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Vacation rentals in Winston-Salem

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winston-Salem vacation rentals

Self check-in
Pet friendly
Hot tub
Monthly stays
Laptop-friendly workspace

Pet-friendly vacation rentals in Winston-Salem

Top guest favorite
The cabin features a dark wood exterior, complemented by large windows reflecting the warm glow of the setting sun. Surrounding foliage adds a natural touch, while tall grasses in the foreground enhance the serene outdoor environment.
Cabin in Danbury
4.98 out of 5 average rating, 164 reviews

The Rocking A Frame - modern meets cozy

Guest favorite
The inviting exterior of a 1940's cape cod home is framed by lush greenery and blooming azaleas. The brick facade features white shutters and a welcoming front porch. A pathway leads to the entrance, creating a sense of approachability.
Home in Winston-Salem
4.87 out of 5 average rating, 212 reviews

*CHARMING* 3bd dogfriendly entire HOME close to DT

Top guest favorite
A comfortable living room features leather seating and a wooden entertainment unit. Two side tables with lamps flank a cozy chair, providing warm lighting. A decorative painting hangs on the wall, and a small plant adds a touch of greenery. The laminate flooring creates a unified look.
Home in Winston-Salem
4.96 out of 5 average rating, 163 reviews

Cozy 3 Bedroom Home with Fenced Back Yard

Top guest favorite
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
4.99 out of 5 average rating, 133 reviews

Entire Private Entrance Studio Apartment with Pool

Guest favorite
The exterior features a welcoming entrance with a set of green chairs positioned on a wooden porch. A gravel walkway leads to the front steps, surrounded by landscaped mulch and small plants. The house is framed by lush green trees.
Home in Winston-Salem
4.96 out of 5 average rating, 174 reviews

Deacon Stays: The Brookwood - Walk to WFU

Top guest favorite
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
4.97 out of 5 average rating, 115 reviews

“Home” on the Road!

Top guest favorite
A charming log cabin sits on an expansive grassy area, featuring a porch with two blue chairs and small tables. In the foreground, pumpkins are placed decoratively, while a shed is visible to the right, surrounded by vibrant autumn foliage.
Cabin in Pinnacle
4.96 out of 5 average rating, 224 reviews

A Squirrels Paradise

Top guest favorite
A warm-toned wood-paneled interior is visible, featuring a cozy sleeping area with a bed covered in a patterned blanket. Two blue chairs are positioned nearby, complemented by a round ottoman. Natural light filters through window coverings, enhancing the inviting atmosphere.
Tiny home in Thomasville
4.95 out of 5 average rating, 216 reviews

The Shack at Abiding Place - So Cozy and Peaceful

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Vacation rentals with jacuzzis in Winston-Salem

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.
Home in Winston-Salem
4.89 out of 5 average rating, 289 reviews

Cozy King Blue H2O Staycation , Pool & Hot Tub

Top guest favorite
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
4.98 out of 5 average rating, 138 reviews

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

Guest favorite
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
4.92 out of 5 average rating, 252 reviews

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

Guest favorite
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
4.9 out of 5 average rating, 177 reviews

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

Top guest favorite
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
4.99 out of 5 average rating, 128 reviews

Cozy renovated 3 bedroom cabin with hot tub

Guest favorite
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
4.9 out of 5 average rating, 173 reviews

Farm Studio w/hot tub & fenced yard

Guest favorite
A serene outdoor space features a hot tub surrounded by wooden decking. A projected movie screen displays an ocean scene, illuminated by soft lights. The area presents a perfect setting for relaxation and entertainment at night.
Home in High Point
4.88 out of 5 average rating, 258 reviews

Wayne's Place-Hot tub, pet friendly. Close to HPU

Top guest favorite
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
5 out of 5 average rating, 356 reviews

Mountain View Retreat

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Other great vacation rentals in Winston-Salem

Guest favorite
An inviting outdoor seating area features a cozy loveseat adorned with cushions. A small round table sits beside the loveseat, accompanied by decorative plants. A hammock is suspended nearby, and various greenery frames the space, creating a serene atmosphere in the courtyard.
Guesthouse in Winston-Salem
4.93 out of 5 average rating, 856 reviews

Courtyard Cottage Safe Parking! No pet fees!

Superhost
A charming, single-story home is surrounded by a lush green yard and shaded by trees. The exterior features a light-colored facade with a welcoming porch area, and mature landscaping lines the property, enhancing the inviting atmosphere.
Home in Winston-Salem
4.81 out of 5 average rating, 205 reviews

Winston posh bungalow near Wake

Guest favorite
The back deck features a large rectangular table surrounded by six chairs, all situated on red wooden flooring. A spacious view of the green backyard and surrounding trees is visible, providing an opportunity for outdoor gatherings.
Home in Winston-Salem
4.97 out of 5 average rating, 175 reviews

Beautiful 2 BR home with Office and Game Room

Guest favorite
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
4.93 out of 5 average rating, 183 reviews

"Deacon House" 3 bedrooms

Top guest favorite
A welcoming entrance is framed by a dark door against a brick wall. Two cushioned chairs with patterned pillows sit beside a small table. Potted plants add touches of greenery, creating a cozy outdoor seating area.
Guest suite in Pfafftown
4.97 out of 5 average rating, 204 reviews

The Colonial Winston-Salem: a boutique guest suite

Guest favorite
A modern bathroom features a spacious walk-in shower enclosed by glass panels. Elegant marble tiles line the walls and floor, complemented by a marble vanity with dual sinks. The shower includes a rainfall showerhead and a built-in bench. Two artistic pieces adorn the walls.
Guest suite in Winston-Salem
4.99 out of 5 average rating, 134 reviews

West End Jewel - Large 1 Bed/1 Bath Near Everything!

Guest favorite
Two brown horses are harnessed in front of a carriage, showcasing a traditional setup. The horses are adorned with harnesses featuring red accents. A historical brick building is visible in the background, framed by trees that are bare of leaves.
Home in Winston-Salem
4.91 out of 5 average rating, 173 reviews

Old Salem Restored Moravian Village 1700s

Top guest favorite
A hallway is featured, showcasing neutral wall colors and wooden flooring. A clock hangs on the left wall, while a mirror with a decorative frame is positioned across the corridor. This space offers a view into another room, enhancing the sense of openness.
Home in Winston-Salem
4.98 out of 5 average rating, 108 reviews

Elegant Pet Friendly Ranch close to everything!

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Quick stats about vacation rentals in Winston-Salem

  • Total rentals

    1K properties

  • Total number of reviews

    44K reviews

  • Family-friendly rentals

    550 properties are a good fit for families

  • Pet-friendly rentals

    390 properties allow pets

  • Rentals with a pool

    60 properties have a pool

  • Rentals with dedicated workspaces

    630 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 240 vacation rentals in Buena Vista, over 30 vacation rentals in Salem Gardens, over 450 vacation rentals in Ardmore, and over 450 vacation rentals in West Salem.

  • Are there vacation rentals with a dedicated workspace in Winston-Salem?

    Yes! Work meets play with ease at over 630 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 390 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in guesthouse rentals in Winston-Salem?

    Experience the best of Winston-Salem with our guesthouse rentals, starting at about $70 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 Apartment Rentals in Winston-Salem?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with self check-in, over 10 homes with a gym, 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.

  • Are there Winston-Salem apartment rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 apartment rentals with pools in Winston-Salem, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Winston-Salem have self check-in?

    Absolutely! We offer over 140 house rentals with self check-in in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winston-Salem have a gym?

    Absolutely! We offer over 40 house rentals with a gym in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly apartment rentals in Winston-Salem?

    Winston-Salem has more than 50 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore