
Guesthouse vacation rentals in Winston-Salem
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouses in Winston-Salem
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.

Gate House Garden
Walk down the path to your mini suite: a cozy studio with an open floor plan, kitchenette (microwave & toaster over), clawfoot tub with shower, queen bed, & private deck. Great for 2 guests or place to work remotely. A 5-min walk to scenic lake/trails. In a very quiet neighborhood, it's not a good fit for gatherings or folks coming & going at all hours. Please no smoking/vaping of any kind in/on premises. 10 min drive to GAC, Tanger, UNCG, A&T, Coliseum, Guilford College & 25 mins to High point.

Stylish Hamilton Lakes Studio Facing Park/Trails
Private keyless entry to 2nd floor garage studio apartment in prestigious Hamilton Lakes. Space is one large room with a kitchen w/bar next to living area. Sleeps 4 (2 under 18) with queen bed, a twin and a sofa; 42" TV, SMART bluray, WIFI, NETFLIX, toaster oven, coffee maker, microwave, fridge, full bathroom with walk-in shower; washer/dryer in garage. Three miles of trails start across the street; 5 minute walk to the lake/playground. 3rd & 4th guests (must be under age 18) $20 each/night.

Cozy Downtown Kernersville Carriage House
Historic hideaway located behind a private home in a gated lot in downtown Kernersville. Hit the sidewalks and walk to multiple restaurants, seasonal Farmer's Mkt, downtown shopping, bars, coffee shops, parks, and the Botanical Gardens! Easy access to I-40 (.5 miles away), 15 mins to PTI airport and Winston-Salem. House has 2 two flights of stairs. Please read add'l notes. 3 reviews minimum required to book. 5 night minimum during Furniture Market. Distance to hospitals 3.5- 18.5 miles.

The Bungalow at Weather Ridge
Kick back and relax in this calm, stylish space! Our private guest house is the perfect studio style space. COMFORTABLE queen bed, plus a futon for 3rd guest, dining, loveseat, full micro kitchen and full bathroom are all beautifully designed for your stay. Located at the back of acre lot in quiet, well established, neighborhood. Centrally location in the Triad: 10 minutes from Kernersville, 12 minutes from Winston Salem, 20 minutes from Greensboro, and 25 minutes from downtown High Point.

Leafy, Suburban Abode
Spacious 2nd story private apartment located in tree-lined, bucolic neighborhood of Carriage Hills. Well lit with natural light, breakfast counter, and ample closet space. Cable TV and high speed internet included. -Apple TV (your subscription) Washer/dryer, full size refrigerator/freezer, small space oven, dual stove burners, and good size great room to relax. NO CATS ACCEPTED! Dogs (<40) accepted with $75 fee for the first 2. Host documented approval if bringing more.

Bee Happy- Studio & Pets Welcome- No cleaning Fees
Welcome to the "Bee Happy" a self-check in retreat for anyone needing a clean, peaceful retreat to rest a weary head, visit locally or just get away from it all. Pets are always welcome and are as pampered as our guests (Please read our important Pet Policy below). Our large, private outdoor deck is complete with a small side yard and fenced for your pet's safety. Our neighborhood is beautiful, secluded and in a perfect location that is close to I-40, Parks, restaurants.

Rosewood Carriage House
Enjoy a relaxing stay at this peaceful and centrally-located space. Cannot beat location! Only a 1/2 mile from Atrium WFU Baptist Medical Center, 3 miles to WFU and Reynolda Village, minutes from downtown and Forsyth Medical Center. Walkable to Thruway shopping center restaurants and shops. Fully equipped kitchenette, brand new bathroom, and king size bed with luxury bedding. The private back patio feels cozy and secluded even in the middle of a bustling neighborhood.

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.

Carolina Cowgirl Cottage
Charming cottage, newly refurbished. Cozy space w/full kitchenette, breakfast table, full bath w/shower, TV- seating area, queen bed with vaulted ceiling, professionally decorated. Pet OK w approval. walkable historic Emorywood & HP Country Club neighborhood, near HPU, hospital, park, HP Library, farmers market & HP Furniture Market. Big yard, patio & gas BBQ. Week-longterm discount. 1111 Orlando Place.

Private Guesthouse in a Quiet Neighborhood.
If you are looking to party, this is not your place. Our lovely and cozy detached suite is in a quiet residential neighborhood close to the charming restaurants and shops of Friendly Shopping Center. A short 13 min drive to downtown Greensboro and a short 12 minute drive to the Greensboro Airport. Perfect for tourists or business travelers who want to be able to see all Greensboro has to offer.

“Home” on the Road!
Have fun with the whole family at this stylish apartment situated on a beautiful 3.5 acre property! Massive walk in tiled shower with multiple shower heads. Friendly dogs allowed for $35 a dog. No more than 2 dogs. Must be left in a crate if left in apartment alone. We have a large crate available to use. We have a SUPER friendly 2 year old poodle/border collie mix that will greet you!

The Cottage
Located in the historic district in Lexington, NC, "The Cottage" is a backyard studio apartment set in a beautiful garden surrounded by a privacy fence. Only blocks from the picturesque uptown we are also in a town famous for barbecue. We are about 30 min. from Winston-Salem, Greensboro, the NC Zoo and the Charlotte Speedway, and serve as a great place for your vacation headquarters!
Popular amenities for Winston-Salem guesthouses
Family-friendly guesthouses

Tranquil & Private Loft in Charming Starmount

Peaceful Place

The Friendly Place

Ooh La La Serene Private Basement Apt!

Peaceful retreat for adventure seakers

The Cottage at Haze Gray Vineyards

The Stratford Guesthouse

Sunset Hill Pastures
Guesthouses with a patio

3 mins from Downtown - PS5, King Bed & EV Charger

Ardmore Private In-Law Suite/Apartment

Adorable Spacious Studio w/ Full Kitchen near HPU

Entire Private Entrance Studio Apartment with Pool

Tranquil and private lower level apartment

The Little White House

The Bunkhouse at Olde Stone Farm

Secret Garden cottage on Queen St.
Guesthouse rentals with a washer and dryer

Golden Studio, few minutes to Downtown.

✩✯10min→ TOP Dine+Shop | 500Mbps | Netflix | Yard

Backyard Pool House

The Fiddling Frog Guest House

Guest House at Tall Tree Manor

Pickleball and Privacy

Jamestown 1 Bedroom

Luxurious guesthouse with gorgeous pasture views
Quick stats about guesthouse rentals in Winston-Salem

Total vacation rentals
Explore 20 vacation rentals in Winston-Salem

Nightly prices starting at
Winston-Salem vacation rentals start at $42 CAD per night before taxes and fees

Verified guest reviews
Over 1,170 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Winston-Salem vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winston-Salem rentals

4.8 Average rating
Winston-Salem stays are highly rated by guests—averaging 4.8 out of 5!
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- North Carolina Zoo
- Wet'n Wild Emerald Pointe Water Park
- Hanging Rock State Park
- Pilot Mountain State Park
- High Meadows Golf & Country Club
- Sedgefield Country Club
- Dan Nicholas Park
- Meadowlands Golf Club
- Stone Mountain State Park
- Greensboro Science Center
- Old Town Club
- Lake Norman State Park
- Divine Llama Vineyards
- Mooresville Golf Course
- Starmount Forest Country Club
- Lazy 5 Ranch
- Roaring Gap Club
- Olde Homeplace Golf Club
- International Civil Rights Center & Museum
- Gillespie Golf Course
- Raffaldini Vineyards & Winery
- Childress Vineyards
- Shelton Vineyards
- Guilford Courthouse National Military Park




