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 recreational area features a spacious pool table centered beneath three pendant lights. Surrounding walls display various signs and memorabilia, including a dartboard. Two high-backed chairs are positioned at the side, and natural light filters in through a window with closed blinds.
Guest suite in Winston-Salem
4.98 out of 5 average rating, 625 reviews

The Man Cave

The Man Cave is close to the highway. It is minutes away from downtown Winston-Salem, Wake Forest University, Hanes Mall, and Baptist Hospital. You'll love the place because of its private entrance and great "Man Cave" amenities... King bed, wi-fi, pool table, dartboard, 50" TV & DirecTV satellite cable, Keurig machine, full kitchen, washer/dryer, etc. Don't let the name fool you... It is good for a couples get away, solo adventurers, and business travelers looking for a unique experience.

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
4.99 out of 5 average rating, 313 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 living area features hardwood flooring and natural light from multiple windows. A comfortable sofa with decorative pillows faces a simple coffee table and a modern TV stand. A bright accent chair adds a pop of colour, creating a welcoming space.
Home in Winston-Salem
4.97 out of 5 average rating, 116 reviews

House in Washington Park, w/NC beer tasting

I love my neighborhood! Brand New Location for me! Relax with the family at this peaceful place to stay! If you are just passing through or traveling for work, this is the perfect place for you! Located in Washington Park (which is just 2 miles from Downtown), you will have easy access to all Winston has to offer! I also own Hoots Beer Company, and I will be happy to give you a beer tasting! If you see a concert you want to attend at my place, a free ticket is on me! Side note: NO PARTIES!

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, 461 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.

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, 172 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 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, 184 reviews

Entire COZY Unit - 3 min walk to WFU.

Welcome to your cozy - little net. 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: - 3 min drive (10min walk) to WFU Campus. - 5 min drive to Downtown. - 3 min WALK to Stadiums and Restaurants. - 10min drive to Wake Forest Baptist Hospital. - Reynolda House museum.

Top guest favorite
A comfortable green sofa is positioned opposite a wooden coffee table, which holds several magazines. Above the sofa, framed photographs adorn the wall, while a floor lamp provides lighting. The space is unified with rich wooden flooring and an open layout leading to an adjacent room.
Condo in Winston-Salem
4.97 out of 5 average rating, 179 reviews

Old Salem Getaway - Visit DTWS via the Strollway

We love our comfy third floor condo with elevator access. Whether you are in town for business or pleasure, this condo fits the bill. Walk to Old Salem, UNCSA, and Salem College. Jog or bike Salem Creek trail, which is at our doorstep. Stroll through Old Salem on your way to downtown’s amazing eateries and breweries. Close by are Wake Forest University, WSSU and downtown Winston-Salem, and hospitals - this condo is central to anywhere in the Winston-Salem area.

Top guest favorite
Cottage in Winston-Salem
4.98 out of 5 average rating, 109 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.

Top guest favorite
An inviting kitchen area features modern appliances, including a stainless steel refrigerator and microwave. A granite-topped island with two black stools provides space for dining or preparation. Wooden shelves showcase dishware against a white tiled backsplash, complemented by warm wood cabinetry and natural light from a window.
Guest suite in Ardmore
4.98 out of 5 average rating, 109 reviews

Bright and refreshing apartment in Ardmore

Our studio apartment is located in the heart of Historic Ardmore. We are 5 minutes from both Novant and Atrium (Baptist) hospitals, 7 minutes from downtown Winston Salem and 10 minutes from Wake Forest University. The apartment is totally private, quiet and furnished to be comfortable for either a short or long term stay! Enjoy our safe, walkable neighborhood as well as easy and close access to the major highways.

Guest favorite
A cozy bedroom features a wooden bed with a light blue bedding set. A ceiling fan illuminates the space, complemented by two bedside lamps. A piece of artwork depicting birds adds a touch of nature, while natural light enters through a small window.
Condo in Ardmore
4.89 out of 5 average rating, 293 reviews

Charming quiet condo all to yourself

This is a cozy non pet condo for two. Perfect for TRAVEL NURSE or extended stay hospital visits. Next door to Novant Health care and 1.5 miles from Baptist Hospital. Grocery and restaurants in walking distance. Will meet new guests in person. A few easy steps to the lower level then flat up to the door. Non-smoking. No pets. Contact host in message box for availability.

Guest favorite
A modern kitchen is presented with white cabinetry and a spacious island featuring a wooden cutting board. Built-in appliances include a dishwasher and a stove. Natural light enters through large windows, while a small dining area with wooden chairs is visible in the adjacent room.
Home in Winston-Salem
4.95 out of 5 average rating, 112 reviews

Peaceful house minutes from Wake Forest University

If you are visiting Winston-Salem, why not stay in a cozy home, tucked away on a quiet, dead-end street? No need to sacrifice convenience, as it is situated only 2 miles from Wake Forest University, 5-6 miles from the heart of Winston-Salem. You are also within walking distance of Historic Bethabara, a great place to explore that includes a nice walking trail.

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, 140 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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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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