Holiday rentals 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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Top guest favourite
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, 213 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

Guest favourite
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 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
4.99 out of 5 average rating, 307 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 favourite
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.
Flat in Downtown Winston-Salem
4.96 out of 5 average rating, 159 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 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, 178 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 favourite
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, 118 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 favourite
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.
Apartment in Winston-Salem
4.97 out of 5 average rating, 176 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 favourite
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.
Guest house in Germanton
4.96 out of 5 average rating, 515 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.

Guest favourite
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.
Flat in Winston-Salem
4.96 out of 5 average rating, 104 reviews

The Joyful Loft Apartment! Private Studio Retreat

Welcome to the Joyful Loft, a stylish and private studio retreat designed for comfort and convenience. Nestled above the garage with its own dedicated entrance, this cozy space offers complete privacy while still being close to everything Winston‑Salem has to offer. The separate entrance and private staircase, make the loft feel like your own personal hideaway. The Joyful Loft combines style, convenience, and a welcoming atmosphere.

Top guest favourite
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, 107 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 favourite
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.
Apartment in Ardmore
4.89 out of 5 average rating, 290 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 favourite
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, 110 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.

Popular amenities for Winston-Salem holiday rentals

When is the best time to visit Winston-Salem?

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Avg. price$131 SGD$129 SGD$129 SGD$144 SGD$145 SGD$138 SGD$137 SGD$136 SGD$141 SGD$146 SGD$138 SGD$133 SGD
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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 holiday rentals in Winston-Salem

  • Total holiday rentals

    Explore 1,000 holiday rentals in Winston-Salem

  • Nightly prices starting at

    Winston-Salem holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 46,400 verified reviews to help you choose

  • Family-friendly holiday rentals

    560 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 390 rentals that welcome pets

  • Holiday rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    620 properties have a dedicated workspace

  • Wifi availability

    980 of Winston-Salem holiday rentals include wifi 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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