Guesthouse vacation rentals in Winston-Salem

A serene courtyard features a circular gravel path bordered by greenery and colorful plants. A brick wall with a classic outdoor fireplace stands nearby, accompanied by white lounge chairs for relaxation. A vibrant blue door leads into the studio, inviting guests to explore.

4.97 out of 5 average rating, 235 reviews

Tranquil & Private Loft in Charming Starmount

This tranquil & quiet studio is nestled in Starmount. The calming interior is perfect for relaxing and recharging your batteries. This loft boasts a king size bed, kitchenette, Wifi, 47" flatscreen TV for either watching in bed or lounging on the sofa. If you want to work, a desk is there for you to spread out. Relax in the gorgeous courtyard, dining area or in front of the fireplace. Better yet, enjoy the "secret garden". Perfectly located in central GSO which is close to shopping & downtown.

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A modern kitchen features sleek cabinetry and stainless steel appliances. A central island with barstools provides a casual dining space. Natural light enters through frosted glass doors, enhancing the bright and airy environment. A decorative plant sits atop the island, adding a touch of greenery.

4.99 out of 5 average rating, 186 reviews

Sunset Hills Carriage House! King Bed

Industrial Chić Abode in Beautiful Sunset Hills! Close to Everything with all the comforts of home. The Carriage House offers a private self contained guesthouse located behind our house ( 485 sq ft studio ) Safe upscale neighboorhood. Comfy King Bed! We have a pullout Queen sofa bed available for extra guests! 2 car max, NO SMOKING OR PETS! Walkable to UNCG and 2 minutes from everywhere you want to be! Close to Lindley Park favorites at the corner, UNCG, Downtown and Greensboro Coliseum.

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An electric fireplace is featured, showcasing a flame flickering against a backdrop of decorative logs. The sleek design adds a modern touch, while the warm glow creates a comforting focal point within the space.

4.93 out of 5 average rating, 164 reviews

The Downtown Loft Apartment

The Loft is a studio guest house in Downtown Greensboro. Thoughtfully furnished, comfortable, and immaculately clean and disinfected apartment in the heart of downtown. Lots of light and private. The electric fireplace adds to the cozy feel. Easy, independent check-in/out w/ electronic lock. This is a studio apartment with 2 beds--a queen sized murphy bed, and a full sized futon couch bed. It is best suited for singles, couples, or people that feel comfortable sleeping in the same space.

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A charming white cottage is featured with a bright blue door and large windows. A colorful rooster sculpture stands nearby, adding a whimsical touch to the well-manicured garden. A stone pathway leads to the entrance, surrounded by a low brick wall.

4.99 out of 5 average rating, 103 reviews

Foghorn's Roost

Delightful 1920's cottage in historic Westerwood neighborhood. Located right next to Lake Daniel Park featuring bike path, greenway, pickleball courts, and more. Five minute walk to UNCG, and five minute drive to downtown restaurants, breweries, the Tanger Center, the International Civil Rights Museum and much more. Recently renovated space with new cabinets, countertops, and appliances. Fully stocked kitchen and complimentary coffee and tea bar. Smart TV with all popular streaming apps.

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Guesthouse in Kernersville

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.

4.89 out of 5 average rating, 112 reviews

Cozy Downtown Kernersville Carriage House

Historic hideaway located behind a private home in a gated lot in downtown Kernersville. Walk to multiple restaurants, seasonal Farmer's Mkt, downtown shopping, bars, coffee shops, parks, and Botanical Gardens! Easy access to I-40 (.5 miles away), 15 mins to PTI airport and Winston-Salem. NO CHILDREN UNDER 12. House has 2 two flights of stairs. 3 reviews min. required to book. Please read add'l notes. 5 night min. during Furniture Market. Distance to hospitals 3.5- 18.5 miles.

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4.96 out of 5 average rating, 307 reviews

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

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.

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4.99 out of 5 average rating, 108 reviews

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

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.

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4.92 out of 5 average rating, 345 reviews

Guesthouse in Jamestown

Beautiful Duplex

PLEASE READ BEFORE BOOKING Maximum Occupancy: 2 GUESTS (Including Children) check in is at 3:00 PM. Check out at 10:00 AM. Enjoy a simple, peaceful stay in our centrally located duplex . We're just 15 minutes from UNC Greensboro, High Point University, the Greensboro Coliseum, Four Seasons Mall, Friendly Center, Piedmont Triad International Airport (GSO) and both Downtown Greensboro and High Point. Downtown Jamestown and Greensboro topgolf only 5 minutes away.

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A brick exterior home is surrounded by lush greenery, featuring an inviting front porch and well-maintained landscaping. The driveway leads to a spacious entrance, framed by neatly trimmed bushes and trees. The peaceful setting offers a sense of privacy on the wooded property.

4.99 out of 5 average rating, 105 reviews

Tranquil and private lower level apartment

Just relax! Come home to peace & quiet on this wooded 2 acre property. You’ll have no problem stretching out in this very large, yet cozy, day walk-out lower level apartment of the home. Enjoy the patio table for breakfast or dinner, or swing your cares away with cup of coffee or a glass of wine. This place is made to unwind from a long day. The friendly neighborhood is easy and safe to walk. 5 minutes from PTI airport, and an easy 20 minutes to downtown.

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4.96 out of 5 average rating, 554 reviews

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

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.

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A vibrant outdoor garden area features lush greenery and blooming flowers. Comfortable seating is provided with two chairs positioned on a stone patio. A charming garden studio is visible in the background, partially covered by climbing plants, creating a serene environment.

4.97 out of 5 average rating, 1358 reviews

A charmer! Great spot near downtown.

A sunny garden studio in peaceful Fisher Park historic neighborhood that's an easy walk to downtown, restaurants/breweries, baseball stadium. Perfect location. Private with a separate entrance. One queen bed. Wifi. Plenty of on street parking. The kitchenette area has a microwave, coffee pot (I provide coffee/tea & water cooler), mini fridge w/ sm freezer. Private outdoor garden area with table, chairs & umbrella.

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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.

4.97 out of 5 average rating, 507 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.

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Popular amenities for Winston-Salem guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

4.98 out of 5 average rating, 229 reviews

A log cabin with a green metal roof features a stone fireplace and a welcoming front porch. The cabin is surrounded by trees, providing a sense of seclusion. The porch extends out to the front, offering space for outdoor seating.

Guesthouse in Dobson

The Cottage at Haze Gray Vineyards

LocationFamilyGetting around

4.9 out of 5 average rating, 62 reviews

The spacious studio layout features a queen bed with light-colored bedding, complemented by a decorative throw. A small dining table and chairs are seen to one side, with a trunk serving as additional storage at the foot of the bed. Natural light enters through multiple windows, dressed with sheer curtains.

Guesthouse in High Point

Hillcrest Hideaway

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4.67 out of 5 average rating, 3 reviews

Dandelion Guesthouse - Relaxing Getaway

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Guesthouse in Kernersville

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.

4.95 out of 5 average rating, 133 reviews

The Bungalow at Weather Ridge

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4.8 out of 5 average rating, 163 reviews

Guesthouse in High Point

Carolina Cottage

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Guesthouse in Downtown Greensboro

A spacious studio apartment features a queen-sized bed with bright floral bedding. There is a comfortable armchair beside a small round table. A decorative plant adds a touch of nature, while large windows allow natural light to fill the space.

4.98 out of 5 average rating, 482 reviews

Gate City Studio - Downtown Greensboro

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A spacious bed with a wooden headboard sits against a yellow wall, featuring a multicolored quilt spread across the top. Two soft pillows are arranged at the head of the bed. A small bookshelf is positioned nearby, containing books and a lamp.

Guesthouse in Winston-Salem

4.61 out of 5 average rating, 28 reviews

Rustic Urban Sanctuary

LocationFamilyOutdoor spaces

4.97 out of 5 average rating, 37 reviews

A gentle cow is seen standing in a green pasture, surrounded by wildflowers. A rustic barn is visible in the background, with rolling hills and trees extending into the distance. The sky is partly cloudy, glowing with warm sunset tones.

Guesthouse in Lexington

Sunset Hill Pastures

ValueFamilyQuiet

Guest house rentals with a patio

A spacious bed is covered with a textured coral duvet, complemented by two patterned pillows and an accent pillow. Large windows provide ample natural light, framed by soft curtains. A floor lamp stands nearby, adding warmth to the inviting sleeping area.

4.99 out of 5 average rating, 118 reviews

Hamilton Loft (Modern and Near the Lake!)

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5.0 out of 5 average rating, 37 reviews

The spacious living area features natural wood paneling and a sloped ceiling. A large TV is mounted on the wall opposite a comfortable sofa, with a fluffy ottoman nearby. A colorful gameboard adds a playful touch.

Guesthouse in Advance

The Bunkhouse at Olde Stone Farm

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4.9 out of 5 average rating, 40 reviews

Guesthouse in Jamestown

The cozy duplex

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A living area is seen featuring a leather couch positioned near a front door with a glass panel. Above, several small windows allow natural light to illuminate the space. Framed photographs are displayed on the wall beside the couch, enhancing the room's decor.

5.0 out of 5 average rating, 60 reviews

The Stratford Guesthouse

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4.68 out of 5 average rating, 37 reviews

Guesthouse in Jamestown

Comfort duplex

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5.0 out of 5 average rating, 11 reviews

Elm Street Cottage

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Guesthouse in Winston-Salem

4.83 out of 5 average rating, 6 reviews

Renovated+ Safe + Private

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4.96 out of 5 average rating, 141 reviews

The hot tub is nestled under a canopy of string lights, creating a warm ambiance at night. Two guests are seated inside, relaxing as the gentle lights illuminate the surrounding area. A view of the guesthouse is visible in the background.

Guesthouse in Walkertown

Cozy Cottage with Hot Tub

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Guest house rentals with a washer and dryer

A spacious living room is furnished with a dark sectional sofa and a green accent chair. A wooden coffee table centers the space, surrounded by a patterned rug. Bright artwork featuring a cow hangs on the wall, with a window providing natural light.

4.93 out of 5 average rating, 212 reviews

The Bright Spot - Walk to Downtown Greensboro

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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.

4.97 out of 5 average rating, 444 reviews

Stylish Hamilton Lakes Studio Facing Park/Trails

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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.

4.95 out of 5 average rating, 190 reviews

Leafy, Suburban Abode

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5.0 out of 5 average rating, 32 reviews

A cozy entrance to the apartment is highlighted by soft pathway lights, illuminating the stone walkway leading to the stairs. The exterior of the building is adorned with a wooden deck above, surrounded by lush trees, providing a serene, natural ambiance.

Guesthouse in Lexington

The Fiddling Frog Guest House

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Guesthouse in Kernersville

A cozy studio space is presented, featuring a comfortable gray sofa and a round coffee table atop a patterned rug. A bright orange bed is illuminated by natural light. Storage cabinets are positioned nearby, while diverse wall art adds character to the walls.

5.0 out of 5 average rating, 73 reviews

Rapunzel’s Hippie Inn

ValueFamilySleep quality

Guesthouse in Winston-Salem

A spacious studio layout includes a cozy seating area with a large sofa and decorative pillows. A comfortable bed is positioned against the wall, complemented by a wall clock and artwork. Natural light enters through two windows, enhancing the calming blue walls.

4.75 out of 5 average rating, 52 reviews

Golden Studio, few minutes to Downtown.

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4.82 out of 5 average rating, 17 reviews

Guesthouse in Clemmons

Guest House at Tall Tree Manor

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A modern kitchen featuring stainless steel appliances, including a refrigerator, microwave, and oven. A black granite island with two woven barstools offers a casual dining space. White cabinetry and tile backsplash create a bright, clean atmosphere, enhanced by natural light from the nearby window.