Family-friendly holiday rentals in Winston-Salem

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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 favourite

Home in Winston-Salem

4.84 out of 5 average rating, 165 reviews

Cozy Ardmore Cottage Main Level

Main level unit of a two apartment house located just minutes from downtown Winston-Salem, Baptist Hospital, & BB&T Field in the charming Ardmore neighborhood. Easy access to both 40 & 421. Built in 1945, and updated to provide comfort, security, & character, the open floor-plan is perfect for relaxing & connecting. Whether you are staying for one night or a month, this house will make you feel right at home. The light, colorful decor & natural light encourages good times & great possibilities.

9–16 Dec

£137 per night

Guest favourite

Guest house in Greensboro

4.97 out of 5 average rating, 1105 reviews

A charmer!Great spot near downtown.

A sunny garden studio in peaceful Fisher Park historic neighborhood that's an easy walk to downtown, restaurants/breweries, baseball stadium. Perfect location. Private with a separate entrance. One queen bed and a love seat pull out bed that sleeps one (in separate room). Wifi. Plenty of on street parking. The kitchenette area has a microwave, coffee pot (I provide coffee/tea & bottled water), mini fridge w/ sm freezer. Private outdoor garden area with table, chairs & umbrella. Keyless entry.

16–23 Dec

£78 per night

Guest favourite

Home in Winston-Salem

4.99 out of 5 average rating, 159 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.

7–14 Aug

£130 per night

Guest favourite

Guest suite in Winston-Salem

4.99 out of 5 average rating, 509 reviews

The Man Cave

The Man Cave is close to the highway. It is minutes away from downtown Winston-Salem, Wake Forest University, Hanes Mall, and Baptist Hospital. You'll love the place because of its private entrance and great "Man Cave" amenities... King bed, wi-fi, pool table, dartboard, 50" TV & DirecTV satellite cable, Keurig machine, full kitchen, washer/dryer, etc. Don't let the name fool you... It is good for a couples get away, solo adventurers, and business travelers looking for a unique experience.

1–8 Sept

£141 per night

Guest favourite

Home in Winston-Salem

5.0 out of 5 average rating, 257 reviews

Adorable, Stylish near UNCSA and Downtown

Walk to beautiful Old Salem and Cobblestone farmers market, coffee shops, brewery and restaurants. Minutes from UNCSA and Downtown, this adorable, private 2Bed/2Bath Arts & Crafts home has been completely remodeled with stylish interior space, huge kitchen, lovely living room, and gorgeous rainfall showers. Strict Covid-19 cleaning and disinfecting protocol followed. Lockbox allows for flexible, no contact, check in. One small dog, under 20lbs allowed with prior approval and fee, see rules.

12–19 Jul

£208 per night

Guest favourite

Tiny home in Thomasville

4.96 out of 5 average rating, 181 reviews

The Shack at Abiding Place - So Cozy and Peaceful

This cozy one bedroom cabin is the perfect get-a-way for singles or couples. Whether you want to enjoy the peace and quiet of a country setting, visit the farm animals on the property, or hang out by the fire-pit and roast marshmallows, you certainly will feel refreshed as you spend time here. This cabin is located on the Abiding Place property, a place for retreat, renewal, and restoration. Conveniently located close to High Point (Furniture Market), and other Towns/Cities of theTriad, NC.

2–9 Apr

£73 per night

Guest favourite

Apartment in Winston-Salem

4.9 out of 5 average rating, 381 reviews

Sanctuary – 1bedroom & 1bathroom

My modern and convenient condo located in the heart of Winston-Salem’s shopping district will provide you with a 1 bedroom & bathroom space. The condo is professionally furnished and cleaned to provide a 5 star experience. Basic appliances provided (microwave, kitchen appliances, washer & dryer, dishwasher, Keurig). Very spacious with patio furniture for extra relaxation! You can also enjoy the community pool and gym. This space is NOT shared. Guests have the entire space to themselves.

21–28 Jun

£115 per night

Guest favourite

Home in Winston-Salem

4.97 out of 5 average rating, 131 reviews

Cozy 3 Bedroom Home with Fenced Back Yard

A cozy 3 bedroom family home with a living room, den, two bathrooms, and screened porch. Home was fully renovated in 2017. Bathrooms feature dual granite topped vanities, new tubs and ceramic tile. There is new laminate flooring throughout the home, new kitchen cabinets and ceiling fans in the bedrooms. Fully fenced back yard. Centrally located with fast access to Wake Forest, Salem College, Winston-Salem State, Wake Forest Baptist Hospital and Forsyth Hospital. Home is pet friendly.

19–26 Feb

£160 per night

Guest favourite

Home in Dobson

4.97 out of 5 average rating, 424 reviews

Stony Knoll Vineyards Wine Lodge

A family heritage 1850 log home that was completely renovated in 2007. The front porch overlooks Stony Knoll vineyard grounds and tasting room which is across the street. This wine lodge consists of 1 full bath with a shower and jacuzzi, 1 double bed, 1 king bed and 1 single bed loft. A fully furnished kitchen for all meal prep. A full sized living room with fireplace and TV. Come and enjoy a glass of wine on the front porch or listen to the rain hit the country tin roof.

20–27 Oct

£142 per night

Guest favourite

Home in High Point

4.94 out of 5 average rating, 385 reviews

Bright and Open Renovated Home.

Fully remodeled home with modern & rustic accents throughout! 3 bedrooms available, featuring LED Smart TVs, king, and queen beds. Master has an on-suite master bathroom and closet. Living room has a 65" LED smart tv, sectional , and leather club chair. Private 6’ fenced in back yard with walkout deck, outdoor couch & teak patio table.This home is excellent for couples, business travelers, and families looking for a home away from home experience.

4–11 Feb

£147 per night

Guest favourite

Flat in Winston-Salem

4.88 out of 5 average rating, 411 reviews

Summit Street Garden Apartment

450 square foot garden/lower level private studio apartment located on quiet street in historic district. Easy walking distance to Benton Convention Center, downtown restaurants and entertainment. Within 10 minutes of WFU, WSSU and Salem College. Keyless, private entrance, coffee and area entertainment recommendations provided. Pet friendly. Great space for families. Limited space and privacy for 4 adults.

5–12 Jun

£99 per night

Guest favourite

Cabin in Winston-Salem

4.97 out of 5 average rating, 177 reviews

Majestic Getaway near Wake Forest University

Our unique Cabin is a 3 bd, 3 ba with en suite/family room and comfy sofa bed for a fourth bedroom option. Wifi, TV (Roku, At&t TV NOW, Netflix, Amazon, Hulu etc available for you to sign into if you have an account. We provide Netflix ), fully equipped kitchen, laundry, large porches, great coal grill and wonderful secludedness. Lovely for a small family get together to a magical stay-cation!

7–14 Mar

£284 per night