Winston-Salem holiday lettings

We found 591 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Winston-Salem by choosing from 223 houses, 97 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:22 May - 29 May

Image gallery for Updated 1BR cottage on private acre+ lot

Living area
10 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)

Updated 1BR cottage on private acre+ lot

Winston-Salem

8% off
Price is £676
for 7 nights, 1 home
£97 per night
includes taxes & fees
Updated 1BR cottage on private acre+ lot

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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)
  • 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)
  • 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)
  • Lake Thom-A-Lex Park (14.7 mi / 23.7 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.
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 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.
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, 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 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 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.
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 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.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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