House holiday rentals in Winston-Salem

Wake Forest University Home

Your home away from home! This 3 bed/2 bath home is located between Wake Forest University and WS Downtown. Minutes away from Truist Field and LJVM Coliseum. Walking distance to Wake. 6-10$ UBER ride distance from downtown restaurants and pubs. Stay close to everywhere, offers free WiFi, washer/dryer upon a 3 day stay, and great community/work bar to share w/family and friends. Work visit? College tour? Visiting your kid at Wake or family in Winston? We would love to host you! Come on by!

Luxurious, Historic 4BR Home in Downtown Winston

If you’re looking for a home with comfort and charm, this is the place for you! It has been renovated with the historic nature of the property in mind. There is an amazing amount of space for a big family or group of friends, with 4 bedrooms and 3 bathrooms. Luxurious furnishings and antique touches make you feel like you’re staying in an upscale hotel without the price- and with your own privacy. One of the best parts of this home is the location- walking-distance from downtown 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

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.

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!

House in Washington Park, w/NC beer tasting

I love my neighborhood! Brand New Location for me! Relax with the family at this peaceful place to stay! If you are just passing through or traveling for work, this is the perfect place for you! Located in Washington Park (which is just 2 miles from Downtown), you will have easy access to all Winston has to offer! I also own Hoots Beer Company, and I will be happy to give you a beer tasting! If you see a concert you want to attend at my place, a free ticket is on me! Side note: NO PARTIES!

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 check in 3pm-10pm

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

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.

Deacon Stays: The Polo - Walk to WFU

Completely renovated in 2023! Our charming home is just a short walk or drive away from the city’s best offerings as well as being located just minutes away from Wake Forest University’s campus. Walk through the front door of this little brick house and feel right at ease in a quiet residential neighborhood with easy access to a lively campus and thriving downtown. Our home is perfect for larger groups! Find out together why Winston Salem is a top choice for an easy weekend getaway.