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.

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.

Private, Peaceful, Green Hideaway 6 Minutes to WFU

Just minutes from Wake Forest, we have a completely remodeled this very special place. We have often stood at the huge windows of this ground level space and watched mother deer with their fawns play in the yard. Your home away from home is at the end of an already quiet cul-de-sac so traffic noise is zero. Your suite is completely private with its own ground level entrance. Your kitchen has a full size sink, an induction stove, fridge, with all your cookware, dishes. New bath with tub.

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.

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.

Stony Knoll Vineyards Wine Lodge

A family heritage 1850 log home that was completely renovated in 2007. The front porch overlooks Stony Knoll vineyard grounds and tasting room which is across the street. This wine lodge consists of 1 full bath with a shower and jacuzzi, 1 double bed, 1 king bed and 1 single bed loft. A fully furnished kitchen for all meal prep. A full sized living room with fireplace and TV. Come and enjoy a glass of wine on the front porch or listen to the rain hit the country tin roof.

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.

Country View Getaway

This home is a perfect central location between both the Blue Ridge Parkway and the Sauratown Mountains. Only 15 miles from Hanging Rock. Only 2.8 miles from Pilot Mountain State Park's Grindstone Trail. Jolo Winery is just 4 minutes away and 14 minutes from Shelton Vineyards. Located on a 40+ acre farm, there are plenty of areas to explore, from the donkeys at the stable to multiple breathtaking views throughout the property.

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.

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.