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.

Kevin's Home

Enjoy your stay in this spacious 2-bedroom, 2-bath home nestled in a peaceful neighborhood just minutes from Winston-Salem. This quiet retreat offers comfort and convenience with easy access to major highways, local shopping, and popular eateries. The fully equipped kitchen makes dining in a breeze, while each bedroom provides a cozy and restful space. Whether you’re visiting for business or leisure, you’ll appreciate the home’s blend of tranquility and accessibility. Come make yourself at home

Quiet Clean 4BR pet friendly in town Large lot

Welcome to your Ultimate King getaway! Perfect for wedding groups, hiking families and out-of-town workers seeking space, privacy and convenience. Nestled on a sprawling 1.75 acre lot with a 1860 square foot. This spacious home offers a perfect blend of small town tranquility, and big city access. Whether you are gathering the family for a local wedding, hiking the local mountain trails, or traveling for business, our home boasts all the space you need. Please note we do not allow Parties

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.

Premium Retreat close to WFU w/ Lvl 2 EV Charger

Exceptional , award winning property offering unparalleled convenience and comfort for a premium short term stay close to Wake Forest campus area. This newer professionally furnished, 1495 SF, single dwelling, 2 story home has 3 bedrooms, 2.5 bathrooms. Features: Level 2 EV Charge Station, walk in tile shower, Easy All in One Washer/Dryer unit, Fast Internet and more. Great for 2 or 3 couples. 1 King, 2 Queens. All Bedrooms are on 2nd Floor. Max 4 cars & 6 Guest. No Smoking and No pets.

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.

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.

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!

Lakota Rock Cabin

Beautiful new 1 bedroom cabin. Covered porches on front and back. Sleeps 4 (queen bed and pullout sofa). Conveniently located 10 minutes from Pilot Mtn State Park, 20 Minutes from Hanging Rock State Park, 20 Minutes from Dan River, 20 minutes from Mt. Airy (Mayberry), 25 minutes to Winston-Salem. Direct access to the Sauratown Horse Riding Trails (located at section 9 of the trails).