Winston-Salem vacation rentals

We found 570 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Winston-Salem by choosing from 204 houses, 91 apartments, and other vacation rentals. Vacation rentals provide the amenities you need and want for your stay with friends, family, or just your pet, such as parking and air conditioning. You'll be able to choose a rental to meet everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Winston-Salem

Showing deals for:Feb 27 - Mar 6

Image gallery for 🍀 Exceptional Fully Equipped Spacious Home 1 King & 2 Queen BRs

House Front at Daytime
9.0 out of 10, Wonderful, (6 reviews)
Wonderful
(6 reviews)

🍀 Exceptional Fully Equipped Spacious Home 1 King & 2 Queen BRs

High Point, NC

10% off
Price is CA $821
CA $6,999 total
includes taxes & fees
🍀 Exceptional Fully Equipped Spacious Home 1 King & 2 Queen BRs

Find spaces that suit your style

Find out more about Winston-Salem

Why visit Winston-Salem

  • Diverse Attractions: Experience a mix of modern colleges, art museums, and historic villages that cater to all interests.
  • Family-Friendly Activities: Enjoy a variety of engaging experiences perfect for families and visitors of all ages.
  • Charming Neighborhoods: Explore the picturesque streets of historic Salem and the vibrant Downtown Winston.
  • Outdoor Adventures: Take advantage of local parks and picnic shelters for fun outdoor activities.
  • Comfortable Accommodations: Choose from a range of vacation rentals, including private homes and cozy cabins.

Popular types of accommodation in Winston-Salem

If you're wondering about accommodation options in Winston-Salem, you're in the right place. Our most sought-after vacation rentals include houses, cozy apartments, and charming cabins. Whether you're searching for NC rentals, vacation rentals, or specific rental listings in Winston, we have a variety of home rentals and apartments to suit your needs. Enjoy your stay with confidence, knowing we've got the perfect spot for your getaway.

  • Houses: The top choice for visitors in Winston-Salem, these homes provide the comfort and space for families, couples, or groups seeking a memorable stay.
  • Apartments: A popular option for those looking for a convenient and modern living space, ideal for short or extended stays.
  • Cabins: For a rustic retreat, cabins offer a cozy atmosphere surrounded by nature, perfect for a relaxing getaway.
  • Cottages: Charming and quaint, cottages provide a homey feel, often located in scenic areas for a peaceful experience.
  • Condos: Well-suited for those who enjoy amenities and a vibrant community, condos are a great choice for a comfortable vacation.**

Top attractions in Winston-Salem

Winston-Salem is perfect for city-themed, family-friendly, and outdoor vacations. Visitors can explore a variety of attractions, including modern colleges and universities, art museums, and historic villages. These points of interest offer a diverse range of experiences, making it an ideal destination for those seeking adventure, cultural enrichment, and family activities in a vibrant setting.

  • Benton Convention Center: A hub for events and conferences, this venue offers a professional atmosphere with modern amenities, making it perfect for business gatherings and exhibitions.
  • Old Salem: Step back in time in this historic village, where you can explore preserved Moravian architecture, experience local crafts, and immerse yourself in the rich cultural heritage of the region.
  • Winston Salem State University: This vibrant institution showcases contemporary campus life, featuring diverse programs and a strong sense of community, all set within an urban environment.

Things to do recommended for couples

Winston-Salem offers delightful romantic experiences for couples. Visit Junius Lindsay Vineyard, Weathervane Winery, or Medaloni Cellars and Vineyards, each providing enchanting atmospheres just a short drive away. Savor local wines while enjoying picturesque views and creating lasting memories together.

Things to do recommended for families

In Winston-Salem, families can cheer at the Lawrence Joel Veterans Memorial Coliseum and Truist Stadium for thrilling sports events. For some active fun, visit the Airbound Trampoline Park, where adventure awaits for all ages in a lively atmosphere.

Things to do recommended for groups

Explore the vibrant atmosphere at Hanes Mall for shopping and entertainment, experience the thrill of motor racing at Bowman Gray Stadium, and enjoy a movie night at Grand 18-Winston-Salem for a memorable group outing in this charming city.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you’re planning a trip with a group, family, pets, or seeking longer accommodations, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winston-Salem with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Winston-Salem with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your location in relation to family-friendly attractions is a wise choice.
  • Taking your pets with you to Winston-Salem: For many, a family getaway wouldn’t feel complete without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. The majority of pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Winston-Salem: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. With the appropriate filters, you can conveniently discover and save on monthly rentals. Don't forget to include options like a parking spot, a well-equipped kitchen, or even a private pool in your search.

Where to stay in and around Winston-Salem

Winston-Salem, North Carolina, offers a delightful blend of family-friendly attractions and vibrant city life. Explore the charming neighborhoods, including historic Salem and lively Downtown Winston. Enjoy outdoor activities at local picnic shelters and discover unique ranch houses that showcase the area’s heritage. With its friendly atmosphere and budget-friendly excursions, Winston-Salem is perfect for a memorable vacation experience that caters to all ages.

  • Winston-Salem: Nestled in the heart of North Carolina, Winston-Salem is a vibrant city known for its rich history and diverse attractions. This urban hub offers a blend of family-friendly activities, business opportunities, and city-themed experiences. Visitors can explore local landmarks like modern colleges, serene lakes, and sports stadiums. With a variety of shopping centres and educational venues, Winston-Salem provides a dynamic travel experience for all. Whether you're attending a conference or enjoying a day out with family, the city's welcoming atmosphere and engaging sites make it a must-visit destination.
  • Kernersville: Located a mere 16.1km from Winston-Salem, Kernersville is a charming city that invites outdoor enthusiasts and families to enjoy its scenic beauty. Known for its parks and recreational opportunities, travelers can explore local lakes and enjoy the area's natural landscapes. The city features a range of entertainment options, including an arena and shopping malls. With a strong sense of community and educational institutions nearby, Kernersville is ideal for those seeking a peaceful getaway with plenty of opportunities for adventure and relaxation.
  • Clemmons: Just 14.5km from Winston-Salem, Clemmons is a delightful city that offers a blend of outdoor activities and urban charm. Perfect for family outings, visitors can enjoy urban parks, picturesque lakes, and various shopping centres. With a focus on community and education, Clemmons provides ample opportunities for family bonding and exploration. The city's friendly atmosphere and accessible amenities make it a fantastic destination for those looking to immerse themselves in both nature and city life.

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 simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can often result in significant savings. To discover the ideal Vrbo property that suits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the perfect fit for your getaway.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers you a user-friendly area to plan new adventures, resume your previous arrangements, or manage your travel itineraries. You’ll discover your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-ca/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 a few of the reasons to vacation in Winston-Salem. Renowned for its sporting events, shopping and forests, this city welcomes all visitors. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in Winston-Salem

Are you hoping to discover attractions to visit during your stay? Venture out of your vacation home and check out everything that makes Winston-Salem a fun place to get away. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 adventure or just want to spend some time taking in the scenery, Winston-Salem is a great place to get outside. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • 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)

Transportation 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 center. If you can't find a flight that's convenient for your trip, you could also fly into Piedmont Triad Intl. Airport (GSO), 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 vacation rental?
When considering a vacation rental in Winston-Salem, a fantastic area to stay is the historic district of Old Salem. This charming neighbourhood offers a unique glimpse into the Moravian culture and features beautifully preserved 18th-century buildings. One of the highlights in Old Salem is the Old Salem Museums & Gardens, which provides an immersive experience into the region's history and traditions. The area boasts a variety of vacation rental properties, appealing to those who appreciate a blend of historic charm and modern convenience.

Another excellent option is the downtown area, which is vibrant and full of life. Here, visitors can enjoy the arts scene, with attractions such as the Southeastern Centre for Contemporary Art (SECCA) and the Reynolda House Museum of American Art, both of which are within easy reach. Downtown Winston-Salem has a good selection of vacation rentals, suiting different tastes and budgets, making it a convenient base for exploring the city's cultural offerings and dining options.

For those who enjoy a more suburban feel, the Reynolda Village area is ideal. This picturesque neighbourhood is known for its lovely gardens and the stunning Reynolda House, which is surrounded by beautifully landscaped grounds. The village also features charming shops and cafes, superb for leisurely strolls. Properties here tend to be spacious and family-friendly, providing a peaceful retreat while still being close to the main attractions of the city.
How much does it cost to rent a vacation home in Winston-Salem?
Prices for vacation 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 travelling 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.
Are there any discounts for Winston-Salem vacation 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 vacation rental accomodation in Winston-Salem?
In Winston-Salem, vacation houses are the most popular rental option, with around 153 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation, making them ideal for families and groups looking for comfort during their stay. Additionally, there are about 63 apartments scattered across the city, often located near attractions like the Reynolda House Museum of American Art and the historic Old Salem. These apartments generally offer convenient amenities, including kitchen facilities and living areas. For those seeking a more quaint experience, approximately 16 cottages and 16 condos are available, providing a charming atmosphere and added privacy. While cabins are less common, several can be found in the surrounding natural areas, great for those wanting to immerse themselves in the outdoors.
Are there any family house rentals in Winston-Salem?
In Winston-Salem, North Carolina, there are numerous family-friendly vacation rentals, with around 122 options available throughout the city. The neighbourhoods of Old Salem and Reynolda Village are particularly appealing for families, each offering a unique blend of history and outdoor activities.

Old Salem is known for its charming historic district, where visitors can find homes with spacious living areas, fully equipped kitchens, and outdoor patios ideal for family gatherings. This area is close to attractions like the Old Salem Museums & Gardens, allowing families to immerse themselves in the region's rich history.

Meanwhile, Reynolda Village features larger properties that often boast amenities such as playrooms, fenced yards, and proximity to the picturesque Reynolda Gardens. This locale is superb for families who enjoy outdoor activities and exploring nature, with nearby walking paths and beautiful gardens to wander through.
Can I rent a vacation home with a pool or hot tub in Winston-Salem?
In Winston-Salem, there are several vacation 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 district and the scenic areas surrounding Hanes Park.
Can I find long-stay vacation rentals in Winston-Salem?
A long-stay vacation 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 feature spacious backyards, allowing pets to roam freely, along with amenities such as fully equipped kitchens, comfortable living areas, and often outdoor spaces like patios or decks for relaxation after a day of exploring.

The historic district of Old Salem is particularly charming, with its cobblestone streets and preserved Moravian architecture. Here, visitors can find rentals that combine modern comforts with a touch of history. Additionally, the nearby Reynolda Gardens offers expansive green spaces and walking trails, great for daily walks with pets while enjoying the beautiful scenery. See all pet-friendly rentals in Winston-Salem.
Are there any remote work vacation rentals in Winston-Salem?
In Winston-Salem, North Carolina, there are numerous vacation rentals suitable for remote work, with around 217 options available. Many of these properties are equipped with dedicated workspaces, including desks and ergonomic chairs, as well as high-speed Wi-Fi, ensuring a productive environment. Travellers can expect amenities like laptop workspaces and computer monitors in various accommodations, making it easy to set up a functional home office. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winston-Salem vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation 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 vacation rental?
The best time to visit Winston-Salem for a vacation rental is during the peak season from July to September. This lively period attracts visitors eager to immerse themselves in the rich culture and history of the region, with July being particularly popular. During these months, the warm temperatures (averaging mid to high 30s Celsius) create superb conditions for outdoor activities, festivals, and exploring the city's vibrant arts scene.

Winston-Salem offers an array of attractions, including the renowned Reynolda Gardens and the historic Old Salem, where travellers can delve into the area's fascinating Moravian heritage. The summer months are bustling with energy, making it an excellent time for those who enjoy socialising and engaging in community events.

For those looking for a more tranquil experience, consider visiting in December. This month provides a unique charm with fewer crowds, allowing you to savour the festive atmosphere while enjoying the city's vacation decorations and local events. You'll find that winter in Winston-Salem has its own appeal, with milder temperatures (averaging around 5 to 10 degrees Celsius) making it comfortable for sightseeing and leisurely strolls.
How early should I book a Winston-Salem vacation rental?
Book your Winston-Salem vacation 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 vacation 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 explore a variety of attractions that reflect the city's rich history and culture. The historic Old Salem area offers a glimpse into Moravian life with its preserved buildings and interactive exhibits. Vacation rentals in this neighbourhood provide easy access to charming shops and traditional eateries.

The Reynolda House Museum of American Art, located in the Reynolda Village, is another highlight, showcasing a significant collection of art within a beautiful estate setting. Nearby, the Reynolda Gardens offers picturesque walking paths and horticultural displays, making it a lovely spot for relaxation.

For those interested in the arts, the Downtown Arts District is home to galleries, theatres, and the iconic Hanesbrands Theatre, where visitors can catch live performances. Properties in this area often feature modern amenities and are close to a vibrant dining scene.
Can I change or cancel my Winston-Salem home rental booking on Vrbo?
To find Winston-Salem vacation 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 vacation 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.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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