Discover Your Perfect Winston Vacation Homes

Winston Luxury Rentals

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Winston Pet Friendly Vacation Rentals

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Winston Large Vacation Homes

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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?

Knowing the best time to visit here can help you make the most of your stay, whether you're seeking the vibrant energy of peak season or a peaceful escape during quieter months in Winston, North Carolina.

Peak Season Highlights

spring
Spring (March to May)

During the spring months, the area experiences mild temperatures ideal for outdoor activities and exploring local scenery. This season attracts visitors looking to enjoy pleasant weather and vibrant natural landscapes.

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

In the fall, the region features colorful foliage and comfortable temperatures, making it a popular time for outdoor adventures and scenic drives. Visitors often seek this season for its picturesque views and crisp air.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Summer (June to August)

The summer months bring warmer weather suited for indoor retreats and quiet getaways as the area experiences less tourist traffic. It’s a great time to find more affordable vacation rentals and enjoy the peaceful surroundings.

Average Temperature Daytime: 80°F to 90°F - Nighttime: 60°F to 70°F
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Winter (December to February)

Winter offers a tranquil atmosphere with cooler temperatures, appealing to travelers seeking a cozy escape. During this time, you can often find excellent deals on vacation rentals in the area while enjoying the quiet winter landscape.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°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 a relaxing outdoor patio or deck area to unwind after a day of exploring.
  • Take advantage of private gardens or landscaped yards for outdoor activities.
  • Make the most of available grills for outdoor cooking and barbecues.
  • Spend time around a community or private outdoor swimming pool during warmer months.
  • Benefit from spacious lawns ideal for outdoor games and family gatherings.
  • Relax by an outdoor fire pit, perfect for evening conversations and marshmallow roasting.
  • Utilize scenic balconies or porches that offer picturesque views of the surrounding area.

Top Attractions Around Winston

What attractions are nearby?

In this destination, you can explore a variety of outdoor activities, cultural experiences, and local events that showcase the charm and hospitality of the region around Winston, making your stay both enjoyable and memorable.

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Family Activities

  • North Winston Park: Spend quality time outdoors with your family at this spacious park, featuring playgrounds, picnic areas, and scenic walking trails that highlight the area's natural beauty.
  • Science Center and Planetarium: Engage your children’s curiosity by exploring interactive exhibits and catching a captivating show in the state-of-the-art planetarium here in the region.
  • Winston Lake Park: Enjoy fishing, paddle boating, or simply relaxing along the shoreline of Winston Lake Park, a favorite destination for families seeking outdoor recreation in this part of North Carolina.
  • Local Historical Museum: Discover the history of the area through engaging exhibits and family-friendly activities that provide insights into the region’s rich heritage.
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Adult Activities

  • Winston-Salem Symphony: Immerse yourself in the area’s vibrant cultural scene by attending a performance at the renowned Winston-Salem Symphony, showcasing the region's rich musical heritage.
  • Old Salem Museums & Gardens: Explore the historic district's beautifully preserved Moravian architecture and engaging exhibits that offer a glimpse into the area's colonial past.
  • Körner's Folly: Visit this unique Victorian-style mansion, celebrated for its intricate design and fascinating history, providing a captivating experience right here in town.
  • Reynolda House Museum of American Art: Discover impressive American art collections set within a stunning estate, perfect for those wanting to enjoy the area's artistic and historical offerings.

Other Places to Stay in Winston, NC

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Brenner Children's
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Wake Forest University Baptist Medical Center
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Novant Health Medical Park Hospital
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Theatre Alliance
Theatre Alliance Vacation Rentals
Truist Stadium
Truist Stadium Vacation Rentals
Novant Health Forsyth Medical Center
Novant Health Forsyth Medical Center Vacation Rentals
Children's Theatre of Winston-Salem
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Home Moravian Church
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Old Salem
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Williamsburg Square
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Winston Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the region's diverse culinary scene by trying local eateries near your vacation rental to enjoy authentic flavors unique to here.
  • Plan Outdoor Activities: Make the most of the area's scenic parks and outdoor spaces for activities like hiking or picnicking, offering a perfect way to relax and connect with nature.
  • Discover Nearby Attractions: Research popular local attractions and landmarks to enrich your stay and gain a deeper appreciation of this destination’s history and culture.
  • Utilize Seasonal Events: Check out seasonal festivals or events happening during your visit to immerse yourself in the community and experience the local spirit firsthand.

Transportation Options

  • Winston-Salem Transit Authority (WSTA): This regional bus service offers reliable transportation around the area, making it easy to explore local attractions and neighborhoods.
  • Rental Cars: Several local car rental agencies provide flexible options for getting around here at your own pace, whether visiting nearby sites or traveling further afield.
  • Taxis and Rideshare Services: Taxis and popular rideshare options like Uber and Lyft are readily available, offering convenient point-to-point transportation within the city and beyond.
  • Amtrak Passenger Rail: The nearby train station provides a comfortable and scenic way to travel to and from Winston, North Carolina, connecting you with larger urban centers efficiently.

Local Customs Options

  • Southern Hospitality: You’ll notice a warm welcome and friendly attitude that exemplify the region's renowned southern hospitality here in Winston, North Carolina.
  • Local Craftsmanship: Supporting local artisans and craftspeople is a valued custom, giving you a chance to appreciate the region’s unique handmade goods.
  • Cultural Festivals: Participating in community festivals and events provides an authentic glimpse into the area's rich traditions and lively spirit.
  • Traditional Cuisine: Enjoying regional dishes rooted in Southern culinary heritage offers a delicious way to experience the local customs in Winston and nearby areas.

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 8 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 2026 is over 741 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, North Carolina?

Cancellation policies vary by listing. Be sure to review the specific property's cancellation terms on the listing page or contact the owner directly for detailed information.

6. How do I secure my booking for a vacation rental in Winston, North Carolina?

Bookings are confirmed through a secure process provided by the listing platform. You can reserve your preferred property after reviewing availability and contacting the owner if needed.

7. Are there any house rules or restrictions I should be aware of when staying in Winston's vacation rentals?

Yes, each property has its own set of house rules and restrictions listed on the property page. It's advisable to read these carefully before completing your reservation or reaching out to the owner for clarification.

8. What amenities can I expect in vacation rentals here?

Amenities vary by property. Check the listing details to see what is included, such as Wi-Fi, parking, kitchen facilities, or pet policies, to ensure the rental meets your needs.

9. Is it possible to find last-minute vacation rentals in Winston, North Carolina?

Yes, last-minute bookings are often available, but availability depends on the current demand. Contact the property owner or check the listing calendar for real-time availability.

Winston Top Rated Vacation Rentals

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