Apartment holiday rentals in Winston-Salem

Apartment in Downtown Greensboro

4.98 out of 5 average rating, 323 reviews

Downtown Remodeled 1906 Queen Anne

Only a few blocks from Tanger Performing Arts Center & 10 min drive to Coliseum and Aquatic Center. Plus, downtown is a walker's dream--craft breweries, restaurants, Civil Rights Museum, grocery, shops & more. Perfect for families & visiting, our downtown private apt is the entire 2nd floor with full kitchen, plus Wi-Fi & premium TV. Separate entry, front porch swing on a quiet dead-end street. Enjoy a walk downtown, and then relax & enjoy your privacy in comfort in a quiet neighborhood setting.

Apartment in Pilot Mountain

4.98 out of 5 average rating, 161 reviews

Downtown loft with a view of Pilot Mtn

The Cardinal Getaway is nestled in the heart of downtown Pilot Mtn. You can overlook local events from the patio or windows. You can walk to local shops and restaurants. If it's the outdoors, you crave you are just minutes away from the iconic Pilot Mountain as well as other outdoor activities. You will be staying in a historic building that has been renovated into a beautiful two-bedroom loft style apartment. It has a full bath, living room, kitchen, dining, laundry & new Mattress as of 2025.

Apartment in Winston-Salem

4.95 out of 5 average rating, 134 reviews

K-Obscura, Romantic Downtown loft

Historic loft in Downtown Winston Salem's Innovation Quarter. Located above Krankies Coffee near WFB Medical School and Bailey Park.Short walking distance to several restaurants and bars. This space has private entrance and patio. Includes gift card for coffee at Krankies. Note there is a train that passes by a few times a day and at night. We do allow pets but have a fee. Includes deep soaking tub, mini-kitchen and comfy king-size bed. Space is accessed via stairs. Parking included.

4.99 out of 5 average rating, 151 reviews

Tranquility Retreat

Welcome to Tranquility, a studio apt. with Tesla EV charging station. Our cozy (perfect for 1-2 guests), ~300 sq ft well appointed studio is located above a detached garage (with an ultra quiet garage opener) w/separate entrance on the same property as our single family home in Old Irving Park in Greensboro. Enjoy complete privacy in a safe, quiet, wooded setting and still be close to restaurants and shopping. Ample parking in the driveway or on the street. We're pet friendly too!

4.88 out of 5 average rating, 164 reviews

Apartment in Summerfield

Cozy Apartment on Mini Farm!

Our space features a queen bed & two sleeper chairs, TV w/ Roku, full kitchen, & bath w/ walk-in tub. This is a MIL apartment attached to our house on 9.5 wooded acres. It is NOT outfitted for children. SMOKING/VAPING IS NOT ALLOWED ANYWHERE ON THE PROPERTY. Long term stays welcome! Convenient to the Triad and points beyond. It's safe & quiet, & you can roam most of the property. Multiple security cameras outside. NEW: Fenced-in yard for off-leash playtime for your dog!

4.96 out of 5 average rating, 245 reviews

Charming Apartment in Historic Home near Downtown

Quirky apartment in 1902 house in Historic Dunleath district. An easy walk to downtown, restaurants/breweries, baseball stadium. Perfect location on a quiet street of homes from the late 19th and early 20th century. Private apartment with separate entrance. One queen bed and a pull out queen sofa (in a separate room). All linens are line-dried and fragrance-free. Full kitchen with all the necessities. Outdoor patio with table and chairs. Free street parking.

Superhost

Apartment in Ardmore

4.82 out of 5 average rating, 701 reviews

Cabin apartment in West Salem

Welcome to Winston-Salem! This Apartment is on the LOWER level of my log cabin and sits a mile from downtown! All new appliances and newer mattresses! Cute, and basic for what you will need. Sound travels, so you might hear the upstairs guest walking from time to time. The unit includes two bedrooms with two queen beds with a living room , bathroom and kitchen with its own entrance. I think you will enjoy the space! Any questions please reach out!

Apartment in Winston-Salem

4.97 out of 5 average rating, 113 reviews

Horizons @ Summit - 2 Kings in Downtown Winston

Your Downtown Winston-Salem Retreat, with the comforts of home and the convenience of being near the best that our city has to offer! Enjoy your stay in our renovated and professionally designed apartment, while having the perk of in unit laundry, high-speed internet, dedicated work space, 2 full bathrooms and a fully stocked kitchen. Smart TVs, black-out curtains, and room to unpack your bags and stay awhile, make your stay even more like home.

4.97 out of 5 average rating, 269 reviews

Private Arts & Crafts Charmer Near UNCG, Downtown

Private 1920s Arts & Crafts charmer in historic Westerwood district with keyless entry. Perfect location in a friendly, tree-filled neighborhood. Adjacent to UNCG & Greensboro College. Walking distance to Tanger Center, downtown restaurants, bars, museums, and shopping. Centrally located so easy to get to the International Civil Rights Museum, Coliseum, Science Center, A&T University, Children’s Museum, & pretty much anywhere in the Triad.

4.92 out of 5 average rating, 274 reviews

1906 Classic Retreat - Entire Apartment

Welcome to Classic Retreat! This is the Airbnb for QUIET guests. The apartment is all yours with bedroom, living room, private bath and kitchenette. All the tech you need with wireless charging, 2 smart TVs and fiber optic cable wifi. Decor with flavors from Italy. Great for romance, rest or work. 1 mile from downtown. 1 block from UNCG and Greensboro College. 2 miles from Greensboro Coliseum and Greensboro Aquatic Center.

Apartment in Winston-Salem

4.95 out of 5 average rating, 288 reviews

West Salem Art Hotel, "Art"partment #1

Welcome to the West Salem Art Hotel! This eclectic and beautiful apartment is located in a 1931 historic brick building only 1 mile from Downtown Winston-Salem! All the conveniences of staying JUST on the outskirts in Historic West Salem, without all the city noise, AND located in the middle of a peaceful urban garden! We are minutes away from the best eateries/entertainment W-S offers! Private, unique, and clean.