Winston-Salem holiday rentals

We found 577 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Winston-Salem by choosing from 210 houses, 85 apartments and other holiday rentals. Holiday rentals provide the best amenities for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Winston-Salem

Showing deals for:29 Jan - 5 Feb

Image gallery for Stunning Penthouse 15-B Located In Historic Market Square.

Grand Room at night!
10 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)

Stunning Penthouse 15-B Located In Historic Market Square.

High Point

8% off
Price is AU$11,648
for 7 nights, 1 home
AU$1,664 per night
includes taxes & fees
Stunning Penthouse 15-B Located In Historic Market Square.

Find spaces that suit your style

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    Enjoy full kitchens, laundry, pools, gardens and more

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The lush setting of Winston-Salem is ready to explore

The area's art galleries and museums are just some of the reasons to come on holiday to Winston-Salem. Renowned for its sporting events, shopping and forests, this city welcomes all visitors. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Winston-Salem

Are you hoping to discover attractions to visit in the area? Venture out of your cosy holiday rental and check out everything that makes Winston-Salem a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Medaloni Cellars and Vinyards (14 mi / 22.5 km)
  • Divine Llama Vineyards (15.1 mi / 24.4 km)
  • Cellar 4201 Vineyard (16 mi / 25.7 km)
  • Richard Childress Vineyards (17.9 mi / 28.9 km)
  • Farmington Dragway (18.8 mi / 30.2 km)
  • Celebration Station (19.8 mi / 31.9 km)

Exploring the natural landscape of Winston-Salem

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Winston-Salem is a great place to spend some time outside. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Reynolda Gardens (2.9 mi / 4.6 km)
  • Salem Lake (3.6 mi / 5.7 km)
  • Tanglewood Park (11.4 mi / 18.4 km)
  • Truist Sports Park (11.5 mi / 18.6 km)
  • BB&T Soccer Park (11.6 mi / 18.7 km)
  • Belews Lake Park (14.4 mi / 23.2 km)

Transport to and around Winston-Salem

Fly into Winston-Salem, NC (INT-Smith Reynolds), the closest airport, located 2.7 mi (4.4 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Greensboro, NC (GSO-Piedmont Triad Intl.), which is 17.1 mi (27.6 km) away.

Frequently asked questions

What is the best area to stay in Winston-Salem when booking a holiday rental?
When considering the best area to stay in Winston-Salem for a holiday rental, the Downtown district stands out as a vibrant choice. This area is not only the cultural heart of the city but also offers a variety of properties that cater to different preferences, from modern apartments to charming historic homes. In Downtown, you can easily access attractions such as the renowned Reynolda House Museum of American Art, which showcases beautiful gardens and a rich collection of artwork, and the lively Arts District, known for its galleries, shops, and restaurants.

Another excellent option is the historic West End neighbourhood, where you'll find an array of charming, well-preserved homes. This area is celebrated for its tree-lined streets and proximity to attractions like the Old Salem Museums & Gardens, which offers a fascinating glimpse into Moravian history and architecture. The West End features a more laid-back atmosphere, making it great for leisurely strolls and enjoying local cafés.

Both neighbourhoods provide a great experience of Winston-Salem, ensuring that visitors can appreciate the city's rich history and vibrant arts scene while enjoying comfortable accommodations.
What is the most popular type of holiday rental accomodation in Winston-Salem?
In Winston-Salem, holiday houses are the most popular type of holiday rental, with around 740 available throughout the city. These homes are typically situated in residential neighbourhoods, offering a spacious environment ideal for families or groups. Most holiday houses come equipped with multiple bedrooms, fully stocked kitchens, and outdoor spaces such as patios or gardens, allowing guests to relax and enjoy the local atmosphere.

Apartments also feature prominently, with about 280 options available, providing a more compact and urban experience. These rentals generally include essential amenities like kitchen facilities and comfortable living areas, great for those who prefer a city centre stay.

Additionally, there are 76 cottages and 60 condos, each offering unique charm and comfort, while a smaller selection of 28 cabins provides a rustic getaway experience.
Are there any family house rentals in Winston-Salem?
In Winston-Salem, North Carolina, there are plenty of family-friendly house rentals available, with around 125 options spread across various neighbourhoods. Areas such as Historic Bethabara Park and the charming West End are particularly popular among families, offering spacious homes that often come with multiple bedrooms and ample living spaces.

Many rentals in these areas feature practical amenities, such as fully equipped kitchens for preparing family meals, outdoor patios or decks for enjoying the pleasant Carolina weather, and sometimes even game rooms to keep the children entertained. Additionally, properties may include conveniences like laundry facilities and Wi-Fi, ensuring a comfortable stay for families.

This vibrant city is also home to attractions like the Old Salem Museums & Gardens, where visitors can take part in local history, and the Reynolda House Museum of American Art, great for a family day out.
Can I rent a holiday home with a pool or hot tub in Winston-Salem?
In Winston-Salem, there are several holiday homes available for rent that feature pools and hot tubs, with around 14 options to choose from. This charming city offers a variety of neighbourhoods where these properties can be found, including the historic Old Salem area, known for its beautifully preserved Moravian buildings and rich cultural heritage.

Travellers can expect many amenities in these rentals, including private pools for relaxation, hot tubs for unwinding after a day of exploring, and spacious outdoor areas ideal for gatherings. Many properties also come with fully equipped kitchens, allowing for convenient home-cooked meals.
Are there pet-friendly house rentals in Winston-Salem?
In Winston-Salem, there are numerous pet-friendly house rentals available, offering a range of amenities for travellers. Many properties feature spacious backyards, allowing pets to roam freely, as well as modern kitchens and comfortable living areas, superb for families or groups. Some rentals may also include additional conveniences such as laundry facilities and outdoor patios for relaxation.

The city's historical districts, such as Old Salem, provide a charming backdrop, with holiday homes often located within walking distance to parks and green spaces. Nearby, the beautiful Reynolda Gardens is a great spot for leisurely walks with pets, featuring well-maintained paths and picturesque landscapes. Additionally, the area boasts pet-friendly cafes and shops, creating a welcoming environment for travellers accompanied by their furry friends.
Are there any remote work holiday rentals in Winston-Salem?
In Winston-Salem, there are numerous remote work holiday rentals available, with approximately 1,044 options to choose from. The city offers a variety of properties that cater to remote workers, featuring amenities such as dedicated work desks and complimentary Wi-Fi, ensuring a productive environment. Many rentals also provide comfortable living spaces that allow for relaxation after a day of work.

The downtown area is particularly appealing, with its vibrant arts scene and historical landmarks, making it a great base for exploring local culture during your downtime. Additionally, properties in residential neighbourhoods often offer tranquil settings with access to parks and walking trails, great for unwinding. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Winston-Salem?
In Winston-Salem, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals comfortably. Many properties also feature onsite parking, making it convenient for those travelling by car. Additionally, rentals often come with coffee and tea makers, ensuring that guests can enjoy their favourite hot beverages at any time. Pet-friendly options are available, permitting travellers to bring their furry companions along, with some places also accommodating service animals.
When is the best time to visit Winston-Salem for a holiday rental?
The best time to visit Winston-Salem for a holiday rental is during the peak season from July to September, when the city comes alive with a vibrant setting. This period is superb for travellers seeking to immerse themselves in outdoor activities and cultural events, as the warm summer days invite exploration of the area's rich history and scenic landscapes.

July stands out as the most popular month, with temperatures typically reaching the low to mid-30s Celsius. It's an ideal time for those who enjoy outdoor pursuits, such as hiking in the nearby Blue Ridge Mountains or attending local festivals that showcase Winston-Salem's artistic flair. The pleasant evenings are superb for enjoying al fresco dining in the city's charming downtown area.

For those looking for a more budget-friendly option, consider visiting in December. While this month is quieter, it offers a unique charm, with holiday decorations and seasonal events that provide a warm, festive atmosphere. You can enjoy the local art scene and explore the stunning Reynolda Gardens without the crowds.
What are the top attractions in Winston-Salem?
In Winston-Salem, visitors can discover a mix of historical and cultural attractions across various neighbourhoods. The Old Salem area is particularly great, featuring beautifully preserved Moravian buildings and museums that showcase the city's rich history. Here, you can explore the charming streets, enjoy traditional Moravian food, and visit the Salem Museum.

In the downtown area, the Winston-Salem Arts District is vibrant with galleries, theatres, and performance spaces, making it a cultural hub. The nearby Reynolda House Museum of American Art, set in a stunning estate, offers a glimpse into the artistic heritage of the region, along with beautiful gardens to stroll through.

For those interested in nature, the Hanes Park area provides ample green space for outdoor activities, including walking and cycling trails. Additionally, the nearby Tanglewood Park features picturesque landscapes, horse riding facilities, and a variety of recreational options, great for a leisurely day out.
Are all fees included in the Winston-Salem holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Winston-Salem holiday homes with parking?
Stayz offers a wide selection of holiday homes in Winston-Salem with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Winston-Salem holiday homes?
You can find great discounts on holiday homes in Winston-Salem on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Winston-Salem holiday home booking on Stayz?
To find Winston-Salem holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winston-Salem?
A long-stay holiday home in Winston-Salem is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Winston-Salem holiday home?
Book your Winston-Salem holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winston-Salem?
Prices for holiday homes in Winston-Salem vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winston-Salem to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.