Whether you’re looking to visit Winston-Salem in style for the weekend or are a local in need of an unforgettable staycation, we’ve compiled a list featuring 15 extraordinary rentals in the Twin City that are worthy of a trip for you, your partner, your bestie, or the whole squad this year.
Just a heads up: Prices may vary depending on dates selected, taxes, and booking and cleaning fees (sorry, Airbnb and Vrbo make the rules, we just follow them).
Historical stays
Spacious historical home
This guest favorite is just three minutes from downtown in the Washington Park neighborhood.
- ~$203 a night
- 4 BD | 3.5 BA
- EV car charger, washer/dryer + fast Wi-Fi
Historic beauty
The renovated 1920s home across the street from Hanes Park has modern updates.
- ~$300 a night
- 5 BD | 7 BA
- Enclosed sun porch, supplies for young children + indoor fireplace
Remodeled historic home
Walk to Old Salem or explore the West Salem neighborhood from your cozy 1920s bungalow.
- ~$175 a night
- 2 BD | 2 BA
- Washer and dryer, linens provided + private back patio
For the outdoor lovers
Courtyard cottage
This guest house studio near Truist Stadium has a private outdoor oasis that is perfect for pets, which stay for free.
- ~$85 a night
- 1 BD | 1 BA
- Fully fenced-in courtyard, water features + dedicated workspace
Cozy Ardmore bungalow
Learn why locals love this centrally located neighborhood in this home filled with plants and art.
- ~$135 a night
- 2 BD | 2 BA
- Stone patio with gas grill and fire pit, street parking + pets welcome
Cozy King Blue H2O Staycation
This spot off South Main Street is five minutes from downtown and lots of outdoor amenities.
- ~$181 a night
- 1 BD | 1 BA
- Hot tub, firepit, double hammock + stock tank pool
Log cabin dreams
Cabin in Ardmore
The upper level of this custom cabin will make you feel like you’re miles away from the city even though you’re less than a mile from downtown.
- ~$89 a night
- 2 BD | 1 BA
- Pets allowed, linen essentials included + private entrance
The Red Door Cabin
Escape to the woods in this stylish cabin, which is just 10 minutes from downtown.
- ~$189 a night
- 1 BD | 1 BA
- Pets allowed, washer and dryer + self check-in via keypad
Majestic Getaway Cabin
This 1930s cabin is nestled down a private drive but is a mile away from Wake Forest University.
- ~$295 a night
- 3 BD | 3 BA
- Fully equipped kitchen, washer and dryer + large porches
Places for the whole family
The Zen Ranch
This fully remodeled home near Clemmons has an open floor plan with plenty of space to spread out.
- ~$169 a night
- 3 BD | 3 BA
- Ample parking, exercise equipment + private patio
Spacious home with deck
Walk to Reynolda Gardens in this fully renovated, family friendly home.
- ~$124 a night
- 4 BD |2 BA
- Toys and games, outdoor space + pet friendly
Charming West Highlands home
Feel like a local in this Cape Cod-style home nestled between West End and Buena Vista.
- ~$162 a night
- 3 BD | 2 BA
- Fully stocked kitchen, fenced-in backyard with deck + washer and dryer
Easy to get around
Downtown Winston-Salem condo
This updated condo steps from restaurants and entertainment has a lofted library for the literary lover.
- ~$98 a night
- 2 BD | 2 BA
- Keyless entry, free street parking + open floor plan
The Cottage
Perfect for game days, this spacious and modern home is a short walk or drive to Wake Forest University athletic facilities.
- ~$85 a night
- 2 BD | 2 BA
- Outdoor patio, backyard games + pet friendly
Sanctuary
This professionally furnished condo near Clemmons is perfect for a romantic getaway.
- ~$80 a night
- 1 BD | 1 BA
- Indoor fireplace, patio + access to community pool and gym
Looking for more properties in the Twin City? Check out our guide to other unique places to stay.
