Vacation rentals in Winston-Salem

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Top-rated vacation rentals in Winston-Salem

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

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Top guest favorite
A spacious living area features a light-colored sectional sofa adorned with decorative pillows. A wooden coffee table with a geometric pattern is positioned in front, complementing the beamed ceiling. A view of the kitchen area is visible through an archway, enhancing the open floor plan.
Home in Winston-Salem
5 out of 5 average rating, 225 reviews

The Zen Ranch - Spacious Layout with Modern Decor

1960s ranch style home on 2 acres with 2,400ft² interior. This home has been fully remodeled with a large open floor plan and all modern amenities and decor. With ample yard and patio space, large bedrooms, bonus room and 3 full bathrooms there is plenty of space to spread out. • Abundant Natural Lighting • Backyard w/ patio + fire pit + hammocks • Comfy Beds • Fully stocked Chefs Kitchen • Large Private Deck + BBQ grill • Indoor fireplace • 400Mps WiFi • 3 x 4K TVs w/ Disney, Netflix & Prime

Top guest favorite
A contemporary living area is highlighted by a plush, emerald green sofa adorned with yellow accent pillows. A sleek coffee table sits on a patterned rug, illuminated by natural light from nearby sliding glass doors. Modern decor includes a wall art piece and stylish lighting fixtures.
Home in Winston-Salem
4.96 out of 5 average rating, 102 reviews

Emerald Retreat - Central & Stylish - 2 BR/2 BA

Centrally located, yet away from the hustle and bustle is this contemporary styled condo ideal for families, couples and professionals with downtown, supermarkets, medical centers and great food all just mins away. Nestled within a leafy community, the condo features chic design, spacious living, a fully equipped kitchen, 2 beautiful bedrooms, 2 modern bathrooms and a private patio. You’ll be mins from Hanes Mall, Forsyth Tech, Novant and Wake Forest Medical Center, shops and many restaurants.

Guest favorite
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 favorite
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.

Top guest favorite
A vibrant outdoor space features several tables and umbrellas in blue, pink, and red shades. Green vines cascade from the second-floor balcony, complemented by a large red umbrella, creating a refreshing atmosphere. The textured white wall serves as a backdrop for this inviting area.
Apartment in Downtown Winston-Salem
4.96 out of 5 average rating, 189 reviews

K obscura

Historic loft in Downtown Winston Salem's Innovation Quarter. Located above Krankies Coffee near WFB Medical School and Bailey Park.Short walking distance to several restaurants and bars. This space has private entrance and patio. Includes gift card for coffee at Krankies. Note there is a train that passes by a few times a day and at night. We do allow pets but have a fee. Includes deep soaking tub, mini-kitchen and comfy king-size bed. Space is accessed via stairs. Parking included.

Top guest favorite
A charming 1920s era house is set against a backdrop of colorful autumn foliage. The house features a welcoming porch with stone accents, large front windows, and a well-maintained garden, creating an inviting exterior.
Home in Winston-Salem
4.98 out of 5 average rating, 130 reviews

Dragonfly: 1 Br Garden Apt Near WFU & Baptist Hosp

The "Dragonfly" is a spacious, peaceful 1BR garden terrace apartment (800 sq ft) in one of Winston-Salem’s most desirable neighborhoods. Just 1 mile from Baptist Hospital, 4 miles from Wake Forest University, and 10 minutes from downtown, this light-filled retreat is perfect for medical travelers, university visitors, couples, or small families. Features a king bed, washer/dryer, workspace with fast Wi-Fi, kitchenette, and private patio with garden views. Hi-chair & Packngo for families

Top guest favorite
Cottage in Winston-Salem
4.98 out of 5 average rating, 118 reviews

Sleepy Bee Cottage, simple charms, near WFU

It feels like the countryside within city limits on shared property with owners home. The cottage has views of the acre+ woodland behind and a garden in front. Beyond the property there is a Duke Power easement and a ravine. There is ample, well-lit parking and a fenced dog yard. There is a small seating area out front under the shade of a dogwood tree. Smoking is NOT allowed on the property. Additional fees will be charged for violation of this rule.

Guest favorite
A vibrant entrance hallway is adorned with a large floral mural painted in warm tones of orange, green, and blue. A modern dark door serves as the focal point. Soft lighting from a nearby wall sconce highlights the artistic elements, enhancing the space's unique character.
Hotel room in Winston-Salem
4.92 out of 5 average rating, 198 reviews

🌹Rose Room Apartment, West Salem Art Hotel

Welcome to the West Salem Art Hotel! This eclectic and beautiful apartment is in a 1931 historic brick building, a stone's throw from Downtown Winston-Salem and a 3-minute walk to Truist Ballpark! It is so close to downtown without all the city noise, and it is located in the middle of a peaceful urban garden! Free Parking! A short walk away from W-S's best eateries/entertainment! Private, unique, and Clean!

Top guest favorite
Cottage in Advance
5 out of 5 average rating, 231 reviews

Rocky Knoll Hideaway | Visit Family | Cozy Stay

Welcome to Rocky Knoll Hideaway — your peaceful home base for visiting family, relaxing, and recharging. Tucked among the trees, this cozy private cottage offers the perfect blend of quiet seclusion and convenient access to the area. Whether you’re here for a weekend visit, a holiday stay, or just a break from the busy pace of life, Rocky Knoll Hideaway offers a warm, welcoming place to land.

Top guest favorite
A single-family home features a light-colored exterior with blue shutters. A large, attached garage is visible, with a paved driveway leading to it. The front yard is well-maintained, showcasing shrubs and a tree with vibrant autumn foliage.
Home in Winston-Salem
4.93 out of 5 average rating, 212 reviews

"Deacon House" 3 bedrooms

Looking for a place to stay in Winston Salem? Check out this 1,315 sqft. single family home that has 3 bedroom and 2 full bath. It has its own driveway with 2 car garage attached and fenced in backyard, guest occupy the entire house except the attic. It is just a few minutes away from downtown, Wake Forest University, Reynolda Garden, LJVM coliseum, Starbucks and grocery stores.

Top guest favorite
A welcoming white house is set against a backdrop of lush greenery, featuring a gently sloping driveway. The entrance is framed by dark window shutters and flower planters, complemented by a large tree providing shade.
Home in Winston-Salem
5 out of 5 average rating, 120 reviews

THE GUEST HOUSE

Sophisticated comfortable elegance. Easy, charming and super comfortable! Quiet old neighborhood close to wake forest university, GRAYLYN, Reynolda Gardens, great restaurants, huge yard, delightful decor featuring local artists, luxury bedding, full kitchen, wifi, cable, outside deck lots of eating space,easy parking, screened in porch for morning coffee with birdsong.

Top guest favorite
A dining table is set with yellow napkins and plates, complemented by glassware and decor. In the background, a living area is visible with a TV, a cozy chair, and a small plant accenting the space. A workspace is arranged with a desk against the wall.
Apartment in Winston-Salem
4.99 out of 5 average rating, 147 reviews

Executive Escape

A well appointed and modern space for those looking for a home away from home. Wether you're visiting family and friends, or on assignment, this space has all you need while visiting Winston Salem. Located in a quiet and mature neighborhood, you'll find easy access to the local hospitals and WFU. Local shops, eateries and things to do also ...

Popular amenities for Winston-Salem vacation rentals

When is the best time to visit Winston-Salem?

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Avg. priceﺩ.ﺇ371ﺩ.ﺇ367ﺩ.ﺇ367ﺩ.ﺇ408ﺩ.ﺇ411ﺩ.ﺇ393ﺩ.ﺇ389ﺩ.ﺇ386ﺩ.ﺇ400ﺩ.ﺇ433ﺩ.ﺇ411ﺩ.ﺇ400
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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 vacation rentals in Winston-Salem

  • Total vacation rentals

    Explore 1,030 vacation rentals in Winston-Salem

  • Nightly prices starting at

    Winston-Salem vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 47,520 verified reviews to help you choose

  • Family-friendly vacation rentals

    580 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 410 rentals that welcome pets

  • Vacation 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 vacation 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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