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, 861 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 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, 615 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, 305 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, 158 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, 174 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, 116 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 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, 175 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.

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, 514 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
A covered patio area features a set of two chairs and a small table beneath an overhang. Double doors lead into the guest suite, while sunlight casts intricate shadows on the concrete surface.
Guest suite in East Bend
4.97 out of 5 average rating, 118 reviews

Yadkin Wine Basic Betty

Guest suite/studio apartment attached to main home located in quiet and beautiful rural area in Yadkin Co. Includes full kitchen and full bath with all the necessities. TV with Roku and WIFI. Queen size bed and queen sofa bed. Two car parking and outdoor sitting space with fire pit. We're located in the middle of Yadkin Valley Wine Country so plenty of wineries to venture out to! We're also located 20 minutes from downtown Winston-Salem.

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, 106 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, 289 reviews

Charming quiet condo all to yourself

This is a cozy non pet condo for two. Perfect for 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 sign reading 'Welcome to the Joyful Loft' is displayed prominently, crafted from wood with a black graphic design. The sign is hung on a textured wooden surface, with steps visible in the background leading to the entrance.
Apartment in Winston-Salem
4.96 out of 5 average rating, 104 reviews

Joyful Loft! Private Stylish Apartment!

This unique place has a style all its own. This is a stylish studio apartment with a full bathroom and small kitchenette. The space is completely separate from the main house and is located above the garage with a separate entrance to the right of the garage. You will need to go up the stairs to the right of the garage to access the apartment.

Popular amenities for Winston-Salem vacation rentals

When is the best time to visit Winston-Salem?

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Frequently Asked Questions

  • Where should I stay in Winston-Salem?

    Make yourself at home in Winston-Salem by choosing from our most frequently booked neighborhoods. We have over 440 vacation rentals in West Salem, and over 440 vacation rentals in Ardmore.

  • Are there vacation rentals with a dedicated workspace in Winston-Salem?

    Yes! Work meets play with ease at over 620 vacation rentals in Winston-Salem featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Four-legged friends are welcome in Winston-Salem. Choose from more than 390 vacation rentals for guests traveling with pets.

  • Are there Winston-Salem vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 70 vacation homes with pools in Winston-Salem, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in guesthouse rentals in Winston-Salem?

    Experience the best of Winston-Salem with our guesthouse rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for Apartment Rentals in Winston-Salem?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with self check-in, over 20 homes with a gym, over 170 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Winston-Salem have a bbq area?

    Absolutely! We offer over 60 house rentals with a bbq area in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Winston-Salem have self check-in?

    Absolutely! We offer over 10 condo rentals with self check-in in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Winston-Salem have a gym?

    Absolutely! We offer over 20 apartment rentals with a gym in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.

  • Do boutique hotel rentals in Winston-Salem have wifi?

    Absolutely! We offer over 10 boutique hotel rentals with wifi in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.

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 € 17 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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