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, 230 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.

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, 241 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.

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, 174 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.

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, 110 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.

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

Ready for a romantic weekend getaway? Or just a break to get away to the country? This beautiful log cabin situated in a vineyard in the heart of the Yadkin Valley wine country. Our tasting room is situated on the other side of the vineyard where you can taste our wines made from the grapes we grow in our own vineyard. We are located close to several wineries in the local area. Other local Attractions include Rockford General Store, Pilot Mountain. Mt Airy or hiking at numerous parks.

4.96 out of 5 average rating, 299 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.

Guesthouse in Statesville

A wooden sign displaying 'Blackberry Hills Farm' is mounted on a fence post. The sign features a rustic design with a distressed finish. Behind, a vast green field stretches out, dotted with bales of hay and framed by trees on the horizon.

4.98 out of 5 average rating, 123 reviews

The Old Welding Shop

Relax with the whole family at this peaceful setting. Close to interstate 77 and 40, this rural farm is rustic elegance. With a library for the family and a vintage-inspired home theater with classic DVD's, you have plenty to do even on rainy days. The bedroom has a king bed, and the main room includes a trundle with two twins and a futon sofa. This 900 sq. ft. guesthouse was the old welding shop from years ago and gives you access to walking trails and the farm burn pit.

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.

4.96 out of 5 average rating, 544 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.

4.99 out of 5 average rating, 392 reviews

A two-story wooden house is surrounded by greenery, with a driveway leading up to the entrance. A deck is visible on the left side, offering a vantage point of the landscape. The entrance features a staircase leading up to the main level.

Guesthouse in Lexington

Mountain View Retreat

The Mountain View Retreat is the perfect place for those who want to enjoy a combination of luxury and the rustic outdoors. Located on 63 acres near Lexington and Thomasville, the Retreat is an easy drive from many of the major cities in central North Carolina. An ideal spot for couples or solo travelers looking for a place to relax, unwind, enjoy nature, and have a weekend away in the country. 20% weekly/30% monthly discounts.

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, 1,347 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.

4.92 out of 5 average rating, 333 reviews

A modern kitchen features light gray cabinets and sleek countertops. Four bar stools are positioned at a central island. Appliances include a refrigerator, oven, and coffee maker. Natural light fills the space through a nearby window, while decorative plants add a touch of greenery.

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, and both Downtown Greensboro and High Point. Downtown Jamestown is only 5 minutes away.

Popular amenities for Winston-Salem guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

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.

4.58 out of 5 average rating, 26 reviews

Rustic Urban Sanctuary

4.98 out of 5 average rating, 154 reviews

A well-furnished room features a plush sofa, club chair, and a queen bed, all accentuated by natural light from large windows. Wooden floors add warmth, and a ceiling fan provides comfort. A television is mounted on the wall, complemented by a dresser and decorative items.

Guesthouse in Lexington

Marwood Cottage on the lake

A cozy sleeping area features a spacious bed covered with a blue quilt. Striped pillows add a touch of color. A decorative lamp stands beside the bed, illuminating the space. A small table and coffee maker are positioned near the room's entrance, with an adjoining bathroom visible.

4.77 out of 5 average rating, 114 reviews

Guest Quarters

4.79 out of 5 average rating, 160 reviews

Guesthouse in High Point

Carolina Cottage

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

Superhost

4.84 out of 5 average rating, 107 reviews

Dandelion Guesthouse - Relaxing Getaway

A small cabin guesthouse is framed by lush greenery, showcasing its white exterior and a welcoming front window. Soft sunlight filters through the leaves, creating a serene ambiance around the private entrance and patio area.

Guesthouse in High Point

Farmhouse Guesthouse

5 out of 5 average rating, 6 reviews

Guesthouse in Ardmore

Secret Garden cottage on Queen St.

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.

4.74 out of 5 average rating, 185 reviews

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

4.99 out of 5 average rating, 157 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

5 out of 5 average rating, 6 reviews

Elm Street Cottage

5 out of 5 average rating, 34 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

Guesthouse in Mocksville

5 out of 5 average rating, 3 reviews

Cozy Guesthouse w/ Pool

5 out of 5 average rating, 33 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

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

5 out of 5 average rating, 54 reviews

A spacious bedroom features a comfortable bed with a light gray blanket and decorative pillows. Two windows allow natural light, while indoor plants and decorative items add a touch of nature. A ceiling fan provides airflow, and wooden furnishings provide a warm contrast.

Guesthouse in Ardmore

Melrose Place

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, 50 reviews

Golden Studio, few minutes to Downtown.

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

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, 207 reviews

The Bright Spot - Walk to Downtown Greensboro

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

5 out of 5 average rating, 26 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

4.79 out of 5 average rating, 14 reviews

Guesthouse in Clemmons

Guest House at Tall Tree Manor

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, 9 reviews

Pickleball and Privacy

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.