House holiday rentals in Winston-Salem

Old Salem Restored Moravian Village 1700s

Historical Home in the heart of Old Salem. House includes use of Two Bedrooms and two separate bathrooms, living room, dining room , kitchen and private back porch and patio. Additional small room with single bed. The house is private. Close to Muddy Creek Café, Meridian Restaurant, and Di Lisio's, Italian Restaurant. Private second living area with separate entrance for host below the living quarters. Events, filming and photography require approval. Close to downtown and Salem Lake.

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

Vintage Modern Synthesis in the Heart of W-S

Refurbished 1910 bungalow in West Salem Historic District within walking distance to downtown, Old Salem, baseball stadium, breweries, and more. Private 2BR/1BA home offers a unique vintage style with modern amenities. Open floorplan with high ceilings, exposed brick, and hard wood floors gives the feel of a loft apartment. The ambiance of the house lends itself to the historic industrial charm of old Winston. Professional Viking stove, clawfoot tub, custom bar space, private yard, parking.

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)

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.

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.

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.

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.

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.