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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
Monthly stays
Laptop-friendly workspace
Gym

Stay near Winston-Salem's top sights

Wake Forest University48 locals recommend
Old Salem Visitor Center149 locals recommend
Reynolda House Museum of American Art99 locals recommend
Benton Convention Center8 locals recommend
Village Tavern84 locals recommend
Whole Foods Market64 locals recommend

Pet-friendly vacation rentals in Winston-Salem

Guest favorite
Farm stay in Greensboro
4.94 out of 5 average rating, 315 reviews

Arya’s cottage with a loft & jacuzzi

Guest favorite
Home in Walnut Cove
4.93 out of 5 average rating, 102 reviews

Modern and Spacious cottage, centrally located

Guest favorite
Home in Winston-Salem
4.96 out of 5 average rating, 156 reviews

Cozy 3 Bedroom Home with Fenced Back Yard

Guest favorite
Guesthouse in Winston-Salem
4.94 out of 5 average rating, 835 reviews

Courtyard Cottage Safe Parking! No pet fees!

Guest favorite
Home in Winston-Salem
4.81 out of 5 average rating, 197 reviews

Winston posh bungalow near Wake

Guest favorite
Guesthouse in Mocksville
4.97 out of 5 average rating, 108 reviews

“Home” on the Road!

Guest favorite
Guesthouse in Germanton
4.96 out of 5 average rating, 478 reviews

Mel’s country cottage. Country life near the city.

Guest favorite
Guesthouse in Archdale
4.98 out of 5 average rating, 170 reviews

Hillbilly Hideout

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Other great vacation rentals in Winston-Salem

Guest favorite
Home in High Point
5 out of 5 average rating, 10 reviews

The Wooded Grand

Guest favorite
Home in Winston-Salem
4.93 out of 5 average rating, 27 reviews

Peacefulness of Country Club Rd

Superhost
Cabin in Winston-Salem
4.86 out of 5 average rating, 59 reviews

Cheerful 2 bedroom cabin with indoor fireplace

Guest favorite
Home in Belews Creek
4.86 out of 5 average rating, 51 reviews

Belews Lake Paradise

Guest favorite
Home in Greensboro
4.95 out of 5 average rating, 22 reviews

Vintage Chic Cottage < 1 Mile to UNC Greensboro!

Guest favorite
Tiny home in Jamestown
4.95 out of 5 average rating, 291 reviews

Tiny House

Guest favorite
Home in Jamestown
4.94 out of 5 average rating, 16 reviews

The Arlington Oasis | Sport Court + HotTub + Golf

Guest favorite
Home in Greensboro
4.98 out of 5 average rating, 133 reviews

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

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Quick stats about vacation rentals in Winston-Salem

  • Total rentals

    990 properties

  • Total number of reviews

    44K reviews

  • Family-friendly rentals

    540 properties are a good fit for families

  • Pet-friendly rentals

    380 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 250 vacation rentals in Buena Vista, over 440 vacation rentals in Ardmore, over 30 vacation rentals in Salem Gardens, and over 440 vacation rentals in West Salem.

  • 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 380 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 condo rentals in Winston-Salem?

    Experience the best of Winston-Salem with our condo rentals, starting at about $20 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 10 homes with a gym, over 40 homes with self check-in, 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 70 house rentals with a bbq area in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.

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

    Absolutely! We offer over 40 apartment 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 10 apartment rentals with a gym in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.

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

    Winston-Salem has more than 20 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore