Guesthouse holiday 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 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.

4.98 out of 5 average rating, 247 reviews

Gate House Garden

Walk down the path to your mini suite: a cozy studio with an open floor plan, kitchenette (microwave & toaster over), walk-in shower, queen bed, & private deck. Great for 2 guests or a place to work remotely. 5-min walk to scenic lake/trails. We are in a very quiet neighborhood, so 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 min to High point.

ValueLocationGetting around

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.

ValueFamilyCleanliness

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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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.

LocationFamilyCleanliness

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.

FamilyValueWalkability

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.

ValueFamilyHeating

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.

ValueFamilyWi-Fi

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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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, 508 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 guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

5 out of 5 average rating, 36 reviews

A contemporary living area is displayed, featuring a brown leather sofa with throw pillows and an armchair. A wooden coffee table is positioned in front, and a desk with a chair is located against the wall. Natural light streams through the windows, highlighting the green plant nearby.

Guesthouse in High Point

The Little White House

LocationFamilyLong stay

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.

4.61 out of 5 average rating, 28 reviews

Rustic Urban Sanctuary

LocationFamilyWalkability

The exterior of a guest home is surrounded by tall trees, with sunlight filtering through the leaves. A gravel driveway leads to the entrance, which features several large windows and a combination of brick and neutral siding. The peaceful setting emphasizes a connection with nature.

5 out of 5 average rating, 6 reviews

Adorable cottage surrounded by nature

LocationFamilyAmenities

4.8 out of 5 average rating, 163 reviews

Guesthouse in High Point

Carolina Cottage

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The kitchen area features wooden cabinetry with a warm finish, complemented by a large window that allows natural light. Countertops provide workspace, and appliances are visible, including a microwave and coffee maker. The floor is comprised of wood-like laminate for easy upkeep.

4.75 out of 5 average rating, 4 reviews

Moon Roosters

LocationAir conditioningIndoor spaces

Superhost

4.67 out of 5 average rating, 3 reviews

Dandelion Guesthouse - Relaxing Getaway

LocationHospitalityComfort

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

FamilyLocationLong stay

5 out of 5 average rating, 7 reviews

The charming retreat is showcased with a blend of brick and siding, featuring a welcoming front porch and a distinct metal roof. Lush green grass surrounds the home, and colorful flower beds add visual interest, all under a bright blue sky with fluffy clouds.

Guesthouse in King

Ooh La La Serene Private Basement Apt!

LocationFamilyAccuracy

Guesthouses with a patio

A well-lit bedroom includes a spacious bed adorned with a navy blue blanket. A 65-inch Samsung Smart TV is mounted on the wall, and a crib is positioned nearby. A small desk and chair provide a designated workspace, adding to the suite's functionality.

4.71 out of 5 average rating, 190 reviews

3 mins to Uptown - Early Check-in, PS5, EV Charger

FamilyLocationWi-Fi

4.99 out of 5 average rating, 170 reviews

A clear blue swimming pool is framed by a brick border, featuring a small rock fountain. Red umbrellas provide shade over black patio tables and chairs arranged nearby, with well-maintained landscaping surrounding the area. The back of a light-colored house is visible in the background.

Guesthouse in Mocksville

Entire Private Entrance Studio Apartment with Pool

ValueFamilyPets

Superhost

4.83 out of 5 average rating, 6 reviews

Renovated+ Safe + Private

LocationValueCleanliness

5 out of 5 average rating, 11 reviews

Elm Street Cottage

FamilyLocationDecor

5 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

LocationFamilySleep quality

4.9 out of 5 average rating, 40 reviews

Guesthouse in Jamestown

The cozy duplex

ValueLocationHospitality

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

FamilyValueQuiet

5 out of 5 average rating, 7 reviews

Guesthouse in Ardmore

Secret Garden cottage on Queen St.

LocationQuietHospitality

Guest house rentals with a washing machine and dryer

Superhost

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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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

ValueFamilyBarbecue

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

FamilyLocationView

5 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

ValueFamilyComfort

4.82 out of 5 average rating, 17 reviews

Guesthouse in Clemmons

Guest House at Tall Tree Manor

LocationValueAccuracy

Guesthouse in Summerfield

The exterior of a two-car garage is shown, featuring a mix of light gray siding and brick. A private entrance with a white door is visible on the left side, framed by a well-maintained driveway and grassy area, with clouds in the bright blue sky above.

5 out of 5 average rating, 15 reviews

Pickleball and Privacy

LocationFamilySolo travel

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

ValueLocationBiking