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Family-friendly vacation rentals in Winston-Salem

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Winston-Salem

  • Total vacation rentals

    Explore 560 vacation rentals in Winston-Salem

  • Nightly prices starting at

    Winston-Salem vacation rentals start at G$4,184 GYD per night before taxes and fees

  • Verified guest reviews

    Over 29,630 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 300 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    380 properties have a dedicated workspace

  • Wi-Fi availability

    560 of Winston-Salem vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winston-Salem rentals

  • 4.8 Average rating

    Winston-Salem stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Winston-Salem

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
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

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

FamilyIndoor spacesLocation

4.99 out of 5 average rating, 240 reviews
Top guest favorite
Home in Winston-Salem

Buena Vista Bungalow

In the most sought-after Buena Vista Neighborhood, this bungalow is all new, completely renovated, and beautifully decorated! This 1500+ sq ft gem has 3 bedrooms, 2 living spaces, 2 dining areas, a workstation, a furnished patio, and a private backyard. Only 0.8 miles from Grayln,  1.5 miles from Wake Forest, 2 miles from Downtown, and 3  miles from Old Salem. Walkable to bakeries (Bobby Boy's, The Remedy), shops, restaurants (The Porch, 1702), parks, and Joymonger Brewery! All within a mile.

Indoor spacesFamilyLayout

5.0 out of 5 average rating, 105 reviews
Top guest favorite
A spacious living area is showcased with a large blue sectional couch and a patterned ottoman. Natural light enters through a window next to the front door, while a decorative wall piece adds interest above the seating. A cozy area rug lies beneath the furniture.
Home in Ardmore

New in the Heart of Ardmore

The whole group will enjoy easy access to everything that Winston-Salem has to offer from this centrally located place. Our fully renovated home has everything brand new. Sleep on new tuft and needle mattresses, relax at the end of your day with our Frame TV, enjoy a full wrap around porch with BBQ, and enjoy our walkable neighborhood. From the popular Miller park, to the local staple eatery The Bagel Station, to the Original Krispy Kreme, we are walkable to dozens of Winson-Salems top visits.

KitchenIndoor spacesDecor

4.96 out of 5 average rating, 113 reviews
Top guest favorite
The charming exterior of a single-story home is presented, featuring a bright red front door. Flanking the entrance are two symmetrical windows, while landscaped bushes and a path lead to the porch. A tree provides shade, enhancing the welcoming appearance.
Home in Winston-Salem

The Walnut Cottage. Charming! Near Everything!

Relax in the historic West Salem district. Central to UNCSA, WSSU, WFU, Carolina University, hospitals, downtown, dining, shopping, parks/greenways and 18th century town of Old Salem. Enjoy cozy seating areas, or head out to the patio, relax on the screened porch or grill on the deck. Off street parking, WiFi, smart TVs in each room, updated kitchen with gas range. 2nd living room in mini suite with workspace and Ethernet port. Beds: 2 queens, 1 full and 1 futon. Keyless entry. Washer/Dryer

KitchenIndoor spacesCheck-in

4.94 out of 5 average rating, 172 reviews
Top guest favorite
The living area features a warm wooden interior with a stone fireplace at its center. A Chesterfield leather sofa and armchairs surround a rustic coffee table, positioned on an intricately patterned area rug. A spiral staircase leads to the upper level, with natural light streaming in from the adjacent deck.
Cabin in Winston-Salem

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.

FamilyIndoor spacesCheck-in

4.98 out of 5 average rating, 126 reviews
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

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.

Indoor spacesFamilyHiking

4.98 out of 5 average rating, 357 reviews
Top guest favorite
A charming 1920s era house is set against a backdrop of colorful autumn foliage. The house features a welcoming porch with stone accents, large front windows, and a well-maintained garden, creating an inviting exterior.
Home in Winston-Salem

Dragonfly: 1 Br Garden Apt Near WFU & Baptist Hosp

The "Dragonfly" is a spacious, peaceful 1BR garden terrace apartment (800 sq ft) in one of Winston-Salem’s most desirable neighborhoods. Just 1 mile from Baptist Hospital, 4 miles from Wake Forest University, and 10 minutes from downtown, this light-filled retreat is perfect for medical travelers, university visitors, couples, or small families. Features a king bed, washer/dryer, workspace with fast Wi-Fi, kitchenette, and private patio with garden views. Hi-chair & Packngo for families

Indoor spacesKitchenSleep quality

4.99 out of 5 average rating, 142 reviews
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 Winston-Salem

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.

FamilyKitchenHospitality

4.96 out of 5 average rating, 211 reviews
Guest favorite
A spacious loft bedroom features a king bed with neutral bedding and a cozy sitting area. Large windows provide natural light and views of the surrounding trees. The room is adorned with wooden walls and a combination of storage furniture.
Cabin in Lexington

Log Cabin with Hot Tub in N Lexington

Welcome to our beautiful 1880s log cabin, situated in a secluded location among the trees. Our cabin has been updated, and features a large porch as well as a hot tub. **Please note that while we do our best to keep the cabin free of pests they WILL get in due to the age of the cabin and how it was built. Usually it is stink bugs, lady bugs and mud daubers upstairs and tiny centipedes in the basement bedrooms. If you do not like the sight of bugs this is not the Airbnb for you!**

KitchenIndoor spacesComfort

4.93 out of 5 average rating, 137 reviews
Top guest favorite
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.
Guesthouse in Ardmore

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.

Indoor spacesKitchenHospitality

4.99 out of 5 average rating, 112 reviews
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.
Apartment in Ardmore

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.

KitchenFamilyOutdoor spaces

4.98 out of 5 average rating, 126 reviews
Top guest favorite
Cottage in Advance

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.

Indoor spacesFamilyAccess

5.0 out of 5 average rating, 258 reviews

Popular amenities for Winston-Salem family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Superhost
A private outdoor space features a round stock tank pool surrounded by a pebbled area. Two colorful inflatable pool toys rest in the water. Comfortable seating arrangements with woven chairs are paired with hammocks, creating a cozy atmosphere amidst lush greenery.
Home in Winston-Salem

Cozy King Blue H2O Staycation , Pool & Hot Tub

Indoor spacesFamilyCheckout

4.89 out of 5 average rating, 359 reviews
Top guest favorite
A serene outdoor space features a hot tub surrounded by wooden decking. A projected movie screen displays an ocean scene, illuminated by soft lights. The area presents a perfect setting for relaxation and entertainment at night.
Home in High Point

Hot Tub • Outdoor Movie • Near HPU – Pet Friendly

Indoor spacesFamilyValue

4.89 out of 5 average rating, 306 reviews
Top guest favorite
The exterior of a tiny house is illuminated at dusk, showcasing a combination of wooden and stone elements. A welcoming porch with two chairs is seen, and the surrounding trees create a serene backdrop, emphasizing the home’s integration with nature.
Treehouse in Boonville

“The Shack” on Farmer’s Creek

KitchenFamilyHospitality

5.0 out of 5 average rating, 121 reviews
Superhost
A wooden deck is shown in the image, featuring two lightweight chairs positioned beside a hot tub. A covered structure is visible nearby, providing a shaded area. Tall trees surround the space, contributing to a serene woodland setting.
Tiny home in Winston-Salem

Hot Tub Hideaway

FamilyKitchenComfort

4.89 out of 5 average rating, 115 reviews
Superhost
Home in High Point

Luxury 4BR High Point Retreat | Hot Tub | BBQ

KitchenIndoor spacesAccess

4.88 out of 5 average rating, 196 reviews
Top guest favorite
An open living area is illuminated by natural light, featuring a dining table with blue chairs and a modern kitchen with stainless steel appliances. A vibrant area rug adds color to the wooden floor. A ceiling fan enhances airflow in the spacious layout.
Home in Greensboro

Unsought discoveries await you! Serendipity

KitchenIndoor spacesLocation

4.98 out of 5 average rating, 117 reviews
Top guest favorite
A spacious living area features wooden beams and a stone fireplace, creating a warm environment. Large windows offer views of the lush outdoor landscape. Comfortable seating arrangements include a light-colored sofa, a patterned armchair, and a wooden coffee table, surrounded by natural light.
Home in Summerfield

Lovely Lodge on Horse Farm

FamilyKitchenBackyard

4.97 out of 5 average rating, 111 reviews
Top guest favorite
Home in Greensboro

Guilford Hills: Hot Tub / Fully Fenced / Pets

Indoor spacesFamilyCleanliness

4.97 out of 5 average rating, 115 reviews

Family- and pet-friendly home rentals

Top guest favorite
Home in Winston-Salem

Idlewilde Farmhouse | 4BR/3BA Walk to Wake Forest

FamilyIndoor spacesValue

4.93 out of 5 average rating, 118 reviews
Guest favorite
The main bedroom features a sizable bed with a dark gray throw and neatly arranged towels. Two bedside lamps provide soft illumination beside the bed. The room is complemented by two framed artworks, and a bathroom with glass door access is visible in the background.
Home in Winston-Salem

Beautiful 2 BR home with Office and Game Room

Indoor spacesFamilyBathroom

4.96 out of 5 average rating, 230 reviews
Top guest favorite
A living area features hardwood flooring and natural light from multiple windows. A comfortable sofa with decorative pillows faces a simple coffee table and a modern TV stand. A bright accent chair adds a pop of colour, creating a welcoming space.
Home in Winston-Salem

House in Washington Park, historic Winston-Salem

FamilyIndoor spacesBackyard

4.97 out of 5 average rating, 207 reviews
Guest favorite
A bright living room features a cozy seating arrangement with a light-colored sofa and two blue armchairs. A wooden coffee table rests on a soft area rug, while a wall clock adds a decorative touch. Natural light streams in through the window, enhancing the space.
Home in Winston-Salem

Modern Craftsman *Pet-Friendly* Near Downtown

KitchenIndoor spacesWifi

4.93 out of 5 average rating, 122 reviews
Guest favorite
The kitchen features grey cabinetry and stainless-steel appliances. A central island with a wooden top provides additional workspace. Natural light filters through a window above the sink, illuminating the organized countertop with a kettle and decorations.
Home in Winston-Salem

Modern & Tranquil | 5 min from WFU & Shopping

Indoor spacesKitchenGetting around

4.88 out of 5 average rating, 162 reviews
Top guest favorite
The spacious living area showcases wooden log walls and a warm atmosphere. A stone fireplace is centrally located, with a patterned area rug beneath a comfortable sofa. Large windows allow natural light to illuminate the room, while rustic decor complements the cabin's character.
Cabin in Winston-Salem

Majestic Getaway near Wake Forest University

KitchenIndoor spacesValue

4.96 out of 5 average rating, 233 reviews
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

Elegant Pet Friendly Ranch close to everything!

FamilyKitchenCleanliness

4.98 out of 5 average rating, 128 reviews
Superhost
The inviting exterior of a 1940's cape cod home is framed by lush greenery and blooming azaleas. The brick facade features white shutters and a welcoming front porch. A pathway leads to the entrance, creating a sense of approachability.
Home in Winston-Salem

*CHARMING* 3bd dogfriendly entire HOME close to DT

KitchenFamilyHospitality

4.87 out of 5 average rating, 271 reviews

Family-friendly home rentals with a pool

Top guest favorite
A cozy living space features a comfortable sofa with decorative pillows, complemented by a wall adorned with woven baskets. Soft sunlight filters through a nearby window, illuminating the area. A green plant adds a touch of nature, while a simple coffee table completes the setup.
Home in Winston-Salem

Cozy Townhouse close to WFU!

Indoor spacesFamilyPool

4.94 out of 5 average rating, 125 reviews
Top guest favorite
A serene view of a green landscape is provided from a covered porch. Two rocking chairs face an open yard with a small table, leading toward a rustic building in the background. A prominent mountain peak is visible in the distance under a partly cloudy sky.
Farm stay in Pinnacle

Beautiful Retreat at Pilot Mountain Vineyards

FamilyIndoor spacesGetting around

4.91 out of 5 average rating, 295 reviews
Guest favorite
A spacious living room features two velvet sofas in soft pink hues, arranged around a coffee table. A built-in fireplace sits against a light-colored wall, while natural light filters through the blinds, creating a warm atmosphere. A dining area is visible in the background.
Home in Greensboro

Townhouse near the Airport

KitchenFamilyTV

4.85 out of 5 average rating, 118 reviews
Top guest favorite
A two-story home is situated in a serene setting, surrounded by trees displaying autumn colors. Features include a driveway leading to a two-car garage and a spacious front porch with railings. Large windows allow natural light to brighten the interior.
Cabin in Pinnacle

"LOG OUT" in our Private 3 Bedroom Cabin

Indoor spacesFamilyBreakfast

4.98 out of 5 average rating, 121 reviews
Guest favorite
The exterior view of The Cave showcases a home illuminated at dusk, featuring a well-lit pool area. A welcoming sign states 'The Cave: An Oasis for Adults.' The indoor lounge area displays a cozy setup with modern lighting and a large screen welcoming guests.
Guest suite in Greensboro

Peaceful Adult Oasis • Pvt Pool, Theatres, More

KitchenIndoor spacesAccuracy

4.93 out of 5 average rating, 152 reviews
Guest favorite
A modern kitchen features sleek black cabinetry and stainless steel appliances. An elegant round dining table occupies the center, surrounded by transparent chairs. Blue accent walls complement the minimalist design, while soft lighting from pendant fixtures enhances the ambiance.
Condo in High Point

Modern/Retro Luxury Condo

FamilyKitchenComfort

4.97 out of 5 average rating, 202 reviews
Guest favorite
A spacious living area features a dark sectional sofa complemented by a patterned ottoman. A small blue stool provides additional seating. Shelves are mounted on the walls, holding decorative items. Light permeates through window treatments, enhancing the overall brightness of the room.
Townhouse in Winston-Salem

Cozy & Convenient

Indoor spacesFamilyLayout

4.92 out of 5 average rating, 12 reviews
Top guest favorite
Home in Ardmore

Light and Bright Condo w/POOL - WFU, Atrium Hosp

KitchenIndoor spacesPool

4.96 out of 5 average rating, 25 reviews

Destinations to explore