listing on this site; if you have questions or need assistance, reaching out to the host will ensure you get accurate information.

5. Are there any additional fees or deposits required when booking a vacation rental?

Most properties specify additional fees or deposits in their listings. It's best to read the listing carefully or contact the owner for detailed fee information.

6. What amenities are typically included with vacation rentals in this area?

Amenities vary but often include essentials like Wi-Fi, kitchen facilities, and parking. Check each listing for a complete list of what your chosen rental offers.

7. Is it possible to request special accommodations or upgrades when booking a stay?

Yes, many hosts are willing to accommodate special requests. Contact the property owner ahead of time to discuss any specific needs or upgrades.

Best Vacation Homes in Winderlea Vineyard and Winery

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8.7 (15 Reviews)
House
  • Wheelchair Accessible
  • Balcony/Terrace
  • Accessibility