Guest house 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, 232 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, 243 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.

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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, 178 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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Guest house 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.

LocationFamilyTV

4.96 out of 5 average rating, 303 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.

Guest house 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.

FamilyValueOutdoor spaces

4.99 out of 5 average rating, 101 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.

Guest house 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.

ValueFamilyBack garden

4.93 out of 5 average rating, 282 reviews

A bright kitchen space is equipped with white cabinetry and granite countertops. Stainless steel appliances are included, along with a coffee machine. A small dining area with bar stools is positioned next to a window, providing natural light to the room.

Guest house in Jamestown

Peaceful 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.

ValueFamilyAir conditioning

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, 103 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.

ValueFamilyHospitality

4.96 out of 5 average rating, 551 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.

Guest house 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, 1,351 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.

LocationValueLayout

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, 504 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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Guest house in Mocksville

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.

4.97 out of 5 average rating, 140 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!

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Popular amenities for guest house rentals in Winston-Salem

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guest house in High Point

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.

5 out of 5 average rating, 36 reviews

The Little White House

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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.

4.61 out of 5 average rating, 28 reviews

Rustic Urban Sanctuary

LocationFamilyHospitality

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

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4.86 out of 5 average rating, 293 reviews

The Friendly Place

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Guest house in High Point

4.8 out of 5 average rating, 163 reviews

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

LocationQuietKitchen

Superhost

4.67 out of 5 average rating, 3 reviews

Dandelion Guesthouse - Relaxing Getaway

LocationCheck-inComfort

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.

Guest house in King

Ooh La La Serene Private Basement Apt!

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Guest house rentals 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, 188 reviews

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

ValueLocationShared spaces

Guest house in Mocksville

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.

4.99 out of 5 average rating, 165 reviews

Entire Private Entrance Studio Apartment with Pool

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Superhost

4.83 out of 5 average rating, 6 reviews

Renovated+ Safe + Private

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5 out of 5 average rating, 9 reviews

Elm Street Cottage

LocationComfortView

5 out of 5 average rating, 35 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.

Guest house in Advance

The Bunkhouse at Olde Stone Farm

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4.93 out of 5 average rating, 29 reviews

Guest house in Jamestown

The cozy duplex

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Guest house in Walkertown

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.

4.96 out of 5 average rating, 141 reviews

Cozy Cottage with Hot Tub

ValueFamilyCondition

5 out of 5 average rating, 7 reviews

Guest house in Ardmore

Secret Garden cottage on Queen St.

LocationCheck-inParking

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.

4.78 out of 5 average rating, 51 reviews

Golden Studio, few minutes to Downtown.

ValueLocationCleanliness

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

LocationFamilyAir conditioning

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, 209 reviews

The Bright Spot - Walk to Downtown Greensboro

FamilyValueView

5 out of 5 average rating, 28 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.

Guest house in Lexington

The Fiddling Frog Guest House

LocationFamilyComfort

4.81 out of 5 average rating, 16 reviews

Guest house in Clemmons

Guest House at Tall Tree Manor

ValueFamilyCleanliness

Guest house 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, 12 reviews

Pickleball and Privacy

LocationFamilyComfort

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, 443 reviews

Stylish Hamilton Lakes Studio Facing Park/Trails

ValueFamilyBathroom

A spacious living area features new LVP flooring and a cozy grey sofa. Light streams through large windows covered by deep blue curtains. A round dining table is positioned nearby, while decorative elements, including a patterned rug and accent chairs, enhance the inviting space.