Summit Street Inns 
1 bedroom | 1 bathroom 

Stay in one of two restored historic homes on the edge of downtown. The Ludlow House features beautiful stained-glass windows, while the neighboring Sheppard House offers the same elegant charm. In each of the 10 bedrooms across properties, guests will enjoy plush robes, luxurious bathrooms, and a complimentary breakfast. 

What Visitors Say: “What a special place! The combination of deep history with quirky/unique decorations everywhere gives you more to see the more you look. The rooms are quiet, well-appointed, and each one is different…The full breakfast is amazing, different each day, and a glass of wine each evening…” 

“Wieners & Losers” – 80s Arcade in Pfafftown 
1 bedroom | 1 bathroom 

Step into a 1980s time capsule at this retro-themed stay featuring the largest private collection of working golden-age arcade games on the East Coast. The bedroom is packed with vintage décor, a 1986 Magnavox stereo, classic consoles, and more fun surprises. You’ll have a private entrance, your own kitchen, and a dedicated bathroom. 

What Visitors Say: “Absolutely amazing and entertaining authentic 80s decor and working entertainment options. This will take you back to the golden 80s era (and yes I grew up in the 80s - so I know)...worth the price and we enjoyed every minute!” 

Chateau Bergeron at Medaloni Cellars 
1 bedroom | 1 bath 

Designed for couples, Chateau Bergeron offers a quiet retreat on the grounds of Medaloni Cellars. Stays include a complimentary bottle of wine and branded glasses to take home, plus the opportunity to explore the vineyard. Adventurous guests can also book the secluded TreeHouse, accessible only by All Wheel Drive or 4x4 vehicle. 

What Visitors Say: “Each weekend I go, I truly feel like I'm home. I also had the privilege to stay at 2 of their cabins, and it was just an amazing experience. I recommend this place to anyone!” 

The Red Door Cabin 
1 bedroom | 1 bathroom 

Tucked into the woods, this modern cabin offers a secluded, pet-friendly stay. Enjoy the peace and quiet of this new space with granite countertops and a beautifully tiled shower while you're still only a 10-minute drive to downtown Winston-Salem and 1/2 mile to I-74. 

What Visitors Say: “Very nice cabin! Convenient to shopping and restaurants yet so quiet and peaceful. We stayed here…and loved how clean and homey this was. The cabin smelled new and was filled with wonderful light from all the windows.” 

The Man Cave 
1 bedroom | 1 bathroom 

This garage apartment features multiple “man cave” amenities with a pool table, dartboard, and a 50-inch TV. The detached space has its own entrance and sits in a walkable neighborhood close to Wake Forest University and downtown. 

What Visitors Say: “We enjoyed our stay so much. The apartment is full of things to do, clean and cozy. The king size bed was amazing. Would love to stay there again when we are back up that way. There isn’t anything we would change. Perfect getaway.”

Tiny Barnside Escape 
2 lofts | 1 bathroom 

Great for families with young kids, this tiny home lets nature in with big windows and plenty of outdoor space. Guests can roam 32 acres, gather at the fire pit, or play bocce and three-hole frisbee golf. Belews Lake is popular for boating and fishing and is located just a few miles away. 

What Visitors Say: “Absolutely perfect little getaway cabin! Super clean, cozy, and thoughtfully put together — everything we needed for a relaxing escape. We’ll definitely be back!” 

Movie Magic: The Scene Stealer 
3 bedrooms | 2 bathrooms 

Settle into leather theater seats and watch your favorite films on a 75-inch TV at this cinema-themed retreat. The home is filled with movie-inspired decor and sits in a quiet neighborhood on the southern side of town. 

What Visitors Say: “This place was so fun if you’re a movie fanatic! From the wall paintings to the pictures hanging in the hallway & all rooms in the house. Movies & movies are everywhere! And the living room is set to the perfect movie theater style with fancy recliners & a big comfy couch!” 

Downtown Condo with Private Library 
2 bedrooms | 2 bathrooms 

Book lovers will appreciate this condo’s private library and its blend of classic and industrial style. Statement chandeliers and a clawfoot tub offer elegant touches, and it’s in a prime location, easily walkable to downtown restaurants and entertainment, as well as Old Salem. 

What Visitors Say: “This condo is perfect! There is plenty of room so you don't feel on top of each other. The kitchen is great, if you are a foodie and if not, there are countless great restaurants around. The bathrooms/bedrooms are comfortable and welcoming… It is a pure delight! You will love your time here, as we did.” 

Black Bear Cabin 
3 bedrooms | 2 bathrooms 

Black Bear Cabin offers a mountain-style escape just 20 minutes from downtown and minutes from groceries and other necessities. A dedicated game room, complete with Pac-Man, a pool table, and board games, keeps kids entertained. Outside, a large deck, grill, dining area, and fire pit with Adirondack chairs make it the perfect place to relax after a day of exploring. 

What Visitors Say: “My stay was excellent from start to finish. The place was clean, comfortable, and exactly as described…The location was convenient, the environment was quiet, and the overall experience was truly relaxing. I would definitely stay here again and highly recommend this Airbnb to anyone looking for a smooth, stress-free visit.” 

The Dogwood Cottage 
2 bedrooms | 2 bathrooms 

This renovated bungalow offers a luxurious stay where no details were spared. There are two master suites—one featuring a clawfoot soaking tub and the other a spacious rain-head shower. The kitchen will make any chef swoon, and the location makes exploring easy. Old Salem is less than half a mile away, and downtown is just over a mile. 

What Visitors Say: “An amazing gem of a place. 5-star host…and we had a 5-star stay…Close to great restaurants and shopping. The house has a loving feeling of home. Comfortable and peaceful and we had everything needed from check in to check out…” 

The Mulberry Cottage 
2 bedrooms | 2 bathrooms 

The Mulberry Cottage is immaculately decorated in bright, modern farmhouse style and has an open-concept layout that’s perfect for gathering. An outdoor seating area offers views of the city skyline from the southern side of downtown. 

What Visitors Say: “Enjoyed our stay at Mulberry Cottage. It was just as described - clean, cozy and wonderfully decorated. Appreciated the small thoughtful gestures. We look forward to staying here again on our next visit!”

West Salem Art Hotel 
6 bedrooms | 6 bathrooms 

West Salem Art Hotel offers a creative stay where every suite or apartment has its own personality, from the flower-filled Rose Room to the VHS Room stocked with 400 tapes. Shared lounges make it perfect for group getaways, and art covers the spaces, with many pieces available for purchase. You can also rent individual rooms through Airbnb. 

What Visitors Say: “My bridesmaids and I stayed here before my wedding and had an absolutely wonderful time! Every little piece of decor and art is so well thought out and perfectly placed. I cannot imagine having stayed at a more perfect location. The beds were extremely comfortable, and all of our rooms were unique…” 

Mansion on Main in Old Salem 
4 bedrooms | 3.5 bathrooms 

A restored 1873 landmark and the largest home within Old Salem, Mansion on Main blends elegant period details with modern comfort, from its sweeping curved staircase and ruby-stained glass to soaring ceilings. A chef’s kitchen with a French Lacanche range and optional private catering makes it ideal for refined gatherings. 

What Visitors Say: “WOW. Really, just wow. This is such a gorgeous, funky and beautifully designed historic home with some modern and eclectic art/design. Each room is beautifully curated with such personality. We wish we had stayed longer!” 

West End Historic Home 
5 bedrooms | 3.5 bathrooms 

This stay will appeal to anyone who loves historic charm, as it’s set in a 1916 home filled with antique furnishings, from the sofas and light fixtures to the hutch in the dining room. It’s situated in the West End neighborhood across from Grace Court Park, near many popular restaurants and breweries. 

What Visitors Say: “This is a beautiful older home in a lovely neighborhood. It's very walkable to downtown and other areas, such as Hanes Park…The home has plenty of room for lots of guests, with several areas for gathering together.” 

West End Retreat with Pool, Sauna, & Hot Tub 
6 bedrooms | 4 bathrooms 

Another option in the West End neighborhood, this historic home feels like a high-end retreat thanks to its heated saltwater pool, cedar barrel sauna, and hot tub. The house is over 100 years old, but the interior is tastefully decorated and furnished, allowing you to settle in and feel right at home. 

What Visitors Say: “Can’t say enough about our stay…House was incredibly beautiful and so lovely decorated. Everything was pristine…It was like having a “spa” retreat with all the amenities - pool, hot tub, sauna.  Exactly as described but even better…” 

There are many other places to stay in Winston-Salem from historic & boutique hotels to national brands. For a full list, see our hotels & places to stay directory or request a free Visitor Guide.