A hand-picked list of downtown Winston-Salem’s most unique Airbnb stays
Travel Guide | March 2024
We scoured Airbnb for the most unique, top-rated short-term rentals in downtown Winston-Salem. This list is for those looking to immerse themselves in Winston’s artistic culture and historical heritage.
P.S. We saved the best for last, with #10 being our favorite!
Salem Twin Deck
Tucked away down a private garden walkway and behind a gated fence, you’ll be amazed at the magical world hidden in the trees and flowers of downtown Winston-Salem. Salem Twin Deck is a quiet and private short-term rental in downtown Winston. The overall consensus is that the online photos of this 1900 cottage don’t do it justice.
4.99 stars / 155 Reviews
Airbnb “guest favorite”
Superhost
Why you’ll love it:
- A hidden, private garden oasis in the city.
- Within walking distance of restaurants, coffee shops, and bars.
- The rooftop deck is perfect for relaxing and watching fireworks.
- It’s better in person than in the photos
K-Obscura, Krankie’s Coffee
Upstairs from Krankie’s Coffee is a historic loft in downtown Winston-Salem, perfect for a weekend stay.
4.97 stars / 29 Reviews
Airbnb “guest favorite”
Superhost
Why you’ll love it:
- Walk downstairs for coffee and breakfast at Krankie’s.
- The host’s attention to detail (Bluetooth speaker, Netflix, kitchen amenities, $5 gift card to Krankie’s Coffee, wine).
- Within walking distance of restaurants, coffee shops, and bars.
- Guests say the online photos don’t do the flat justice.
Rustic Loft in the Winston-Salem Arts District
Enjoy views of the downtown Winston-Salem skyline from this rustic loft in the center of Winston’s art scene. Many guests have used the space for weddings and photos.
Note: Guests say the four flights of stairs may be difficult for some people to navigate.
4.94 stars / 93 Reviews
Airbnb “guest favorite”
Why you’ll love it:
- It is located above a gallery and is perfect for those exploring Winston’s art scene.
- Within walking distance of restaurants, coffee shops, and bars.
- The loft is spacious, beautifully decorated, and has natural lighting, perfect for taking photos.
- Guests say the space is bigger in person than it looks in the photos.
The Camel City Lofts
If you’re looking for a place to stay in downtown Winston that will accommodate many people, check out this Airbnb! It’s 4,000 square feet with five bedrooms, three bathrooms, two kitchens, and an 800-square-foot deck that overlooks the city! If you like this location but need a smaller space, check out The Oasis at Camel City Lofts.
4.95 stars / 20 Reviews
Airbnb “guest favorite”
Superhost
Why you’ll love it:
- The spaciousness of this Airbnb makes it great for groups. Guests mention using it for team retreats, family reunions, and bridal parties.
- The loft is just steps away from restaurants, coffee shops, and bars.
- Although it’s up a flight of stairs, the living space is all on one floor.
Loft in Innovation Quarter
Stay in this 1930s building, remodeled as a unique loft, in downtown Winston-Salem’s popular Innovation Quarter.
Note: Since it’s in a busy part of downtown, there is a decent amount of noise from traffic and the nearby restaurants.
5.0 stars / 51 Reviews
Airbnb “guest favorite”
Superhost
Why you’ll love it:
- The host goes over and beyond, providing comfort and extra amenities not found in other Airbnbs.
- Excellent downtown location in Innovation Quarter, perfect for walking to restaurants, bars, breweries, etc.
Salem Town Hall, National Register of Historic Places
Talk about a unique, historic property! Listed on the National Register of Historic Places, this Airbnb served as Salem Town Hall from 1912 to 1926 and Fire Station Number 2 from 1926 to the 1970s. It has unique features, like a lofted library space.
Note: Although the listing says the space sleeps four, some guests feel it’s better suited for three people.
4.82 stars / 11 Reviews
Why you’ll love it:
- A spectacular, clean, and open space in one of Winston’s most unique historic buildings.
- The location is in Brookstown, a quieter area of downtown Winston-Salem with less traffic and noise.
Columbian Heights Room in the Historic Ludlow House
The Columbian Heights room on the second floor of the Ludlow House is in a charming and historical Winston-Salem neighborhood near downtown. The Airbnb has historically inspired décor and gorgeous stained-glass windows that offer views of Summit Street, St. Paul’s Episcopal Church, and 5th Street.
5.0 stars / 6 Reviews
Airbnb “guest favorite”
Superhost
Why you’ll love it:
- The historic home is an easy walk to a few of the best restaurants, bars, and shops in downtown Winston-Salem, including Mozelle’s, The Old Fourth Street Filling Station, Bernardins, Joyners Bar, and Vintage Sofa Bar.
- The stay includes breakfast at the Schaffner Inn.
- Guests say the room is immaculately clean and comfortable. The home’s unique aspects include the arched doorways and stained-glass window design.
Downtown Winston Speakeasy Condo
The 1920s speakeasy character of this two-bedroom condo in downtown Winston-Salem makes it a unique choice! Unlike other Airbnbs downtown, we love that this one offers privacy in a hidden, gated location.
Although it’s a new rental with no reviews, the host has 150 reviews on other properties.
Luxurious, Historic Home
This Airbnb is ideal for large families or groups of friends. It offers luxurious furnishings and antique touches that make you feel like you’re staying in an upscale hotel without the price and lack of privacy.
4.89 stars / 93 Reviews
Airbnb “guest favorite”
Superhost
Why you’ll love it:
- The historic home is an easy one-mile walk from downtown.
- Modern, spacious, and well-stocked, this rental is ideal for groups.
- The location is safe, convenient, and quiet.
Vintage Grocery-now Artsy downtown Apt near UNCSA
This apartment is in the front half of a 1920s grocery store. The unique space has been renovated and restored. The New York loft feel on the ground level has large storefront windows that let in a lot of natural light.
5.0 stars / 52 Reviews
Airbnb “guest favorite”
Superhost
Why you’ll love it:
- This Airbnb is a fun and eclectic vintage gem with loads of history.
- The location is near Old Salem but is a quick drive to downtown Winston-Salem. Guests say it’s the perfect spot for visiting Winston.
- Guests rave over this Airbnb, saying it’s a beautiful, comfortable space that reflects the overall vibe of Winston’s art scene.
