Holiday rentals in Tobaccoville

Bungalow on Broad Street near Winston-Salem

Just far enough away from the bustle of the city. Enjoy a unique experience, having the whole house/yard to yourself in our newly renovated and fully updated historic Craftsman style bungalow located outside of Winston Salem. 10 mins to Wake Forest University, 15 mins to downtown Winston Salem, Old Salem and School of the Arts. Convenient to Greensboro, close to vineyards, Pilot Mountain and Hanging Rock State Parks with access to hiking, biking, tubing, zip lining and other outdoor activities.

Sleepy Bee Cottage, simple charms, near WFU

Feels like the countryside within city limits. This cottage sits on shared property with the owners’ home and overlooks more than an acre of woodland, with a small garden just out front. Beyond the energized deer‑protection fence lies a Duke Energy easement and a wooded ravine, giving the property a quiet, tucked‑away feel. Guests have ample, well‑lit parking, along with access to a fenced dog yard. A small seating area beneath a mature dogwood tree offers a peaceful spot to relax.

The Rock Retreat

This beautiful log cabin, previously known as Indian Creek Cabin, has been an important part of the Hanging Rock Community for many years. It began as the Hanging Rock Outdoor Center. The property is adjacent to the Indian Creek Trail area. It is within a few miles of the Lower Cascade Falls, Dan River, Moore's Spring bike trails, and of course, Hanging Rock State Park. Adventure awaits with ziplining, kayaking, canoeing, and river tubing excursions within minutes of the front door.

Mel’s country cottage. Country life near the city.

Private detached effeciency apartment in a country setting near WinstonSalem. Queen bed, kitchenette with sink and essentials, sofa, smart TV, full bath, covered porch. Relax by the creek or enjoy nature walks. Watch the occasional deer & other wildlife. Use the grill or fire pit at your leisure. Pets welcome. Local restaurant & convenient store 1 min. away. Close to many tourist destinations- Hanging Rock, Winston Salem, Pilot Mt. Belews Creek power station.

The Joyful Loft Apartment! Private Studio Retreat

Welcome to the Joyful Loft, a stylish and private studio retreat designed for comfort and convenience. Nestled above the garage with its own dedicated entrance, this cozy space offers complete privacy while still being close to everything Winston‑Salem has to offer. The separate entrance and private staircase, make the loft feel like your own personal hideaway. The Joyful Loft combines style, convenience, and a welcoming atmosphere.

Hikers Nest At Pilot Mountain 4b/2b Entire Home

Experience mountain cottage living in a stunningly restored 1950’s home! A bright, comfortable base to call home while you explore Pilot Mountain State Park, Mount Airy, (home of Mayberry from the famous Andy Griffith Show), Hanging Rock State Park, romantic wineries, and life in a mountain town. Climbing, hiking, biking, and horse riding abound in this area. A perfect stay for a romantic getaway or a friends vacation.

Secluded cottage on 8 acres right outside of WS

Secluded cottage on 8 acres right outside of Winston Salem. It includes 1 closed off bedroom with a twin bed and pack n’ play if needed. There is a 2nd bedroom with a queen bedroom and TV. This cottage is a great place to come relax! We are close to a few wineries and breweries. Come enjoy the peaceful property by the outdoor fire pit and patio. Please note we have a stove and toaster oven but not a oven.

The Red Door Cabin

Kick back and relax in this calm, stylish space! This little cabin is brand new and nestled just inside the woods, but only 1/2 mile from I-74 and only 10 min. to downtown Winston Salem, NC. This little cabin was built just for short term guests, it has granite tops, stained concrete floors, a beautiful tiled/stone shower, and will surely help you unwind and enjoy your stay in this delightful space!

Rocky Knoll Hideaway | Visit Family | Quiet Escape

Welcome to Rocky Knoll Hideaway — your peaceful home base for visiting family, relaxing, and recharging. Tucked among the trees, this cozy private cottage offers the perfect blend of quiet seclusion and convenient access to the area. Whether you’re here for a weekend visit, a holiday stay, or just a break from the busy pace of life, Rocky Knoll Hideaway offers a warm, welcoming place to land.

Foothills Escape

Take it easy at this unique and tranquil getaway. Relax by the fire pit while you enjoy the beautiful view of Pilot Mountain. Just minutes to historic Mayberry or the shopping and theaters of Winston Salem. Whether you are looking to kayak at the nearby rivers, take in area wineries or see the sites… this slice of heaven is in the midst of it all. Don’t wait. Pilot Mountain is calling!

"Deacon House" 3 bedrooms

Looking for a place to stay in Winston Salem? Check out this 1,315 sqft. single family home that has 3 bedroom and 2 full bath. It has its own driveway with 2 car garage attached and fenced in backyard, guest occupy the entire house except the attic. It is just a few minutes away from downtown, Wake Forest University, Reynolda Garden, LJVM coliseum, Starbucks and grocery stores.

Treetop- 3 King Suites

Treetop is Stokes county's most luxurious vacation rental of its kind! This newly built home features three King suites so that everyone gets the privacy they want while away from home! Enjoy the outdoors while dining outside, getting cozy by the firepit, trying your hand at a little putt-putt, stargazing or just sitting back to enjoy the peace and quiet.