Condo holiday rentals in Winston-Salem

The lovely 2 bedroom Greensboro Hideaway

Keep it simple at this peaceful and conveniently located Greensboro hideaway. A short drive from the area colleges, attractions and entertainment venues, the hideaway provides a quiet place to relax when your travels bring you to the Greensboro area. Central location allows easy rideshare travel from PTI airport If work brings you to town, wifi and an ethernet cable allows easy connections for quality video calls along with Chromecast. Board Games & Air filtration system!!! *NO PARTIES*

2 bedroom condo in High Point-Uptown/Downtown

Historic condo in the heart of High Point, 2nd floor stair access. Children 12 and over welcome. Walk to High Point Univ., HPFM, Baseball Stadium, Children’s Museum, Restaurants, Breweries, JH Adams Inn, Greenway, Pickleball Courts, Library, Farmers Market and more. Stroll along historic tree lined, shady streets. Oak Hollow Lake is just 5 minutes away or City Lake Park in Jamestown. Winston Salem and Greensboro are just 20 minutes away. 20 minute drive to the airport. Walk to Amtrak Station.

2 Bed,1 Bath w/King: Downtown, Near Tanger/A&T/GAC

Welcome to downtown Greensboro, NC! From your Airbnb in the Dunleath Historic Neighborhood, you’ll be just moments from the Tanger Performing Arts Center for a live show, First National Bank Field to cheer on the Grasshoppers baseball team, just a few yards from the Downtown Greenway. Enjoy delicious meals at nearby restaurants, explore LeBauer Park, enjoy unique local shops and the farmers market, and soak in Greensboro’s vibrant charm. Your adventure starts here—please make yourself at home!

Downtown Oasis Central to Everything Winston

Experience Winston-Salem like a local in this fully updated & beautifully decorated 1-bedroom+ condo. Nestled in the heart of the city, you're steps away from theaters, restaurants, breweries, & the convention center, yet a quick drive to WFU, WSSU & The Joel. The 900+ sq. ft unit offers an inviting bedroom w/ queen, 1.5 bathrooms, flex room w/ oversized single futon chair, living room w/queen sleeper sofa, dining room and kitchen complete w/ Keurig & pods, pots & pans and some spices too.

Walk to CarolinaTheater/PRYLE/Coffee/Restaurants!

Stay in a former 1920s grocery storefront—now a stylish, boutique condo with 11-ft ceilings and massive front windows draped in velvet for total privacy. Zero steps to enter! Enjoy a cozy open layout, Roku TV, fast Wi-Fi, and a private bedroom with blackout drapes and a luxe hybrid queen bed. Kitchen is fully equipped, and bathroom includes plush towels, premium toiletries, and a hair dryer. Unique, walkable, and full of charm—this space is truly one of a kind! Pet friendly w/fee (no carpets)

Designer Loft in the heart of the Triad

The Kerners Loft is a stylish boutique Airbnb tucked inside a restored factory in the heart of downtown Kernersville, NC. With high ceilings, exposed brick, and a design- forward aesthetic, this space blends together it's industrial roots with curated comfort. Whether your travels bring you in for work, or pleasure, The Kerners Loft is your stylish home base for your getaway! Centrally located in the Triad, we are minutes away from PTI airport, Greensboro, Winston-Salem, and High Point.

King Bed-Huge Windows-Heart of Downtown Greensboro

Adorable condo is close to everything! Walk to shopping, museums, restaurants, coffee shops, bars, Tanger Center, grocery, city parks, and more. Also walking distance to UNC Greensboro, NC A&T, and Elon Law. 65" Smart TV in living room. All amenities including washer, dryer, dishwasher and microwave. Coffees, teas, filtered water and snacks provided. All bedding, towels and linens. Whether you like nightlife, walks in the park, or trying new restaurants, Downtown Greensboro has it all!

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.

1 Bedroom Downtown near Tanger, Stadium, UNCG

The Blessing House-GSO built in the 1940's is located on a quiet non-thru street in the Bellemeade District of Gboro and on the cusp of the Westerwood neighborhood. It is conveniently located and walkable to many areas, ie. hospitals-(5 minutes or 2 miles), downtown, ball park, shopping center, grocery store, Coliseum, Tanger Performing Arts Center, International Civil Rights Museum, NCAT, UNCG, Greensboro College, Guilford College, and the High Point Market is about 25 minutes away.

Old Salem Getaway - Visit DTWS via the Strollway

We love our comfy third floor condo with elevator access. Whether you are in town for business or pleasure, this condo fits the bill. Walk to Old Salem, UNCSA, and Salem College. Jog or bike Salem Creek trail, which is at our doorstep. Stroll through Old Salem on your way to downtown’s amazing eateries and breweries. Close by are Wake Forest University, WSSU and downtown Winston-Salem, and hospitals - this condo is central to anywhere in the Winston-Salem area.

Cozy Apartment in Peaceful Archdale

Enjoy a warm cozy stay at this 2 bed 1 bath apartment. Available is a 55 inch TV with Netflix available on the comfort of new couches. All the bed are equipped with 10 inch memory foam mattress that make for the absolute best night sleep. High speed google wifi along with a work station makes all your work from home needs a breeze. Fully stocked kitchen for all your cooking needs. Entire coffee station to create the ultimate brew. I hope my place treats you well!

West End Charm

Welcome to Shenandoah Condominiums! Nestled in Winston-Salem’s historic West End, this bright one-bedroom condo blends vintage charm with modern comfort. Enjoy hardwood floors, natural light, a full kitchen, and a private screened porch—perfect for morning coffee or relaxing evenings. Easy walk to downtown restaurants, shops, bars, breweries, and the Benton Convention Center. The ideal home base for work or a weekend getaway!