Winston-Salem holiday rentals

We found 575 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Winston-Salem by choosing from 209 houses, 86 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:11 Dec - 18 Dec

Living area
Private kitchen
Interior
Interior
Exceptional
(6 reviews)

Beautiful 1800’s Cabin with newly renovated addition. WFU only 7 miles away.

Winston-Salem

8% off
AU$4,668
for 7 nights, 1 cabin
AU$667 per night
includes taxes & fees
Beautiful 1800’s Cabin with newly renovated addition. WFU only 7 miles away.
Study
Grand Room at night!
Kitchen
Master Balcony at night
Exceptional
(16 reviews)

Stunning Penthouse 15-B Located In Historic Market Square.

High Point

8% off
AU$10,237
for 7 nights, 1 home
AU$1,462 per night
includes taxes & fees
Stunning Penthouse 15-B Located In Historic Market Square.
Living area
Interior
Private kitchen
Interior
Exceptional
(12 reviews)

Luxurious Cape Cod in Emerywood - Minutes to Furniture Market & HP University

High Point

7% off
AU$4,500
for 7 nights, 1 home
AU$643 per night
includes taxes & fees
Luxurious Cape Cod in Emerywood - Minutes to Furniture Market & HP University
Exterior
Private kitchen
Interior
Living area
Very good
(6 reviews)

Charming 4-bedroom house with AC and WiFi in wonderful Winston-Salem

Winston-Salem

7% off
AU$5,453
for 7 nights, 1 home
AU$779 per night
includes taxes & fees
Charming 4-bedroom house with AC and WiFi in wonderful Winston-Salem
Private kitchen
Pool
Terrace/patio
Living area
Wonderful
(27 reviews)

Private & Spacious 4BR w/ Heated Pool, Hot Tub & Fire Pit - Near HPU & Market

High Point

5% off
AU$5,343
for 7 nights, 1 home
AU$763 per night
includes taxes & fees
Private & Spacious 4BR w/ Heated Pool, Hot Tub & Fire Pit - Near HPU & Market
Living area
Dining
Room
Exterior detail
Exceptional
(13 reviews)

Spacious Home + 6 Beds + Huge Fenced Yard Near Wake Forest University + Hospital

Winston-Salem

7% off
AU$2,729
for 7 nights, 1 home
AU$390 per night
includes taxes & fees
Spacious Home + 6 Beds + Huge Fenced Yard Near Wake Forest University + Hospital
Exterior
Living area
Room
Dining
Exceptional
(16 reviews)

Charming 3-bedroom cottage centrally located to enjoy High Point.

High Point

7% off
AU$1,827
for 7 nights, 1 cottage
AU$261 per night
includes taxes & fees
Charming 3-bedroom cottage centrally located to enjoy High Point.
Exterior
Private kitchen
Property grounds
Interior
Exceptional
(10 reviews)

Spacious 4-bedroom house in charming Winston-Salem with WiFi and fenced in yard.

Winston-Salem

10% off
AU$3,299
for 7 nights, 1 home
AU$471 per night
includes taxes & fees
Spacious 4-bedroom house in charming Winston-Salem with WiFi and fenced in yard.
Interior
Living area
Living area
Room
Wonderful
(35 reviews)

Charming Ardmore Home minutes from hospitals/I-40

Winston-Salem

11% off
AU$2,270
for 7 nights, 1 home
AU$324 per night
includes taxes & fees
Charming Ardmore Home minutes from hospitals/I-40
Living area
Dining
Interior
Living area
Exceptional
(11 reviews)

Cheerful cottage w/work space near hospitals

Winston-Salem

7% off
AU$1,750
for 7 nights, 1 home
AU$250 per night
includes taxes & fees
Cheerful cottage w/work space near hospitals
Room
Private kitchen
Outdoor dining
Living area
Exceptional
(7 reviews)

Beautiful Farm and Barndo Loft in Kernersville with WiFi and AC

Kernersville

8% off
AU$1,413
for 7 nights, 1 home
AU$202 per night
includes taxes & fees
Beautiful Farm and Barndo Loft in Kernersville with WiFi and AC
Private kitchen
Living area
Dining
Exterior
Excellent
(13 reviews)

Cozy 2BR King Bed Sleeps 6 Near Hospital & Wake Forest

Winston-Salem

7% off
AU$1,603
for 7 nights, 1 home
AU$229 per night
includes taxes & fees
Cozy 2BR King Bed Sleeps 6 Near Hospital & Wake Forest
Kitchen open to dining room table seats 6.
Muse at Graylyn.
Entrance to Graylyn property.
Living room
Exceptional
(91 reviews)

Walking distance to Reynolda House and Gardens. Close to Wake Forest University

Winston-Salem

8% off
AU$5,012
for 7 nights, 1 home
AU$716 per night
includes taxes & fees
Walking distance to Reynolda House and Gardens. Close to Wake Forest University
Room
Private kitchen
Living area
Exterior
Exceptional
(29 reviews)

Updated 1BR cottage on private acre+ lot

Winston-Salem

7% off
AU$915
for 7 nights, 1 home
AU$131 per night
includes taxes & fees
Updated 1BR cottage on private acre+ lot
Interior
Private kitchen
Exterior
Dining
Very good
(15 reviews)

3 King Beds | XL TVs | Near Hospital, College & DT

Winston-Salem

5% off
AU$1,303
for 7 nights, 1 home
AU$186 per night
includes taxes & fees
3 King Beds | XL TVs | Near Hospital, College & DT
Exterior
Living area
Room
Private kitchen
Exceptional
(7 reviews)

Cozy Cottage minutes to Downtown

Winston-Salem

7% off
AU$1,842
for 7 nights, 1 cottage
AU$263 per night
includes taxes & fees
Cozy Cottage minutes to Downtown
Springtime garden
Nighttime under the stars
Interior
Private kitchen
Exceptional
(64 reviews)

Elegant Pet Friendly Ranch Home close to everything!

Winston-Salem

8% off
AU$2,588
for 7 nights, 1 home
AU$370 per night
includes taxes & fees
Elegant Pet Friendly Ranch Home close to everything!
Living area
Property grounds
Exterior detail
Living area
Exceptional
(42 reviews)

Home in a nice High Point Neighbourhood

High Point

5% off
AU$1,531
for 7 nights, 1 home
AU$219 per night
includes taxes & fees
Home in a nice High Point Neighbourhood
Exterior
Room
Private kitchen
Interior
Exceptional
(12 reviews)

Luxury Cottage. 2 King Suites. Walk Downtown & Old Salem

Winston-Salem

8% off
AU$3,381
for 7 nights, 1 cottage
AU$483 per night
includes taxes & fees
Luxury Cottage. 2 King Suites. Walk Downtown & Old Salem
Living Room
Property grounds
Property grounds
Living area
Exceptional
(76 reviews)

Historic Craftsman bungalow near Winston Salem, wineries and mountain activities

Rural Hall

11% off
AU$1,597
for 7 nights, 1 home
AU$228 per night
includes taxes & fees
Historic Craftsman bungalow near Winston Salem, wineries and mountain activities
Terrace/patio
Private kitchen
Bathroom
Dining
Exceptional
(17 reviews)

Modern, Comfortable and Cozy Large Apartment

Lewisville

7% off
AU$1,877
for 7 nights, 1 apartment
AU$268 per night
includes taxes & fees
Modern, Comfortable and Cozy Large Apartment
Exterior detail
Room
Living area
Exterior
Wonderful
(142 reviews)

Guest suite in Winston Salem

Winston-Salem

7% off
AU$738
for 7 nights, 1 apartment
AU$105 per night
includes taxes & fees
Guest suite in Winston Salem
Living area
Private kitchen
Living area
Room
Exceptional
(8 reviews)

Charming 4-bedroom house with AC and WiFi in Winston-Salem

Kernersville

7% off
AU$1,972
for 7 nights, 1 home
AU$282 per night
includes taxes & fees
Charming 4-bedroom house with AC and WiFi in Winston-Salem
Room
Living area
Exterior
Interior
Exceptional
(12 reviews)

Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem

Winston-Salem

8% off
AU$1,870
for 7 nights, 1 cabin
AU$267 per night
includes taxes & fees
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

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:

  • 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)
  • Grandover Resort West Course (21.5 mi / 34.6 km)
  • Grandover Resort East Course (21.6 mi / 34.8 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.
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.

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