House holiday rentals in Winston-Salem

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.

4.99 out of 5 average rating, 244 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

LocationFamilyCleanliness

5.0 out of 5 average rating, 107 reviews

Good View 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.

FamilyLocationWalkability

4.96 out of 5 average rating, 114 reviews

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.

ValueLocationLayout

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.

4.94 out of 5 average rating, 174 reviews

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

ValueFamilyCheckout

4.93 out of 5 average rating, 128 reviews

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

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

LocationFamilyAccuracy

A living area is presented with a cozy sectional couch facing a coffee table, paired with a small dining table. Light wood flooring is visible, and a staircase with dark steps leads to the upper level. A fire extinguisher is mounted for safety.

4.92 out of 5 average rating, 154 reviews

Camel City Hideaway

Welcome to your home away from home! Our stylish and centrally-located space is designed with comfort and convenience in mind. Whether you're in town for business or leisure, you'll love our prime location. Our cozy place features all the amenities you need to feel right at home, including a fully equipped kitchen, hotel-quality linens, a spacious living room, and a dedicated work area. We also provide toiletries in case you forgot. We aim to make your stay in Winston-Salem a memorable one!

FamilyValueComfort

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.

4.97 out of 5 average rating, 127 reviews

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!

FamilyValueNearby

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.

4.87 out of 5 average rating, 127 reviews

Downtown Charm, 3 Bdr, Near Rest and Bars

Explore Winston-Salem - our cozy 3-bedroom, 2-bath home, a short walk to bars, restaurants, and a famous brewery. Enjoy stylish comfort with TV-equipped bedrooms, a game area with foosball, and an outdoor fire pit. The fully equipped kitchen and dining area cater to your culinary needs. Located in downtown, it's your ideal base for city adventures. Amenities include WiFi, cable TV, essentials. Perfect for any visit, experience downtown charm and convenience in your home away from home

FamilyLocationGetting around

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.

4.98 out of 5 average rating, 129 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.

ValueFamilyQuiet

4.93 out of 5 average rating, 122 reviews

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.

FamilyLocationHeating

A single-family home features a light-colored exterior with blue shutters. A large, attached garage is visible, with a paved driveway leading to it. The front yard is well-maintained, showcasing shrubs and a tree with vibrant autumn foliage.

4.93 out of 5 average rating, 231 reviews

"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.

FamilyLocationParks

A modern kitchen is presented with white cabinetry and a spacious island featuring a wooden cutting board. Built-in appliances include a dishwasher and a stove. Natural light enters through large windows, while a small dining area with wooden chairs is visible in the adjacent room.