Guesthouse vacation rentals in Winston-Salem

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Top-rated guesthouses in Winston-Salem

Guests agree: these guesthouses are highly rated for location, cleanliness, and more.

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Top guest favourite
A private deck area is shown, featuring wooden decking and two metal chairs surrounding a small table. Green trees provide a natural backdrop, while wall-mounted lights enhance the space's functionality during evening hours.
Guesthouse in Greensboro
4.98 out of 5 average rating, 219 reviews

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.

Top guest favourite
A warm, inviting sleeping area is featured with a spacious bed adorned with a multicolored quilt. Nearby, a small table and chairs are positioned under a window, allowing natural light to illuminate the space. Framed artwork and floral curtains enhance the decor.
Guesthouse in Greensboro
4.97 out of 5 average rating, 421 reviews

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.

Top guest favourite
A spacious sleeping area features a neatly made bed adorned with patterned cushions. Soft natural light filters through a window, illuminating the room's blue walls and enhancing the wooden flooring. A small lamp and framed artwork are positioned on the wall, contributing to the overall comfort of the space.
Guesthouse in Kernersville
4.88 out of 5 average rating, 103 reviews

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.

Guest favourite
A cozy studio space is featured with a queen bed adorned in white bedding and accent pillows, accompanied by a decorative throw. Natural light filters through a window alongside a neutral-toned dresser and wall art, adding simple elegance to the inviting atmosphere.
Guesthouse in Kernersville
4.95 out of 5 average rating, 123 reviews

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.

Top guest favourite
A kitchen counter is visible, finished in a light stone material, paired with a mosaic tile backsplash. A glass kettle rests on the counter. The adjacent living area features a wooden cabinet and a television mounted on the wall, with natural light entering through windows.
Guesthouse in Greensboro
4.95 out of 5 average rating, 185 reviews

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.

Top guest favourite
A spacious outdoor area is surrounded by colorful autumn foliage, featuring two distinct buildings. One structure is a single-story unit with a covered entrance, while the other is a two-story building with large windows. A sign in the foreground indicates that pets are welcome and there are no cleaning fees.
Guesthouse in Clemmons
4.96 out of 5 average rating, 252 reviews

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.

Top guest favourite
A comfortable living space features a small round table accompanied by two chairs and a kitchenette in the corner. A spacious bed is visible, with soft bedding draping over it. Natural light enters through the windows, and a full-length mirror is mounted on the wall.
Guesthouse in Ardmore
5 out of 5 average rating, 60 reviews

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.

Top guest favourite
The exterior of a charming efficiency apartment is shown, featuring a covered porch with a welcoming sign. Lattice work accents the porch, while a small stone path leads to the entry. Lush greenery surrounds the building, enhancing its inviting appearance.
Guesthouse in Germanton
4.96 out of 5 average rating, 514 reviews

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.

Superhost
A spacious room features a comfortable queen bed with decorative pillows, alongside a small dining table set with bowls. A colorful area rug covers the floor, while a ceiling fan and art adorn the walls, enhancing the room's distinct character.
Guesthouse in High Point
4.79 out of 5 average rating, 156 reviews

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.

Top guest favourite
The spacious suite features a queen bed with a patterned bedspread, complemented by a cozy love seat and two accent chairs. A flat-screen TV is mounted on the wall, and decorative elements include a colorful door and a wooden accent wall. Natural light enters through the window and sliding door.
Guesthouse in Greensboro
4.97 out of 5 average rating, 470 reviews

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.

Guest favourite
The kitchen features stainless steel appliances, including a refrigerator and stove, alongside a wooden countertop. Open shelving displays dishware and cookware against a light wall. A decorative area rug adds warmth to the wooden floor.
Guesthouse in Mocksville
4.97 out of 5 average rating, 134 reviews

“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!

Top guest favourite
The entrance to the cottage features a small porch with two rocking chairs set against a green exterior. Red accents are visible on the door, and the area is surrounded by lush greenery and colorful flowers, providing a serene outdoor space.
Guesthouse in Lexington
4.98 out of 5 average rating, 435 reviews

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

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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