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  3. Winston
  4. Rentals by Owner

Discover Your Perfect Winston Rentals by Owner

Winston Rentals by Owner

More Top-Rated Rentals by Owner in Winston Area

Why Choose Rent By Owner for your Winston vacation rental?

What makes our Rentals by Owner 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 Rentals by Owner stay?

Understanding the best time to vacation here can help you enjoy your stay in Winston, North Carolina, USA, to the fullest, ensuring you select the perfect season for your preferred activities and experiences through Rent By Owner's reliable rental options.

Peak Season Highlights

spring
Spring (March to May)

During the spring months, you can enjoy the region's pleasant weather and lush landscapes, making it an ideal time for exploring and outdoor activities. Booking a rental here during this season ensures you'll experience the area's vibrant natural beauty at its best.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
autumn
Fall (September to November)

Autumn showcases stunning foliage and mild temperatures, drawing visitors seeking scenic views and comfortable weather. Securing your rental during this time allows for a cozy stay amidst the region’s colorful fall scenery.

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Off-Season Highlights

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Winter (December to February)

Winter is quieter here, with cooler temperatures and less tourist traffic, offering a peaceful retreat. This is an excellent period to find more affordable rental options and enjoy a relaxing visit without the crowds.

Average Temperature Daytime: 45-55°F - Nighttime: 25-35°F
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Summer (June to August)

Although summer brings warmer weather, this time of year can be busier due to vacations, but it also offers longer days and opportunities for seasonal activities. Off-peak bookings may provide better rates and availability for your stay in the region.

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Weekly Weather Forecast for Winston

How to Book Your Winston vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Rentals by Owner in Winston Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 outdoor seating areas such as patios or decks to relax and unwind in the fresh air.
  • Take advantage of landscaped gardens or expansive yards perfect for outdoor activities.
  • Look for private balconies that offer scenic views of the surrounding region.
  • Make use of outdoor grilling stations or picnic areas for memorable meals al fresco.
  • Access swimming pools or hot tubs available on the property for added relaxation.
  • Explore well-maintained walking trails or nature paths nearby for outdoor exploration.
  • Utilize spacious parking spaces or garages designed to accommodate your outdoor gear and vehicles.

Top Attractions Around Winston

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities and local attractions that allow you to experience the region’s unique character and natural beauty.

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Family Activities

  • North Carolina Museum of Transportation: Discover fascinating vintage trains and interactive exhibits that make exploring the region's transportation history engaging for the whole family.
  • Hanging Rock State Park: Enjoy outdoor adventures with hiking, picnicking, and scenic views in this natural setting just outside the city, ideal for family outings.
  • Kerr Vance Pool & Waterpark: Cool off and have fun swimming or enjoying water slides at the local aquatic park, perfect for a warm day with kids.
  • Tanglewood Park: Experience family-friendly activities such as horseback riding, walking trails, and seasonal events in a peaceful park setting nearby.
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Adult Activities

  • Explore the North Carolina Museum of Winston-Salem: Discover captivating art and history exhibits that showcase the area's rich cultural heritage.
  • Stroll through Old Salem Museums & Gardens: Immerse yourself in the historic Moravian community with engaging tours and beautifully preserved architecture.
  • Relax at Salem Lake Park: Enjoy outdoor activities such as fishing, walking, or picnicking around this scenic reservoir located nearby.
  • Experience local flavors at downtown Winston-Salem restaurants: Savor diverse culinary offerings that highlight regional ingredients and vibrant food scenes.

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Winston Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Events and Festivals: Engage with the area's vibrant community by attending local gatherings to enhance your stay in Winston and experience authentic regional culture.
  • Choose a Strategic Location: Select a rental near key attractions or amenities to maximize your time exploring and minimize travel within this welcoming destination.
  • Investigate Nearby Outdoor Activities: Take advantage of the region's natural beauty by scheduling outdoor adventures like parks or trails accessible from your accommodation.
  • Consult Your Rental Host for Insider Tips: Reach out to your host to discover hidden gems and local favorites that will enrich your visit here in Winston and the surrounding region.

Transportation Options

  • Winston-Salem Transit Authority (WSTA): You can rely on this local bus service for convenient transportation throughout the area, making it easy to explore from your rental.
  • Rental Car Services: Major providers are available in Winston, offering flexible options to navigate the region at your own pace and schedule.
  • Taxi and Rideshare Services: Ride-hailing apps and taxi companies provide quick, dependable transportation for getting around here efficiently.
  • Bike Rentals and Cycling Routes: For a more active approach, bike rentals and dedicated cycling paths allow you to enjoy the area's scenic views at your leisure.

Local Customs Options

  • Southern Hospitality: You’ll find that friendliness and warm welcomes are a cherished part of local customs here, making your stay in this welcoming region even more enjoyable.
  • Participating in seasonal festivals and local gatherings offers you a genuine glimpse into the area's vibrant culture and traditions.
  • Respect for History: The community takes pride in preserving its history, so when exploring the area, it’s appreciated if visitors honor local landmarks and historical sites.
  • Food and Culinary Traditions: Savoring regional specialties and engaging with local eateries allows you to experience authentic flavors that reflect the area’s rich culinary heritage.

Frequently Asked Questions About Winston Rentals by Owner

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 Rentbyowner vacation rentals are available in Winston?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 580 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. 

3. What is the cancellation policy for rental by owner properties in Winston, North Carolina?

Cancellation policies vary by individual listing. To ensure you understand the specific terms, please review the cancellation details provided on the rental's listing page or contact the property owner directly before completing your booking.

4. How do I confirm the availability of a rental by owner in Winston, North Carolina?

Availability is typically displayed on the listing page. For real-time confirmation, it's best to reach out to the property owner through the booking platform or check the calendar provided on the listing.

5. Are there any additional fees I should be aware of when booking a rental by owner in this area?

Additional fees such as cleaning charges, service fees, or security deposits are often itemized on the listing. Review the detailed fee section or contact the owner if you have questions about extra costs before booking.

6. What amenities are generally included in rentals by owner here?

Amenities can differ between properties, so it’s important to read each listing carefully. Common features include Wi-Fi, parking, and kitchen facilities, but confirm specific amenities with the owner directly to meet your needs.

7. How do I communicate with the property owner for special requests or inquiries in Winston, North Carolina?

Most listings offer direct messaging options or contact information. Reach out early to discuss any special requests or questions to ensure a smooth stay during your visit to the region.

More Rentals You May Like Near Winston

More Top-Rated Rentals by Owner in Winston Area