We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Vacation rentals in Winston-Salem

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winston-Salem

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

The charming exterior of a single-story home is presented, featuring a bright red front door. Flanking the entrance are two symmetrical windows, while landscaped bushes and a path lead to the porch. A tree provides shade, enhancing the welcoming appearance.

Home in West Salem

4.95 out of 5 average rating, 127 reviews

The Walnut Cottage. Charming! Near Everything!

Relax in the historic West Salem district. Central to UNCSA, WSSU, WFU, Carolina University, hospitals, downtown, dining, shopping, parks/greenways and 18th century town of Old Salem. Enjoy cozy seating areas, or head out to the patio, relax on the screened porch or grill on the deck. Off street parking, WiFi, smart TVs in each room, updated kitchen with gas range. 2nd living room in mini suite with workspace and Ethernet port. Beds: 2 queens, 1 full and 1 futon. Keyless entry. Washer/Dryer

Top guest favorite

A recreational area features a spacious pool table centered beneath three pendant lights. Surrounding walls display various signs and memorabilia, including a dartboard. Two high-backed chairs are positioned at the side, and natural light filters in through a window with closed blinds.

Guest suite in Winston-Salem

4.98 out of 5 average rating, 601 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.

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.

Home in Winston-Salem

4.89 out of 5 average rating, 299 reviews

Cozy King Blue H2O Staycation , Pool & Hot Tub

Quiet secluded STAYCATION w/ Fully Fenced Back Yard for the PUPS. We have a hot tub for year round use and a Stock Tank Pool (Closed until 5/23/25) . A fire pit to unwind. Back yard BBQ with a built in bar top table and a cozy Sectional to enjoy the outdoors. Inside we have an amazing plush King size mattress to take all stress away. Full kitchen * Hot tub - I will do my best to have it available at all times unless there is a mechanical issue. (No refunds if hot tub is not available)

Top guest favorite

A spacious suite features a large bed with decorative pillows and a patterned throw. A dresser and chair are positioned near a window, allowing natural light to fill the area. A television and a small table are present, along with a comfortable seating arrangement.

Guest suite in Winston-Salem

4.99 out of 5 average rating, 292 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.

A charming cottage is nestled among lush greenery. The exterior features a peaked roof and decorative shutters, while a small porch greets visitors. Vibrant foliage frames the entrance, creating a welcoming ambiance in this tranquil residential setting.

Home in Winston-Salem

4.97 out of 5 average rating, 176 reviews

Salem Twin Deck

Conveniently located in downtown Winston-Salem, this well-maintained cottage built in 1900 includes a recently updated kitchen with island, wood floors, dining room, living room with full futon, washer/dryer, bedroom with queen, beautiful bathroom and walk-in shower. Easy walking distance to downtown restaurants, short drive to WFU main campus, Med School, WSSU and UNCSA. One off-street parking spot available. Self check-in only, but we live next door if you need anything or have questions.

A vibrant outdoor space features several tables and umbrellas in blue, pink, and red shades. Green vines cascade from the second-floor balcony, complemented by a large red umbrella, creating a refreshing atmosphere. The textured white wall serves as a backdrop for this inviting area.

Apartment in Winston-Salem

4.95 out of 5 average rating, 134 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 gift card for coffee at Krankies. Note there is a train that passes by a few times a day and at night. We do allow pets but have a fee. Includes deep soaking tub, mini-kitchen and comfy king-size bed. Space is accessed via stairs. Parking included.

Top guest favorite

A spacious bathroom features a large jetted tub set against bay windows, providing natural light. Dual sinks are positioned on a granite countertop, while a potted plant adds a touch of greenery. Black and white patterned flooring contrasts with the light-colored walls.

Guest suite in Winston-Salem

4.95 out of 5 average rating, 157 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.

Top guest favorite

A single-family ranch home is showcased with a stone accent exterior, surrounded by well-maintained landscaping. A paved driveway leads to the entrance, while trees and flowering plants add natural beauty to the front yard.

Home in Winston-Salem

4.98 out of 5 average rating, 112 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.

Top guest favorite

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

4.96 out of 5 average rating, 497 reviews

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.

A cozy bedroom is presented, featuring a spacious bed adorned with a rust-colored quilt. A decorative lamp casts light beside a dark wood nightstand, accentuated by sculptural art pieces on display. A soft texture of a woven rug completes the inviting atmosphere.

Apartment in Winston-Salem

4.95 out of 5 average rating, 288 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.

A single-family home features a light-colored exterior with blue shutters. A large, attached garage is visible, with a paved driveway leading to it. The front yard is well-maintained, showcasing shrubs and a tree with vibrant autumn foliage.

Home in Winston-Salem

4.92 out of 5 average rating, 190 reviews

"Deacon House" 3 bedrooms

Looking for a place to stay in Winston Salem? Check out this 1,315 sqft. single family home that has 3 bedroom and 2 full bath. It has its own driveway with 2 car garage attached and fenced in backyard, guest occupy the entire house except the attic. It is just a few minutes away from downtown, Wake Forest University, Reynolda Garden, LJVM coliseum, Starbucks and grocery stores.

The living room features hardwood floors and light green walls, providing a bright and airy feel. A leather couch faces a coffee table, while a small TV is positioned on a wooden stand. Natural light enters through a window beside the front door.

Apartment in Winston-Salem

4.93 out of 5 average rating, 620 reviews

Urban oasis in downtown W-S; sparkling clean

Top unit of a three-family house, this 1000 sq ft. 2 bedroom, 1 bath apartment is in the heart of downtown Winston-Salem. Please review our house rules before you book. It is an ideal location two blocks away from all of the action of Fourth and Trade Streets, tucked into a funky, tree-lined neighborhood that is quiet and private.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Winston-Salem vacation rentals

Laptop-friendly workspace

Winston-Salem house rentals

Top guest favorite

A dining area is highlighted by a wooden table surrounded by four upholstered chairs. An open-concept layout leads to a stylish living area featuring a patterned rug, a cozy seating arrangement, and artwork accentuating the walls, all illuminated by overhead lighting.

Home in Ardmore

4.96 out of 5 average rating, 125 reviews

Contemporary Cottage Gem | 4 mins Bapt Hospital

The cozy bedroom features a spacious bed with a white comforter and decorative pillows. Two windows allow natural light to brighten the space. A small lamp and nightstand provide essential bedside furnishings, complemented by a colorful area rug underfoot.

Home in Winston-Salem

4.91 out of 5 average rating, 133 reviews

The Morning Star Lofts

A charming home is set within a tranquil landscape, featuring a well-maintained exterior with dark gray siding and white trim. The front door is painted bright teal, framed by black shutters. A brick chimney and landscaped garden enhance the inviting appearance of the property.

Home in Winston-Salem

4.84 out of 5 average rating, 133 reviews

Camilas House

The main bedroom features a sizable bed with a dark gray throw and neatly arranged towels. Two bedside lamps provide soft illumination beside the bed. The room is complemented by two framed artworks, and a bathroom with glass door access is visible in the background.

Home in Winston-Salem

4.96 out of 5 average rating, 184 reviews

Beautiful 2 BR home with Office and Game Room

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

4.96 out of 5 average rating, 104 reviews

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

An open living space is showcased, featuring a comfortable sofa and a decorative coffee table atop an area rug. Elegant pendant lights hang above a dining area with a rectangular table. A kitchen with modern appliances and a countertop is visible in the background.

Home in Winston-Salem

4.89 out of 5 average rating, 18 reviews

Cozy spacious townhome!

A red brick home is set within a spacious yard, surrounded by lush greenery and blooming flowers. Sunlight filters through the trees, casting shadows across the well-maintained grass. The approach to the front door is framed by decorative shrubs and flowers, suggesting a warm, inviting entrance.

Home in Winston-Salem

4.87 out of 5 average rating, 135 reviews

The Page’s House

The kitchen area is equipped with black cabinetry and stainless steel appliances. A circular table with four wooden chairs is positioned on a patterned rug. A ceiling fan and natural light from the window enhance the inviting atmosphere.

Home in West Salem

4.94 out of 5 average rating, 108 reviews

Comfort & Convenience in this 3BR Brick Ranch

Other great vacation rentals in Winston-Salem

A cozy bedroom features a wooden bed with a light blue bedding set. A ceiling fan illuminates the space, complemented by two bedside lamps. A piece of artwork depicting birds adds a touch of nature, while natural light enters through a small window.

Condo in Ardmore

4.89 out of 5 average rating, 282 reviews

Charming quiet condo all to yourself

Top guest favorite

The spacious living area showcases wooden log walls and a warm atmosphere. A stone fireplace is centrally located, with a patterned area rug beneath a comfortable sofa. Large windows allow natural light to illuminate the room, while rustic decor complements the cabin's character.

Cabin in Winston-Salem

4.96 out of 5 average rating, 213 reviews

Majestic Getaway near Wake Forest University

The cozy cottage is illuminated by soft lighting at night, surrounded by lush greenery and well-maintained garden features. Outdoor seating with potted plants sits in the foreground, while the inviting entrance to the cottage is visible through tastefully decorated steps.

Guesthouse in Winston-Salem

4.93 out of 5 average rating, 864 reviews

Courtyard Cottage Safe Parking! No pet fees!

Top guest favorite

A spacious living area features a light-colored sectional sofa adorned with decorative pillows. A wooden coffee table with a geometric pattern is positioned in front, complementing the beamed ceiling. A view of the kitchen area is visible through an archway, enhancing the open floor plan.

Home in Winston-Salem

4.99 out of 5 average rating, 195 reviews

The Zen Ranch - Spacious Layout with Modern Decor

Top guest favorite

An inviting kitchen area features modern appliances, including a stainless steel refrigerator and microwave. A granite-topped island with two black stools provides space for dining or preparation. Wooden shelves showcase dishware against a white tiled backsplash, complemented by warm wood cabinetry and natural light from a window.

Guest suite in Ardmore

4.98 out of 5 average rating, 99 reviews

Bright and refreshing apartment in Ardmore

Top guest favorite

A view from the loft captures a vibrant urban landscape, featuring a green park area bordered by modern buildings. Vehicles are parked along the neatly paved roads, while pedestrians can be seen enjoying the open space under a clear blue sky.

Loft in Winston-Salem

4.99 out of 5 average rating, 98 reviews

Lovely 1 bedroom loft in Downtown, Winston-Salem

Top guest favorite

The modern farmhouse exterior features a stepped roof with a metal finish, complemented by inviting covered porches. Lush greenery and ornamental plants line the pathway, while a broad grassy area extends, providing a serene connection to nature.

Home in Lexington

4.98 out of 5 average rating, 116 reviews

Duke's Place - Tranquil Farmhouse Retreat

The kitchen features rustic wooden cabinetry and a large central island with matching wooden benches. Stainless steel appliances are included, with a microwave and stovetop visible. Pendant lights illuminate the space, creating a warm and welcoming atmosphere.

Cabin in Ardmore

4.89 out of 5 average rating, 850 reviews

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

Quick stats about vacation rentals in Winston-Salem

Total rentals
1K properties
Total number of reviews
46K reviews
Family-friendly rentals
560 properties are a good fit for families
Pet-friendly rentals
400 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
620 properties have a dedicated workspace

Frequently Asked Questions

Where should I stay in Winston-Salem?
Make yourself at home in Winston-Salem by choosing from our most frequently booked neighborhoods. We have over 30 vacation rentals in Salem Gardens, over 450 vacation rentals in Ardmore, over 450 vacation rentals in West Salem, and over 240 vacation rentals in Buena Vista.
Are there vacation rentals with a dedicated workspace in Winston-Salem?
Yes! Work meets play with ease at over 620 vacation rentals in Winston-Salem featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winston-Salem?
Four-legged friends are welcome in Winston-Salem. Choose from more than 400 vacation rentals for guests traveling with pets.
Are there Winston-Salem vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Winston-Salem, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in cabin rentals in Winston-Salem?
Experience the best of Winston-Salem with our cabin rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Winston-Salem?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with a bbq area, over 30 homes with a gym, over 130 homes with self check-in, over 570 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Winston-Salem have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winston-Salem have self check-in?
Absolutely! We offer over 130 house rentals with self check-in in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Winston-Salem have a gym?
Absolutely! We offer over 20 apartment rentals with a gym in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Winston-Salem have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore