Winston-Salem holiday lettings

We found 529 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Winston-Salem by choosing from 192 houses, 95 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:5 Dec - 12 Dec

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Wonderful
(6 reviews)

Nice CozyHome, Winston-Salem

Winston-Salem, NC

8% off
Price is £927
for 7 nights, 1 home
£132 per night
includes taxes & fees
Nice CozyHome, Winston-Salem

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Find out more about Winston-Salem

Find out more about Winston-Salem

Why visit Winston-Salem

  • Cultural richness: Explore a variety of art museums and historic villages that showcase Winston-Salem's vibrant heritage.
  • Charming neighbourhoods: Discover delightful areas like Karmel Hill, perfect for leisurely strolls and local experiences.
  • Family-friendly activities: Enjoy numerous attractions that cater to all ages, ensuring fun for the entire family.
  • Diverse accommodation options: Choose from quaint private holiday homes, cosy apartments, and charming cabins for a memorable stay.
  • Outdoor adventures: Take advantage of the beautiful surroundings with opportunities for hiking and exploration.

Popular types of accommodation in Winston-Salem

Planning a getaway to Winston-Salem? The next exciting step is selecting your accommodation. Discover a variety of options, including charming houses, cosy apartments, and delightful cabins. With numerous rental listings and properties available, you can easily find the perfect home for rent to suit your needs. Explore the vibrant offerings of Winston-Salem rentals and make your stay truly memorable.

  • Houses: The most sought-after option in Winston-Salem, offering ample space and privacy for families or groups.
  • Apartments: A popular choice for those seeking a convenient and modern base to explore the city.
  • Cabins: Ideal for nature enthusiasts, these rentals provide a serene escape in a rustic setting.
  • Cottages: Charming and quaint, perfect for a romantic getaway or a tranquil retreat.
  • Condos: A stylish option that combines comfort with access to amenities.**

Top attractions in Winston-Salem

Winston-Salem is an ideal destination for city-themed, family, and outdoor holidays. Visitors can explore a range of attractions, including modern colleges, historic villages, and art museums, offering enriching cultural experiences. Whether you're seeking family fun or an immersive city experience, Winston-Salem has something to delight every traveller.

  • Wake Forest University: A prestigious modern university, Wake Forest boasts a beautiful campus with a blend of traditional and contemporary architecture. Its vibrant atmosphere is perfect for exploring art galleries, libraries, and lush green spaces.
  • Benton Convention Center: This dynamic event venue is ideal for conferences and exhibitions. Its modern facilities and business-centric vibe make it a hub for professionals and visitors alike, hosting a variety of events throughout the year.
  • Old Salem: A charming historic village, Old Salem offers a glimpse into the Moravian community's past. Wander through restored buildings, enjoy traditional crafts, and savour authentic cuisine in a picturesque setting that reflects rich cultural heritage.

Things to do recommended for couples

For a delightful couple's getaway in Winston-Salem, explore the enchanting Weathervane Winery, only 8.1km away, or visit the charming Junius Lindsay Vineyard, situated 7.5km from the city. Don't miss Medaloni Cellars and Vineyards, a romantic escape just 8.7km away, perfect for wine lovers.

Things to do recommended for families

Families visiting Winston-Salem can enjoy the energetic atmosphere at Lawrence Joel Veterans Memorial Coliseum and Truist Stadium, perfect for sports enthusiasts. For a day of adventure, head to Airbound Trampoline Park, where kids can bounce around and have great fun together.

Things to do recommended for groups

Groups visiting Winston-Salem can indulge in shopping at Hanes Mall, enjoy thrilling races at Bowman Gray Stadium, and catch a film at Grand 18-Winston-Salem, making for a delightful blend of shopping, sports, and entertainment suitable for all ages.

What do I need to keep in mind when booking a vacation in 'Winston-Salem

If you're travelling with a group, as a family, with pets, or seeking extended stays, it's important to use the appropriate filters to prioritise your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winston-Salem with a group: Think about how many bedrooms you'll require, as well as features like a fully-equipped kitchen or outdoor area for group gatherings. Luckily, you can easily apply filters for these options and many more on Vrbo.
  • Traveling to Winston-Salem with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Winston-Salem: For many, a family holiday wouldn’t be the same without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winston-Salem: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. It may also be beneficial to include amenities such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in and around Winston-Salem

Winston-Salem, North Carolina, offers a delightful blend of family-friendly activities and vibrant city life. Visitors can explore charming neighbourhoods like Karmel Hill, indulge in local excursions, and enjoy the warm atmosphere created by friendly locals. Whether you're seeking outdoor adventures or a cultural experience, Winston-Salem and its surrounding areas promise a memorable holiday filled with diverse vibes and exciting discoveries.

  • Winston-Salem: Winston-Salem is a vibrant city known for its rich history and modern charm. Nestled in the heart of North Carolina, it offers a delightful blend of family-friendly activities and business opportunities. Visitors can explore the local shopping centres, enjoy educational institutions, and relax by the scenic lake. The city is home to notable landmarks such as a prestigious modern college university and a lively stadium, making it an excellent destination for both leisure and work.
  • Kernersville: Located approximately 6.2km from Winston-Salem, Kernersville is a picturesque city perfect for those seeking outdoor adventures and scenic beauty. This charming area is ideal for families, offering a variety of activities, including visits to local educational facilities and an arena entertainment complex. Nature enthusiasts will appreciate the lovely lakes and expansive parks, while the proximity to a modern college university and stadium adds to its appeal as a well-rounded destination.
  • Wallburg: Wallburg is a quaint village that provides a romantic and scenic experience for visitors. Situated near Winston-Salem, this lovely area is perfect for couples and families alike, with plenty of outdoor activities to enjoy. Golf enthusiasts can take advantage of the local golf courses, while the nearby lake and educational facilities add a touch of charm. With its serene atmosphere and beautiful surroundings, Wallburg is a delightful retreat for those looking to unwind and connect with nature.

Best time to go to Winston-Salem

If you're planning a trip to Winston-Salem, it's a good idea to check both the weather and property rates. The warmest months are July and July. Peak season runs in April, April, July, July, September and September, while off-peak times, like January, November, November to December and December to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January38.5°F (3.6°C)Light RainMostly SunnySlightly LowSlightly Low
January38.5°F (3.6°C)Light RainMostly SunnySlightly LowSlightly Low
February42.4°F (5.8°C)Light RainMostly SunnyAverageSlightly Low
February42.4°F (5.8°C)Light RainMostly SunnyAverageSlightly Low
March49.1°F (9.5°C)Light RainMostly SunnyAverageSlightly Low
March49.1°F (9.5°C)Light RainMostly SunnyAverageSlightly Low
April58.3°F (14.6°C)Light RainMostly SunnySlightly HighSlightly High
April58.3°F (14.6°C)Light RainMostly SunnySlightly HighSlightly High
May67.1°F (19.5°C)Light RainMostly SunnyAverageSlightly High
May67.1°F (19.5°C)Light RainMostly SunnyAverageSlightly High
June75.0°F (23.9°C)Light RainMostly SunnyAverageAverage
June75.0°F (23.9°C)Light RainMostly SunnyAverageAverage
July78.8°F (26.0°C)Light RainMostly SunnySlightly HighAverage
July78.8°F (26.0°C)Light RainMostly SunnySlightly HighAverage
August76.8°F (24.9°C)Light RainMostly SunnyAverageAverage
August76.8°F (24.9°C)Light RainMostly SunnyAverageAverage
September71.1°F (21.7°C)Light RainMostly SunnySlightly HighAverage
September71.1°F (21.7°C)Light RainMostly SunnySlightly HighAverage
October60.4°F (15.8°C)Light RainMostly SunnyAverageSlightly High
October60.4°F (15.8°C)Light RainMostly SunnyAverageSlightly High
November48.9°F (9.4°C)Light RainMostly SunnySlightly LowAverage
November48.9°F (9.4°C)Light RainMostly SunnySlightly LowAverage
December43.0°F (6.1°C)Light RainMostly SunnySlightly LowAverage
December43.0°F (6.1°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, opting for a longer stay often results in substantial savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy platform for you to plan new trips, resume from where you last stopped, or review and arrange your travel plans. You'll discover your saved or booked properties neatly organised into categories such as Potential, Upcoming, or Current Trips. To begin utilising Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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)
  • 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)
  • Kersey Valley Attractions (20.8 mi / 33.5 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)
  • 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)
  • Oak Hollow Lake (14.9 mi / 24 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 a holiday rental in Winston-Salem, the Historic Old Salem district is an excellent choice. This charming area is renowned for its beautifully preserved Moravian architecture and rich cultural heritage. Staying here allows easy access to the Old Salem Museums & Gardens, where you can immerse yourself in the history of the Moravian community, as well as enjoy the picturesque gardens and historic buildings. The district offers a good number of rental properties, suiting a variety of preferences, from quaint cottages to modern apartments.

Another appealing neighbourhood is the Downtown Winston-Salem area. This vibrant part of the city is home to a number of restaurants, bars, and shops, providing a lively atmosphere. The nearby Reynolda House Museum of American Art is a highlight, showcasing an impressive collection of American art in a stunning historic home. Additionally, the Innovation Quarter adds a unique modern touch to the downtown experience, making it a great place for those seeking a blend of culture and contemporary life. With a solid selection of properties available, you're sure to find something that suits your needs while enjoying the dynamic surroundings.
How much does it cost to rent a holiday home in Winston-Salem?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winston-Salem to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winston-Salem holiday house rentals?
You can find great discounts on house rentals in Winston-Salem on Vrbo, 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.
What is the most popular type of holiday rental accomodation in Winston-Salem?
In Winston-Salem, holiday houses are the most popular type of accommodation, with around 153 available across the city. These houses are often situated in residential neighbourhoods, providing a comfortable and homey atmosphere. Most holiday houses come with multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups looking to enjoy the city and its attractions, such as the Reynolda House and Old Salem.
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 122 options to choose from. The city features various neighbourhoods, each offering unique charm and proximity to local attractions. Areas like Reynolda Village provide spacious homes with large backyards, ideal for children to play in, while also being close to the stunning Reynolda Gardens and the historic Reynolda House Museum of American Art.

Visitors can expect amenities such as fully equipped kitchens, comfortable living rooms, and sometimes even game rooms for family entertainment. Many properties also include outdoor patios or decks, great for barbecues or simply enjoying the pleasant weather.
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 mix of suburban neighbourhoods and more bustling areas, where travellers can find properties that provide a relaxing getaway. Many of these rentals come equipped with private pools, inviting hot tubs, and spacious outdoor areas great for enjoying the pleasant North Carolina weather.
Can I find long-stay holiday rentals in Winston-Salem?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winston-Salem?
In Winston-Salem, there are numerous pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these properties offer amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups.

The historic West End neighbourhood is particularly appealing, featuring charming homes with character, along with proximity to parks like the Reynolda Gardens, where both pets and their owners can enjoy leisurely strolls among beautiful landscapes. Additionally, the area boasts pet-friendly cafes and local shops, ideal for those travelling with pets.
Are there any remote work holiday rentals in Winston-Salem?
In Winston-Salem, North Carolina, there are a variety of remote work holiday rentals available, with approximately 217 options to choose from. This vibrant city offers a blend of historic charm and modern amenities, making it an excellent choice for those working remotely. Many properties come equipped with essential remote work amenities, including Wi-Fi, dedicated desks, and comfortable office chairs, ensuring a productive environment. Some rentals may even feature additional conveniences such as computer monitors and office spaces, allowing for a seamless work experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winston-Salem holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
What are popular rental amenities in Winston-Salem?
In Winston-Salem, popular holiday rentals often feature a range of convenient amenities that enhance the stay for travellers. Most properties come equipped with kitchens, allowing guests to prepare their own meals, along with essential appliances such as microwaves, stovetops, and refrigerators. Additionally, cookware, dishware, and utensils are typically provided, making dining in a comfortable experience. This selection of amenities caters well to visitors looking for a cozy feel during their time in the city, whether they are exploring the historic Old Salem, the vibrant arts district, or enjoying the beautiful parks.
When is the best time to visit Winston-Salem for a holiday rental?
The best time to book a holiday rental in Winston-Salem is during the peak season from July to September, when travellers flock to this vibrant city. July, in particular, is a popular month, characterised by warm temperatures averaging around 30°C, superb for outdoor activities and exploring the area's rich cultural heritage.

During these summer months, visitors can experience firsthand a variety of festivals and events, such as the lively North Carolina Black Repertory Company's annual production, which showcases local talent. The comfortable evenings are ideal for strolling through the historic downtown, enjoying local cuisine, or attending live music performances.

If you're looking for a less crowded experience with fantastic value, consider a visit in December. While the temperatures drop to around 10°C, this month offers a unique charm with holiday decorations and events, making it a delightful time for those seeking a quieter exploration of Winston-Salem's art galleries and historic sites.
How early should I book a Winston-Salem holiday rental?
Book your Winston-Salem holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winston-Salem?
In Winston-Salem, visitors can enjoy a variety of attractions across its distinct neighbourhoods. The historic Old Salem district offers a glimpse into Moravian life with its preserved buildings and museums, making it a fascinating area to explore. Nearby, the Reynolda House Museum of American Art presents a beautiful collection of art set against the backdrop of stunning gardens, ideal for leisurely strolls.

Downtown Winston-Salem is vibrant with cultural offerings, including the Steven Tanger Centre for the Performing Arts, which hosts various performances and events. The area also features numerous dining options and boutiques, providing a lively atmosphere for visitors.
Can I change or cancel my Winston-Salem home rental booking on Vrbo?
To find Winston-Salem holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winston-Salem holiday rental prices shown on Vrbo?
Vrbo 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.

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