Vacation rentals in Winston-Salem

4.99 out of 5 average rating, 178 reviews

The Zen Ranch - Spacious Layout with Modern Decor

1960s ranch style home on 2 acres with 2,400ft² interior. This home has been fully remodeled with a large open floor plan and all modern amenities and decor. With ample yard and patio space, large bedrooms, bonus room and 3 full bathrooms there is plenty of space to spread out. • Abundant Natural Lighting • Backyard w/ patio + fire pit + hammocks • Comfy Beds • Fully stocked Chefs Kitchen • Large Private Deck + BBQ grill • Indoor fireplace • 400Mps WiFi • 3 x 4K TVs w/ Disney, Netflix & Prime

Apartment in Winston-Salem

4.97 out of 5 average rating, 116 reviews

K-Obscura, Romantic Downtown loft

Historic loft in Downtown Winston Salem's Innovation Quarter. Located above Krankies Coffee near WFB Medical School and Bailey Park.Short walking distance to several restaurants and bars. This space has private entrance and patio. Includes complimentary coffee and treat at Krankies. Quiet for a downtown spot with the exception of an occasional train passing through adjacent lot. Includes deep soaking tub, mini-kitchen and comfy king size bed. Space is accessed via stairs. Parking included.

Guest suite in Winston-Salem

A cozy entertainment space features a pool table and a large TV against a back wall. A comfortable couch is situated in front, with various music-themed decorations adorning the ceiling. Natural light filters in through a window, enhancing the inviting atmosphere.

4.99 out of 5 average rating, 578 reviews

The Man Cave

The Man Cave is close to the highway. It is minutes away from downtown Winston-Salem, Wake Forest University, Hanes Mall, and Baptist Hospital. You'll love the place because of its private entrance and great "Man Cave" amenities... King bed, wi-fi, pool table, dartboard, 50" TV & DirecTV satellite cable, Keurig machine, full kitchen, washer/dryer, etc. Don't let the name fool you... It is good for a couples get away, solo adventurers, and business travelers looking for a unique experience.

Guest suite in Winston-Salem

4.99 out of 5 average rating, 282 reviews

Private, Peaceful, Green Hideaway 6 Minutes to WFU

Just minutes from Wake Forest, we have a completely remodeled this very special place. We have often stood at the huge windows of this ground level space and watched mother deer with their fawns play in the yard. Your home away from home is at the end of an already quiet cul-de-sac so traffic noise is zero. Your suite is completely private with its own ground level entrance. Your kitchen has a full size sink, an induction stove, fridge, with all your cookware, dishes. New bath with tub.

Guest suite in Winston-Salem

4.95 out of 5 average rating, 136 reviews

Entire COZY Unit - 3 min walk to WFU.

Welcome to your cozy - little net. Please keep in mind that this unit is attached to our house (we shared a wall - different entrance). Everything showed in the pictures will be all yours (Master bedroom, Study room - living room Space, and an extraordinary bathroom). When staying at our place, you are: - 3 min drive (10min walk) to WFU Campus. - 5 min drive to Downtown. - 3 min WALK to Stadiums and Restaurants. - 10min drive to Wake Forest Baptist Hospital. - Reynolda House museum.

4.98 out of 5 average rating, 106 reviews

Elegant Pet Friendly Ranch close to everything!

Our sun filled updated 1950's single family ranch home in a quiet and beautiful neighborhood has all the comforts needed for a long or short stay. Fabulous location-just minutes to multiple universities, hospitals, historic sites and downtown Winston-Salem. Nearby are plenty of restaurants, shopping and recreational parks. Piedmont Triad Airport in Greensboro is 35 minutes away. ***ALLERGY ALERT*** I do have the house professionally cleaned but dogs and cats do stay here occasionally.

4.89 out of 5 average rating, 833 reviews

A wooden countertop showcases a smooth, glossy surface with natural grain patterns. The rich brown tones are contrasted by a lighter border, highlighting the craftsmanship. Warm lighting reflects off the polished finish, creating a warm and inviting workspace in the kitchen area.

Cabin in Ardmore

Log Cabin in the city, w/Brewery Tour and Tasting

READ ENTIRE LISTING! NO PARTIES/ GATHERINGS. Only the guests on the reservation are allowed to be on my property. I WILL KICK YOU OUT AND CALL THE COPS. I DO NOT PLAY GAMES. The listing is the entire UPPER LEVEL of my log cabin, which is conveniently located less than a mile from Downtown Winston-Salem! The back yard is surrounded by woods and a privacy fence with a hammock and fire pit that is available to use! Great place close to downtown. NO SMOKING of any kind allowed anywhere.

4.97 out of 5 average rating, 156 reviews

Condo in Winston-Salem

Old Salem Getaway - Visit DTWS via the Strollway

We love our comfy third floor condo with elevator access. Whether you are in town for business or pleasure, this condo fits the bill. Walk to Old Salem, UNCSA, and Salem College. Jog or bike Salem Creek trail, which is at our doorstep. Stroll through Old Salem on your way to downtown’s amazing eateries and breweries. Close by are Wake Forest University, WSSU and downtown Winston-Salem, and hospitals - this condo is central to anywhere in the Winston-Salem area.

4.96 out of 5 average rating, 481 reviews

A hammock is positioned comfortably on a grassy area, surrounded by lush greenery. Sunlight filters through the trees, creating a serene atmosphere. Nearby, a covered picnic shelter is partially visible, featuring seating for relaxation.

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.

4.97 out of 5 average rating, 564 reviews

A spacious bedroom features a wooden bed with a gray quilt and decorative pillows. Two bedside tables with lamps flank the bed, and a window allows natural light to fill the room. A framed picture adorns the wall above the bed.

Home in Ardmore

Camel City Cottage - located near the hospitals

Our *non-smoking* home is located in the desirable Ardmore residential area of Winston-Salem...quiet yet still close to many restaurants and shopping. This cottage has all the modern amenities while still retaining it's 1940's cottage charm. The kitchen has been completely remodeled and has all the appliances you would need. The living room and each bedroom have a TV with an antennae and access to your streaming services such as Roku, Prime, and Sling.

4.94 out of 5 average rating, 364 reviews

Condo in Winston-Salem

A Bright Spot in West End

Welcome to the Shenandoah house condominiums! Located in the historic West End neighborhood of downtown Winston-Salem. Spacious one bedroom with lots of natural light, hardwood floors, eat in kitchen and private screened porch. Filled with works from many of Winston's local artists. Fully equipped for your stay. Easy walking distance to restaurants, bars, shopping, entertainment, breweries, parks and public transportation. Free parking!

Apartment in Winston-Salem

4.96 out of 5 average rating, 276 reviews

West Salem Art Hotel, "Art"partment #1

Welcome to the West Salem Art Hotel! This eclectic and beautiful apartment is located in a 1931 historic brick building only 1 mile from Downtown Winston-Salem! All the conveniences of staying JUST on the outskirts in Historic West Salem, without all the city noise, AND located in the middle of a peaceful urban garden! We are minutes away from the best eateries/entertainment W-S offers! Private, unique, and clean.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Winston-Salem vacation rentals

Self check-in

Pet friendly

Hot tub

Laptop-friendly workspace

Monthly stays

Stay near Winston-Salem's top sights

Reynolda House Museum of American Art42 locals recommend

Benton Convention Center7 locals recommend

Village Tavern6 locals recommend

Whole Foods Market10 locals recommend

Mozelle's Fresh Southern Bistro40 locals recommend

Foothills Brewpub22 locals recommend

Pet-friendly vacation rentals in Winston-Salem

4.91 out of 5 average rating, 116 reviews

A single-story home is framed by tall trees, with a welcoming front porch featuring a wooden railing. The exterior showcases a blend of neutral siding and brick at the base, while large windows are dressed in burgundy shutters. A grassy area surrounds the house.

Home in Walnut Cove

Modern and Spacious cottage, centrally located

4.91 out of 5 average rating, 165 reviews

A wooden dock extends across calm waters, leading toward a small island surrounded by trees. Clear blue skies reflect on the water's surface, and a grassy area with stones borders the shoreline. Two trees provide shade near the dock.

Home in Lexington

Lakefront Getaway with Private Dock – 2BR Retreat

4.97 out of 5 average rating, 115 reviews

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

“Home” on the Road!

4.98 out of 5 average rating, 123 reviews

The cozy blue bungalow features a welcoming front deck with wooden railings. Large windows allow natural light to fill the interior. The surrounding yard is grassy, with scattered trees in the background and a clear sky above, providing a serene outdoor environment.

Home in Jonesville

Little Blue Bungalow

4.94 out of 5 average rating, 271 reviews

The log cabin features a green metal roof and a stone chimney. A welcoming porch is supported by wooden beams and lined with flower baskets. Lush green grass surrounds the structure, complemented by trees in the background, creating a serene outdoor setting.

Cabin in Summerfield

Cozy chic log cabin overlooking horse pastures

4.95 out of 5 average rating, 125 reviews

A modern kitchen features white cabinetry and a large island with seating for three. Stainless steel appliances and a stylish backsplash enhance the functional layout. Natural light fills the space through a window, highlighting the sleek countertops and inviting atmosphere.

Home in Greensboro

The Bent Oak Retreat

4.81 out of 5 average rating, 152 reviews

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

Private cottage, pet-friendly

4.93 out of 5 average rating, 520 reviews

A rustic two-story cabin with wood siding and a corrugated metal roof is nestled among trees. The front features two windows on the upper floor, with a porch area that includes a railing, creating a welcoming outdoor space.

Cabin in Asheboro

Peach's Paradise Eco-Cabin & Bath In The City!

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House rentals in Winston-Salem

4.94 out of 5 average rating, 109 reviews

A dining area is presented featuring a long wooden table set for a meal, with plates, glasses, and greenery accents. Four high-backed chairs with leather seats complement the table. Natural light filters in through nearby windows adorned with sheer curtains, illuminating the space.

Home in Greensboro

CasaLuna: Graduation & Summer ready in GSO!

Home in Downtown Greensboro

The exterior of a two-story house is visible, featuring a large front porch with two white rocking chairs. A manicured lawn and beige siding add to its appearance. A concrete pathway leads to the front door, framed by neatly finished landscaping.

4.92 out of 5 average rating, 25 reviews

Big House Downtown! 6BR 3BTH!

A cozy bedroom is highlighted by a spacious bed adorned with layered bedding and decorative cushions. Soft, natural light enters through two windows dressed with lush green curtains, complementing the botanical-patterned wallpaper. Nightstands flank the bed, each topped with a lamp.

5 out of 5 average rating, 20 reviews

Premium Retreat close to WFU w/ Lvl 2 EV Charger

Superhost

A comfortable living space is presented, featuring a light-colored coffee table at the center. A blue armchair and a gray sofa offer seating options. Two mirrors are positioned across from the doorway, while a television is mounted on a stand against the wall.

Home in Kernersville

4.81 out of 5 average rating, 120 reviews

Quaint 2 bed 1 bath cottage style home

A cozy living area features a comfortable sectional sofa adorned with decorative cushions. A wooden coffee table rests in the center, complemented by a small potted plant. Natural light enhances the space, filtering through sheer curtains alongside darker drapes.

4.85 out of 5 average rating, 119 reviews

Little house by the Coliseum

4.92 out of 5 average rating, 249 reviews

The charming farmhouse presents a welcoming facade with classic architectural details. A large porch is adorned with white railings, while a pathway leads through a grassy area. The home is surrounded by trees and features a light-colored exterior complemented by decorative trim.

Home in Mayodan

Home away from home.. 20 minutes-Greensboro/Triad

4.96 out of 5 average rating, 102 reviews

A serene view of the landscape is displayed, featuring two bare trees flanking either side. A vast lawn stretches toward the horizon, where the sun sets, casting a warm glow across the sky and illuminating the clouds.

Home in Belews Creek

Deer Hill - 1450 sq. ft. of Comfort & Convenience

Superhost

A dining area is highlighted by a modern glass table surrounded by black chairs. Elegant red curtains frame the windows, and a piece of wall art featuring a vase and flowers complements the decor. A large refrigerator is positioned beside the table.

4.83 out of 5 average rating, 65 reviews

3 bedrooms close to downtown, Hospital & college

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Vacation rentals with jacuzzis in Winston-Salem

4.9 out of 5 average rating, 204 reviews

A serene lakeside view is captured during sunset, showcasing vibrant hues of pink and orange in the sky. Silhouetted trees line the shore, while a private dock extends into the water, offering a tranquil spot for relaxation amidst nature.

Cottage in Lexington

Peaceful high rock lake front cottage !

Superhost

A private outdoor space features a round stock tank pool surrounded by a pebbled area. Two colorful inflatable pool toys rest in the water. Comfortable seating arrangements with woven chairs are paired with hammocks, creating a cozy atmosphere amidst lush greenery.

4.89 out of 5 average rating, 282 reviews

Cozy King Blue H2O Staycation , Pool & Hot Tub

4.9 out of 5 average rating, 176 reviews

A charming private home is set within a spacious green yard, surrounded by mature trees. A brick chimney rises from the roof, while a pathway leads to the entrance, creating a welcoming entry. The tranquil atmosphere of the outdoors is enhanced by the natural surroundings.

Home in Summerfield

Private. Hot Tub & Movie Den. 7 mins to Airport

4.98 out of 5 average rating, 138 reviews

A workout room is shown, featuring a wooden sauna with glass doors and a treadmill positioned beside it. Fresh towels are stacked on a shelf nearby, and large windows allow natural light to fill the space, complemented by neutral-colored walls.

Home in Greensboro

Relax at Beck & Call Sauna, Hot tub, mini-Gym

4.98 out of 5 average rating, 125 reviews

The log cabin treehouse stands elevated, illuminated by warm string lights. Sturdy wooden stairs lead up to the entrance, while gravel surrounds the base. Large windows reflect the inviting glow from within, creating a cozy outdoor ambiance.

Treehouse in Dobson

Whip-O-Will Cabin: Secluded Log Cabin Treehouse

4.99 out of 5 average rating, 128 reviews

An open living area features a stone fireplace as the focal point, surrounded by large windows that allow natural light to illuminate the wooden walls and ceiling. A cozy seating arrangement, including a dark sofa and coffee table, complements the cabin's rustic charm.

Cabin in Lewisville

Cozy renovated 3 bedroom cabin with hot tub

4.9 out of 5 average rating, 173 reviews

A vibrant courtyard features a cozy guest cottage with a red roof and colorful outdoor accents. Lounge chairs sit among green foliage, while a patterned tapestry hangs nearby. Bright umbrellas provide shade, creating an inviting outdoor space surrounded by a rustic wooden fence.

Farm stay in Ararat

Farm Studio w/hot tub & fenced yard