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Family-friendly vacation rentals in Winston-Salem

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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

4.99 out of 5 average rating, 244 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.

5.0 out of 5 average rating, 107 reviews
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.

4.96 out of 5 average rating, 114 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

4.94 out of 5 average rating, 174 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.

4.98 out of 5 average rating, 363 reviews
Guest favorite
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

Grey Sapphire Hideaway - 2BR/2BA, Game Room & Pool

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!

4.97 out of 5 average rating, 127 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

4.99 out of 5 average rating, 144 reviews
Guest favorite
A two-story brick home is framed by manicured greenery and stone steps leading to the entrance. A spacious front porch, bordered by white railings, provides a welcoming area to enjoy the outdoors. The home features large windows that allow natural light to illuminate the façade.
Home in Winston-Salem

Historic Beauty: 5BR Home with Yard Near Hospital

This is a beautiful home, lovingly renovated to retain the original 1920s charm and preserve history, while including modern updates and conveniences. It is perfectly located in the heart of Winston Salem- only a few blocks from Wake Forest Baptist Hospital and less than a mile from downtown. Despite the city location, it features a 3 car garage and over 0.3 acres of lot space in the form of a great backyard. Additionally, it sits across the street from beautiful Hanes Park.

4.91 out of 5 average rating, 324 reviews
Top guest favorite
Home in Winston-Salem

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

A modern farmhouse for groups visiting Wake Forest University and The Grounds — 4 bedrooms, 3 full baths, sleeps 10. 106 reviews at 4.93★. Stone fireplace, chef's kitchen, two private bedroom suites, hardwood floors. Walking distance to Allegacy Stadium, Couch Ballpark, LJVM Coliseum, and the new Grounds retail village. Need more space? We also offer this home combined with the back cottage for up to 16 guests with the whole property to yourselves. Pet-friendly. Superhost.

4.93 out of 5 average rating, 122 reviews
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

Entire COZY Unit - 3 min walk to WFU.

Welcome to your cozy - little nest. 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: - 5 min walk to WFU Campus. - 5 min drive to Downtown. - 3 min drive to Stadiums and Restaurants. - 10min drive to Wake Forest Baptist Hospital. - Reynolda House museum.

4.96 out of 5 average rating, 240 reviews
Top guest favorite
A spacious outdoor area is surrounded by colorful autumn foliage, featuring two distinct buildings. One structure is a single-story unit with a covered entrance, while the other is a two-story building with large windows. A sign in the foreground indicates that pets are welcome and there are no cleaning fees.
Guesthouse in Clemmons

Bee Happy- Studio & Pets Welcome- No cleaning Fees

Welcome to the "Bee Happy" a self-check in retreat for anyone needing a clean, peaceful retreat to rest a weary head, visit locally or just get away from it all. Pets are always welcome and are as pampered as our guests (Please read our important Pet Policy below). Our large, private outdoor deck is complete with a small side yard and fenced for your pet's safety. Our neighborhood is beautiful, secluded and in a perfect location that is close to I-40, Parks, restaurants.

4.96 out of 5 average rating, 316 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.

4.99 out of 5 average rating, 118 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

4.88 out of 5 average rating, 362 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

4.89 out of 5 average rating, 308 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

4.89 out of 5 average rating, 116 reviews
Superhost
Home in High Point

Luxury 4BR High Point Retreat | Hot Tub | BBQ

4.88 out of 5 average rating, 199 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

5.0 out of 5 average rating, 121 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

4.97 out of 5 average rating, 112 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

4.98 out of 5 average rating, 120 reviews
Top guest favorite
An outdoor seating area features comfortable wicker furniture arranged around a central fire pit. A spacious hot tub is positioned beneath a wooden pergola. Nearby, a charcoal grill is ready for use, all surrounded by a serene natural setting with trees and leaves.
Home in Greensboro

Hot Tub Hideaway, Cozy Home, Private Workspace

4.95 out of 5 average rating, 121 reviews

Family- and pet-friendly home rentals

Guest favorite
The bedroom features a spacious bed dressed with soft linens, flanked by two nightstands with lamps. Large windows are adorned with light curtains, allowing natural light. A cozy area rug lies beneath a vintage bench, while an antique mirror adds character to the room.
Apartment in Winston-Salem

Light & Bright West Salem 2nd Floor Apartment

4.88 out of 5 average rating, 113 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

4.87 out of 5 average rating, 272 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

4.93 out of 5 average rating, 124 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

4.87 out of 5 average rating, 170 reviews
Guest favorite
An open living area is shown, featuring a foosball table in the foreground. A cozy seating arrangement is visible, complemented by a stone accent wall and large windows. Light-colored walls and warm wooden flooring enhance the inviting atmosphere of the space.
Home in Winston-Salem

Downtown Charm, 3 Bdr, Near Rest and Bars

4.87 out of 5 average rating, 127 reviews
Top guest favorite
A cozy living area features a pink sofa with decorative cushions, positioned near a rustic coffee table. A television is mounted on the wall, while large windows allow natural light to fill the space. Soft lighting is provided by two lamps, enhancing the comfortable ambiance.
Cottage in Lewisville

Secluded cottage on 8 acres right outside of WS

4.94 out of 5 average rating, 136 reviews
Top 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

Mel’s country cottage. Country life near the city.

4.96 out of 5 average rating, 571 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

4.96 out of 5 average rating, 234 reviews

Family-friendly home rentals with a pool

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!

4.95 out of 5 average rating, 128 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

4.98 out of 5 average rating, 122 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

4.85 out of 5 average rating, 121 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

4.91 out of 5 average rating, 299 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

The Cave • Adult Oasis • Pvt Pool Open until 9/20

4.94 out of 5 average rating, 154 reviews
Superhost
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

4.97 out of 5 average rating, 202 reviews
Guest favorite
Home in Ardmore

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

4.92 out of 5 average rating, 26 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

4.92 out of 5 average rating, 12 reviews

Destinations to explore