Holiday rentals in Winston-Salem

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Quick stats about holiday rentals in Winston-Salem

  • Total holiday rentals

    Explore 1,010 holiday rentals in Winston-Salem

  • Nightly prices starting at

    Winston-Salem holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 48,320 verified reviews to help you choose

  • Family-friendly holiday rentals

    560 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 400 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    690 properties have a dedicated workspace

  • Wifi availability

    1,000 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!

Top-rated holiday rentals in Winston-Salem

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

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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
4.99 out of 5 average rating, 231 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

Superhost
A spacious bedroom features a large bed with a tufted headboard and an elegant navy bedspread. A pair of nightstands flank the bed, and a large mirror reflects the soft light. Neutral-toned walls and modern shelving enhance the inviting atmosphere.
Guest suite in Winston-Salem
4.96 out of 5 average rating, 162 reviews

West End Jewel - Large 1 Bed/1 Bath Near Everything!

Newly renovated 1 bed, 1 bath unit in the historic West End neighborhood of Winston Salem. Conveniently located near 2 hospitals, Hanes Park, the YMCA, the ballpark, and downtown; this place has it all! In addition to historic character and a wraparound porch, you will fall in love with the spacious shower with rainfall and standard shower heads, and sleep well in the large bedroom featuring a pillow top, king size bed and black-out curtains over the bedroom windows. Washer and dryer is included

Guest favourite
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
4.93 out of 5 average rating, 123 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 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
4.98 out of 5 average rating, 345 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
Home in Winston-Salem
4.97 out of 5 average rating, 197 reviews

Salem Twin Deck

Conveniently located in downtown Winston-Salem, this well-maintained cottage built in 1900 includes a recently updated kitchen with island, wood floors, dining room, living room with full futon, washer/dryer, bedroom with queen, beautiful bathroom and walk-in shower. Easy walking distance to downtown restaurants, short drive to WFU main campus, Med School, WSSU and UNCSA. One off-street parking spot available. Self check-in only, but we live next door if you need anything or have questions.

Top guest favourite
An open living and kitchen area is highlighted by a modern design and rich hardwood floors. A comfortable sofa and stylish chairs are arranged around a wooden coffee table. A bar seating area features stools near the kitchen, where sleek appliances and overhead lighting are visible.
Flat in Ardmore
4.91 out of 5 average rating, 104 reviews

Stylish 1BR Apt w/KING Bed in Central Location

Come stay in this newly renovated, beautiful apartment located just 1,500 feet from Baptist Hospital and 1 mile from downtown. Seasoned hosts will ensure that every amenity you need and desire is provided. This sparkling, clean apartment allows for the chance to get away while still providing the comforts of home. A first floor apartment, it has a large, open kitchen with brand new appliances and all the utensils, pots/pans, small appliances - and even spices- you need to make any meal!

Top guest favourite
A modern living area features plush gray sofas positioned around a glass coffee table. Large sliding doors provide access to a wooden deck. A wall-mounted TV and electric fireplace enhance the contemporary design, while vibrant yellow drapes add a pop of color.
Home in Winston-Salem
4.97 out of 5 average rating, 109 reviews

Grey Sapphire Hideaway - 2BR/2BA w/ Arcade

Nestled along a leafy tree-lined street in a quiet neighborhood is this stylish property with all the modern comforts of home and an inviting community pool waiting for you to enjoy. Inside this modern hideaway, you’ll find plush sofas, a warm fireplace, a gourmet kitchen, king and queen bedrooms and a bright sunroom filled with a Pac-Man arcade & an air hockey table. Centrally located only minutes from Hanes Mall, Downtown Winston Salem, Medical Centers, shops, restaurants, and more!

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 Winston-Salem
4.96 out of 5 average rating, 208 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 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, 127 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 living space features a small round table accompanied by two chairs and a kitchenette in the corner. A spacious bed is visible, with soft bedding draping over it. Natural light enters through the windows, and a full-length mirror is mounted on the wall.
Guest house in Ardmore
4.99 out of 5 average rating, 101 reviews

Rosewood Carriage House

Enjoy a relaxing stay at this peaceful and centrally-located space. Cannot beat location! Only a 1/2 mile from Atrium WFU Baptist Medical Center, 3 miles to WFU and Reynolda Village, minutes from downtown and Forsyth Medical Center. Walkable to Thruway shopping center restaurants and shops. Fully equipped kitchenette, brand new bathroom, and king size bed with luxury bedding. The private back patio feels cozy and secluded even in the middle of a bustling neighborhood.

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.
Flat in Ardmore
4.98 out of 5 average rating, 120 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 is presented, featuring a spacious bed adorned with a rust-colored quilt. A decorative lamp casts light beside a dark wood nightstand, accentuated by sculptural art pieces on display. A soft texture of a woven rug completes the inviting atmosphere.
Flat in Winston-Salem
4.95 out of 5 average rating, 325 reviews

West Salem Art Hotel, "Art"partment #1

Welcome to the West Salem Art Hotel! This eclectic and beautiful apartment is located in a 1931 historic brick building only 1 mile from Downtown Winston-Salem! All the conveniences of staying JUST on the outskirts in Historic West Salem, without all the city noise, AND located in the middle of a peaceful urban garden! We are minutes away from the best eateries/entertainment W-S offers! Private, unique, and clean.

Popular amenities for Winston-Salem holiday rentals

When is the best time to visit Winston-Salem?

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Avg. price£79£78£79£84£85£81£80£79£82£89£85£82
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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.

Destinations to explore