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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Guest favorite
The kitchen features rustic wooden cabinetry and a large central island with matching wooden benches. Stainless steel appliances are included, with a microwave and stovetop visible. Pendant lights illuminate the space, creating a warm and welcoming atmosphere.
Cabin in West Salem
4.89 out of 5 average rating, 866 reviews

Log Cabin in the city

READ ENTIRE LISTING! NO PARTIES/ GATHERINGS. Only the guests on the reservation are allowed to be on my property. I WILL KICK YOU OUT AND CALL THE COPS. I DO NOT PLAY GAMES. The listing is the entire UPPER LEVEL of my log cabin, which is conveniently located less than a mile from Downtown Winston-Salem! The back yard is surrounded by woods and a privacy fence! Great place close to downtown. NO SMOKING of any kind allowed anywhere. Pots and pans are available. No salt and pepper or condiments

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, 310 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, 165 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, 182 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 single-family ranch home is showcased with a stone accent exterior, surrounded by well-maintained landscaping. A paved driveway leads to the entrance, while trees and flowering plants add natural beauty to the front yard.
Home in Winston-Salem
4.98 out of 5 average rating, 119 reviews

Elegant Pet Friendly Ranch close to everything!

Our sun filled updated 1950's single family ranch home in a quiet and beautiful neighborhood has all the comforts needed for a long or short stay. Fabulous location-just minutes to multiple universities, hospitals, historic sites and downtown Winston-Salem. Nearby are plenty of restaurants, shopping and recreational parks. Piedmont Triad Airport in Greensboro is 35 minutes away. ***ALLERGY ALERT*** I do have the house professionally cleaned but dogs and cats do stay here occasionally.

Top guest favorite
A spacious living area is highlighted by a comfortable gray sofa adorned with striped cushions. A wooden coffee table sits in front, with a colorful area rug beneath. Nearby, a dining table accompanied by chairs is visible, along with art pieces on the walls, enhancing the open ambiance.
Apartment in Downtown Winston-Salem
4.87 out of 5 average rating, 110 reviews

Luxury Downtown Loft

Enjoy a stylish experience at this centrally-located place. 3rd Floor urban loft in a secure, historic building in heart of downtown full of natural light, bright decor, and polished hardwood floors. Loft is just steps from Aperture theatre, 4th Street restaurants, the Stevens Center, and lots of shopping. Easy walk to everywhere downtown, and many ways to get to Wake quickly. Full of supplies and amenities - an oasis for business travel, vacation, or anything in between!

Guest favorite
The exterior of a charming efficiency apartment is shown, featuring a covered porch with a welcoming sign. Lattice work accents the porch, while a small stone path leads to the entry. Lush greenery surrounds the building, enhancing its inviting appearance.
Guesthouse in Germanton
4.96 out of 5 average rating, 517 reviews

Mel’s country cottage. Country life near the city.

Private detached effeciency apartment in a country setting near WinstonSalem. Queen bed, kitchenette with sink and essentials, sofa, smart TV, full bath, covered porch. Relax by the creek or enjoy nature walks. Watch the occasional deer & other wildlife. Use the grill or fire pit at your leisure. Pets welcome. Local restaurant & convenient store 1 min. away. Close to many tourist destinations- Hanging Rock, Winston Salem, Pilot Mt. Belews Creek power station.

Top guest favorite
Cottage in Winston-Salem
4.98 out of 5 average rating, 102 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, 108 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.

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, 208 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.

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, 292 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
The living room features hardwood floors and light green walls, providing a bright and airy feel. A leather couch faces a coffee table, while a small TV is positioned on a wooden stand. Natural light enters through a window beside the front door.
Apartment in Downtown Winston-Salem
4.93 out of 5 average rating, 640 reviews

Urban oasis in downtown W-S; sparkling clean

Top unit of a three-family house, this 1000 sq ft. 2 bedroom, 1 bath apartment is in the heart of downtown Winston-Salem. Please review our house rules before you book. It is an ideal location two blocks away from all of the action of Fourth and Trade Streets, tucked into a funky, tree-lined neighborhood that is quiet and private.

Popular amenities for Winston-Salem vacation rentals

When is the best time to visit Winston-Salem?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$21,110 GYDG$20,901 GYDG$20,901 GYDG$23,200 GYDG$23,409 GYDG$22,364 GYDG$22,155 GYDG$21,946 GYDG$22,782 GYDG$23,618 GYDG$22,364 GYDG$21,528 GYD
Avg. temp4°C6°C10°C15°C20°C24°C26°C25°C22°C16°C10°C6°C

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 1,000 vacation rentals in Winston-Salem

  • Nightly prices starting at

    Winston-Salem vacation rentals start at G$4,180 GYD per night before taxes and fees

  • Verified guest reviews

    Over 46,400 verified reviews to help you choose

  • Family-friendly vacation rentals

    560 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 390 rentals that welcome pets

  • Vacation rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    620 properties have a dedicated workspace

  • Wi-Fi availability

    980 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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