House holiday rentals 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

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

Cozy King Blue H2O Staycation , Pool & Hot Tub

Quiet secluded STAYCATION w/ Fully Fenced Back Yard for the PUPS. We have a hot tub for year round use and a Stock Tank Pool (Closed until 5/23/25) . A fire pit to unwind. Back yard BBQ with a built in bar top table and a cozy Sectional to enjoy the outdoors. Inside we have an amazing plush King size mattress to take all stress away. Full kitchen * Hot tub - I will do my best to have it available at all times unless there is a mechanical issue. (No refunds if hot tub is not available)

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!

Awakening Path

Welcome to a serene retreat nestled among a wooded forest, a gurgling brook, a candlelit fairy house and trail, the cutest and most loving pony ever and his equine friend, Ginger, a gentle chestnut mare. The charming cottage features warm wood floors, two inviting bedrooms downstairs, along with a spacious living area and a well-equipped kitchen. An additional bedroom upstairs offers extra comfort and privacy, accommodating at least two guests, and a beautiful view of the outdoor splendor.

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

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.

Tiny tiny house from 1930 near Wake

102 year old eclectic tiny house, 375 sqft Fun, bright and lively. Pets must be pre approved. Within 2 miles of Wake Forest, half mile from US- 52 and 20 m High Point. Less than 7 minutes to downtown WS! Convenient to everything, including Pilot Mountain and Hanging Rock State Park. No Vaping or Smoking. Private setting. Can be rented with house next door. *Pets must be pre approved before booking . *follow directions from website. No 3rd party bookings! I check ID

Duke's Place - Tranquil Farmhouse Retreat

Modern farmhouse situated on a spacious lot, offering a perfect balance of privacy and convenience. Located just outside Lexington and Winston-Salem, this property is also a short drive from Greensboro, High Point, and Salisbury, and just about an hour from Charlotte. Fully furnished, spacious fenced-in backyard, large parking area, covered front & back porches—perfect for relaxing, and conveniently close to major cities while enjoying the peace of rural living.