Family-friendly holiday rentals in Winston-Salem

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

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

Black Bear Cabin - 3BR/2BA - Fire Pit, Arcade

This picturesque log cabin home offers a mountain-like escape, just a short drive from the city where towering pines and abundant fresh air surround you. With vaulted ceilings, a stone fireplace and beautiful exposed beams, the home radiates charm. Settle in for a night around the firepit, play the arcade & pool table or cozy up by the fire with a good book. You’ll be only 4 mins from a supermarket and only 20 minutes from the heart of the city giving you the ultimate city break getaway.

House in Washington Park, historic Winston-Salem

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!

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.

Beautiful 2 BR home with Office and Game Room

This beautifully decorated 2 bedroom home, part of a duplex, comes with high-speed Internet and Wi-Fi. It includes an office and a game room. It is near shopping, hospitals, and the rest of the Winston-Salem scene. The kitchen has all the tools needed to prepare your favorite meals. The TV in the living room includes Disney+. Everything except the game room is on the main level. The back deck is ready for hosting a barbecue, with a view of the backyard and adjoining green space.

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.

🌹Rose Room Apartment, West Salem Art Hotel

Welcome to the West Salem Art Hotel! This eclectic and beautiful apartment is in a 1931 historic brick building, a stone's throw from Downtown Winston-Salem and a 3-minute walk to Truist Ballpark! It is so close to downtown without all the city noise, and it is located in the middle of a peaceful urban garden! Free Parking! A short walk away from W-S's best eateries/entertainment! Private, unique, and Clean!

Rocky Knoll Hideaway | Visit Family | Quiet Escape

Welcome to Rocky Knoll Hideaway — your peaceful home base for visiting family, relaxing, and recharging. Tucked among the trees, this cozy private cottage offers the perfect blend of quiet seclusion and convenient access to the area. Whether you’re here for a weekend visit, a holiday stay, or just a break from the busy pace of life, Rocky Knoll Hideaway offers a warm, welcoming place to land.

"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.

Historic home in Grace Park

From your first steps onto this property, you know you are looking at something special. Before you even enter the house, there will be no question that staying in a historic home of this stature is a rarity. This residence has been carefully renovated to retain the original charm of 1920 and preserve history, while including modern updates and conveniences.

The Blue Door Cabin

This tiny cabin is brand new and nestled just inside the woods, but only 1/2 mile from I-74 and only 10 min. to downtown Winston Salem, NC. This little cabin was built just for Airbnb guests, it has granite tops, stained concrete floors, a beautiful tiled/stone shower, and will surely help you unwind and enjoy your stay in this delightful space!