Holiday houses in Winston-Salem

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Top-rated holiday rentals in Winston-Salem

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A modern living area is showcased, featuring a leather sofa with a decorative throw. Glass block windows allow natural light to enter, illuminating the space. Two side tables flank the sofa, while a large area rug adds texture to the hardwood floor.
Apartment in Winston-Salem
4.97 out of 5 average rating, 105 reviews

The Foothills in Downtown WS! Renovated | King Bed

Your downtown getaway awaits at the SUMMIT @ West End! Walk to endless restaurants, bars, shops & entertainment throughout beautiful, downtown Winston! Relax in our fully renovated space, designed with comfort & creativity in mind. Enjoy on-site parking & laundry, deluxe coffee/tea station, premium KING mattress & linens, smart TVs in living room & bedroom, high-speed Wi-Fi & more! 3 min to Millennium Center 5 min to Wake Forest Baptist Health 7 min to LJVM 8 min to Novant Health 8 min to WFU

Guest favourite
The bungalow features a welcoming facade with white siding and a well-maintained front yard, showcasing greenery and flowering bushes. A wooden walkway leads to the front door, framed by large windows and a subtle awning. A chimney peeks from the roof, enhancing the charm of the home.
Home in Ardmore
4.92 out of 5 average rating, 111 reviews

Single Family Ardmore 3 min to Wake Forest Hosp.

2 BR Bungalow in Historic Ardmore District, 8 min walk to Wake Forest Hospital and conveniently located 5 min from Starbucks, Whole Foods and Publix. Small well behaved dogs are welcome with prior approval. It is also a short stroll to Ardmore coffee shop, ice cream, Carlisles pub, Arthur’s diner, famous PB’s hot dogs and burgers, groceries. We offer special monthly rates for anyone staying 30 days or longer for $2750 a month. Please message us if you are looking to rent for a month or longer

Top Guest favourite
A spacious suite features a large bed with decorative pillows and a patterned throw. A dresser and chair are positioned near a window, allowing natural light to fill the area. A television and a small table are present, along with a comfortable seating arrangement.
Guest suite in Winston-Salem
4.98 out of 5 average rating, 330 reviews

Private, Peaceful, Green Hideaway 6 Minutes to WFU

Just minutes from Wake Forest, we have a completely remodeled this very special place. We have often stood at the huge windows of this ground level space and watched mother deer with their fawns play in the yard. Your home away from home is at the end of an already quiet cul-de-sac so traffic noise is zero. Your suite is completely private with its own ground level entrance. Your kitchen has a full size sink, an induction stove, fridge, with all your cookware, dishes. New bath with tub.

Superhost
A comfortable living room features a light-colored sofa set with decorative cushions. A central ottoman sits atop a soft area rug. Large windows allow natural light to brighten the space, complemented by the soft illumination from a ceiling fan. Potted plants add a touch of greenery.
Condo in Winston-Salem
4.9 out of 5 average rating, 467 reviews

Sanctuary – 1bedroom & 1bathroom

My modern and convenient condo located in the heart of Winston-Salem’s shopping district will provide you with a 1 bedroom & bathroom space. The condo is professionally furnished and cleaned to provide a 5 star experience. Basic appliances provided (microwave, kitchen appliances, washer & dryer, dishwasher, Keurig). Very spacious with patio furniture for extra relaxation! You can also enjoy the community pool and gym. This space is NOT shared. Guests have the entire space to themselves.

Guest favourite
The main bedroom features a sizable bed with a dark gray throw and neatly arranged towels. Two bedside lamps provide soft illumination beside the bed. The room is complemented by two framed artworks, and a bathroom with glass door access is visible in the background.
Home in Winston-Salem
4.96 out of 5 average rating, 206 reviews

Beautiful 2 BR home with Office and Game Room

This beautifully decorated 2 bedroom home, part of a duplex, comes with high-speed Internet and Wi-Fi. It includes an office and a game room. It is near shopping, hospitals, and the rest of the Winston-Salem scene. The kitchen has all the tools needed to prepare your favorite meals. The TV in the living room includes Disney+. Everything except the game room is on the main level. The back deck is ready for hosting a barbecue, with a view of the backyard and adjoining green space.

Guest favourite
A two-story brick home is framed by manicured greenery and stone steps leading to the entrance. A spacious front porch, bordered by white railings, provides a welcoming area to enjoy the outdoors. The home features large windows that allow natural light to illuminate the façade.
Home in Winston-Salem
4.91 out of 5 average rating, 313 reviews

Historic Beauty: 5BR Home with Yard Near Hospital

This is a beautiful home, lovingly renovated to retain the original 1920s charm and preserve history, while including modern updates and conveniences. It is perfectly located in the heart of Winston Salem- only a few blocks from Wake Forest Baptist Hospital and less than a mile from downtown. Despite the city location, it features a 3 car garage and over 0.3 acres of lot space in the form of a great backyard. Additionally, it sits across the street from beautiful Hanes Park.

Top Guest favourite
A spacious bathroom features a large jetted tub set against bay windows, providing natural light. Dual sinks are positioned on a granite countertop, while a potted plant adds a touch of greenery. Black and white patterned flooring contrasts with the light-colored walls.
Guest suite in Winston-Salem
4.95 out of 5 average rating, 192 reviews

Entire COZY Unit - 3 min walk to WFU.

Welcome to your cozy - little nest. Please keep in mind that this unit is attached to our house (we shared a wall - different entrance). Everything showed in the pictures will be all yours (Master bedroom, Study room - living room Space, and an extraordinary bathroom). When staying at our place, you are: - 5 min walk to WFU Campus. - 5 min drive to Downtown. - 3 min drive to Stadiums and Restaurants. - 10min drive to Wake Forest Baptist Hospital. - Reynolda House museum.

Guest favourite
A cozy bedroom is presented, featuring a spacious bed adorned with a rust-colored quilt. A decorative lamp casts light beside a dark wood nightstand, accentuated by sculptural art pieces on display. A soft texture of a woven rug completes the inviting atmosphere.
Apartment in Winston-Salem
4.95 out of 5 average rating, 312 reviews

West Salem Art Hotel, "Art"partment #1

Welcome to the West Salem Art Hotel! This eclectic and beautiful apartment is located in a 1931 historic brick building only 1 mile from Downtown Winston-Salem! All the conveniences of staying JUST on the outskirts in Historic West Salem, without all the city noise, AND located in the middle of a peaceful urban garden! We are minutes away from the best eateries/entertainment W-S offers! Private, unique, and clean.

Guest favourite
The exterior of the cabin showcases a charming wooden facade, featuring a spacious balcony with wooden railings. Warm lights illuminate the entryway, creating a welcoming ambiance in the forested surroundings. A grassy area is visible in front of the cabin, emphasizing the natural setting.
Cabin in Winston-Salem
4.98 out of 5 average rating, 204 reviews

The Blue Door Cabin

This tiny cabin is brand new and nestled just inside the woods, but only 1/2 mile from I-74 and only 10 min. to downtown Winston Salem, NC. This little cabin was built just for Airbnb guests, it has granite tops, stained concrete floors, a beautiful tiled/stone shower, and will surely help you unwind and enjoy your stay in this delightful space!

Top Guest favourite
A view from the loft captures a vibrant urban landscape, featuring a green park area bordered by modern buildings. Vehicles are parked along the neatly paved roads, while pedestrians can be seen enjoying the open space under a clear blue sky.
Loft in Downtown Winston-Salem
4.99 out of 5 average rating, 105 reviews

Lovely 1 bedroom loft in Downtown, Winston-Salem

A 1930's building remodeled as a unique loft located in the heart of Wake Forest's Innovation Quarter. Walking distance from a variety of Winston-Salem's best local restaurants, bars, coffee shops, and entertainment. Plenty of natural light with some of Downtown Winston's best views. Stocked kitchen, full bathroom, and Wi-Fi included.

Guest favourite
A bright living room features a cozy seating arrangement with a light-colored sofa and two blue armchairs. A wooden coffee table rests on a soft area rug, while a wall clock adds a decorative touch. Natural light streams in through the window, enhancing the space.
Home in Sunnyside
4.93 out of 5 average rating, 103 reviews

Modern Craftsman *Pet-Friendly* Near Downtown

Newly renovated craftsman bungalow in a quiet historic neighborhood in Winston Salem. Casa Patria is conveniently located to major highways, shops, restaurants & entertainment. Just 4 min from UNC school of the arts, 7 minutes from Downtown, Atrium Baptist Hospital, Forsyth Medical Center, and 15 mins from Wake Forest University.

Guest favourite
An inviting living area features a plush blue sofa adorned with patterned cushions. A custom Japanese wall adds a unique touch, while a flat-screen TV is mounted on the wall. The open layout connects seamlessly to a modern kitchen with a dining area.
Apartment in Winston-Salem
4.79 out of 5 average rating, 114 reviews

Zen 1-Bed Oasis in Historic Downtown Winston-Salem

Welcome to Your Home Away from Home! Nestled in the heart of Winston-Salem's vibrant North Central neighborhood, our cozy 1-bedroom apartment offers the perfect blend of comfort and convenience. Whether you're visiting for business or leisure, this cozy retreat is just moments away from downtown Winston-Salem best attractions.

Popular amenities for Winston-Salem holiday rentals

When is the best time to visit Winston-Salem?

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Frequently Asked Questions

  • What are the best places to stay in Winston-Salem?

    Winston-Salem has popular stays near downtown, the Historic West End, and Ardmore neighborhoods, known for tree-lined streets and easy access to arts, dining, and local attractions. Many guests look for accommodations with outdoor spaces or walkable surroundings to enjoy the city’s relaxed character.

  • What are the best things to do in Winston-Salem with kids?

    Families often explore interactive museums, local parks, and playgrounds, enjoying hands-on experiences related to history or nature. The city's gardens, science centers, and seasonal festivals are frequently suggested for children.

  • What are some of the best things to do in Winston-Salem?

    Explore Old Salem Museums & Gardens for historic interpretation, stroll the Reynolda Gardens, and discover galleries in the downtown arts district. Many visitors also enjoy tasting local cuisine and attending community events.

  • How is the weather in Winston-Salem?

    Winston-Salem has mild winters around 30–49°F (-1–10°C) and warm, humid summers near 69–89°F (21–31°C), with rainfall fairly evenly spread throughout the year. Spring and autumn feature moderate temperatures and blooming landscapes.

  • When is the best time to visit Winston-Salem?

    Spring and autumn are frequently suggested for their comfortable temperatures and local festivals. These seasons bring blooming gardens and outdoor events across Winston-Salem.

  • What are the best places to visit in Winston-Salem?

    Popular sites include Old Salem Museums & Gardens, Reynolda House Museum of American Art, and the Southeastern Center for Contemporary Art. Neighborhood markets and local parks add to the city's welcoming atmosphere.

  • What are some hiking trails in Winston-Salem?

    Stroll the nature paths at Reynolda Gardens, explore wooded trails in Salem Lake Park, or visit historic walking routes at Tanglewood Park just outside the city. Trails here feature forest views and opportunities for birdwatching.

  • What are some family activities we can do in Winston-Salem?

    Families can visit interactive museums, participate in outdoor activities at neighborhood parks, and join hands-on workshops that highlight local crafts or traditions. Community festivals often feature music, food, and kid-friendly events.

  • What are some of the best day trip ideas from Winston-Salem?

    Plan a day exploring the wine country around Yadkin Valley, tour nearby nature preserves, or discover mountain trails just outside the city. Small towns surrounding Winston-Salem have historic districts and vibrant local markets.

  • Are there any pet friendly accommodations available in Winston-Salem?

    Many hosts in Winston-Salem welcome pets, especially around neighborhoods like Ardmore, West End, and downtown. Several parks and green spaces nearby make outings with your dog easy and enjoyable.

  • What are some local tips for visiting Winston-Salem?

    Enjoy walking tours in historic districts, arrive early at local markets for fresh goods, and try seasonal flavors at neighborhood bakeries. Locals also suggest checking event calendars for pop-up concerts and art shows.

  • What is Winston-Salem known for?

    Winston-Salem is recognized for its art scene, historic districts, and tobacco industry heritage. The city has strong ties to universities and offers interpretation of regional history, including periods of enslavement at some historic sites.

  • What are the best hidden gems to explore in Winston-Salem?

    Winston-Salem has vibrant murals in the downtown arts district, tucked-away coffee shops around West End, and small galleries featuring local artists. Guests often enjoy discovering public gardens and quiet walking trails in residential neighborhoods.

  • What are the best foods to try in Winston-Salem?

    Sample locally made Moravian cookies, Carolina-style barbecue, and scratch-made biscuits. Farm-to-table restaurants highlight seasonal ingredients, and artisanal bakeries create treats inspired by the city’s heritage.

  • What should I bring for a trip to Winston-Salem?

    Pack comfortable walking shoes, an umbrella or light rain jacket, and layers for changing temperatures. In warmer months, sunscreen and reusable water bottles are helpful for exploring outdoor sites.

  • What is the nightlife in Winston-Salem like?

    Nightlife in Winston-Salem includes downtown brewpubs, intimate venues for live music, and lively patios around the arts district. Many visitors enjoy creative cocktails and community gatherings into the evening.

  • What are the most popular events or festivals in Winston-Salem?

    The National Black Theatre Festival draws theatergoers in late summer, and RiverRun International Film Festival lights up the film scene in spring. Community street fairs, art walks, and music events are frequently suggested, especially during warmer months.

  • Are there family friendly vacation rentals in Winston-Salem?

    Winston-Salem has family-friendly vacation rentals, especially in the Ardmore, West End, and Buena Vista neighborhoods. Many stays feature spacious layouts or outdoor areas, creating comfortable spaces for families to relax after a day exploring.

Quick stats about holiday rentals in Winston-Salem

  • Total holiday rentals

    Explore 1,030 holiday rentals in Winston-Salem

  • Nightly prices starting at

    Winston-Salem holiday rentals start at $29 AUD per night before taxes and fees

  • Verified guest reviews

    Over 47,520 verified reviews to help you choose

  • Family-friendly holiday rentals

    580 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 410 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    640 properties have a dedicated workspace

  • Wi-Fi availability

    1,010 of Winston-Salem holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Winston-Salem rentals

  • 4.8 Average rating

    Winston-Salem stays are highly rated by guests—averaging 4.8 out of 5!

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