Winston-Salem vacation rentals

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Top-rated vacation rentals in Winston-Salem

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

Guest favorite

Guest suite in Pfafftown

4.97 out of 5 average rating, 124 reviews

The Colonial Winston-Salem: a boutique guest suite

A beautifully decorated basement suite 15 minutes from downtown Winston, near Lewisville and some of the best wineries! The space is entirely yours, complete with a charming patio, kitchenette, full bathroom, and studio bedroom/living room. Sit out on the patio with a cup of coffee from our fully stocked coffee bar and watch the deer & birds, or grab a book and snuggle in cozy bedding. We are an active family with dogs & kids living upstairs, so we've provided everything you need for quiet!

Dec 12 – 19

G$19,051 GYD per night
Guest favorite

Home in Winston-Salem

4.94 out of 5 average rating, 182 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 . A fire pit to unwind. Double Hammock & Enjoy a 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)

Nov 20 – 27

G$33,613 GYD per night
Guest favorite

Guest suite in Winston-Salem

4.99 out of 5 average rating, 501 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.

Sep 17 – 24

G$27,718 GYD per night

Popular amenities for Winston-Salem vacation rentals

Stay near Winston-Salem's top sights

Hanes Mall57 locals recommend
Lawrence Joel Veterans Memorial Coliseum13 locals recommend
Benton Convention Center8 locals recommend
Novant Health Forsyth Medical Center7 locals recommend
Old Salem Museums & Gardens Administrative Offices36 locals recommend
Winston Salem Fairgrounds Annex3 locals recommend

Other great vacation rentals in Winston-Salem

Guest favorite

Guest suite in Winston-Salem

4.98 out of 5 average rating, 247 reviews

Ardmore studio, close to downtown, hospitals & WFU

Aug 19 – 26

G$20,515 GYD per night
Guest favorite

Home in Ardmore

4.98 out of 5 average rating, 403 reviews

Camel City Cottage - located near the hospitals

Aug 1 – 8

G$19,635 GYD per night
Guest favorite

Condo in Winston-Salem

4.9 out of 5 average rating, 245 reviews

Charming quiet condo all to yourself

Mar 1 – 8

G$11,647 GYD per night
Guest favorite

Condo in Winston-Salem

4.97 out of 5 average rating, 114 reviews

Old Salem Getaway - Visit DTWS via the Strollway

Jun 20 – 27

G$24,374 GYD per night
Guest favorite

Home in Winston-Salem

4.9 out of 5 average rating, 187 reviews

House in Sunnyside W-S w/Brewery Tour and Tasting!

Dec 31 – Jan 7

G$25,208 GYD per night
Guest favorite

Home in Winston-Salem

4.99 out of 5 average rating, 155 reviews

Salem Twin Deck

Aug 23 – 30

G$30,091 GYD per night
Guest favorite

Tiny home in Winston-Salem

4.87 out of 5 average rating, 246 reviews

Roost20 @ The Tiny House Farm

Jan 10 – 17

G$29,662 GYD per night
Guest favorite

Farm stay in Greensboro

4.95 out of 5 average rating, 198 reviews

Arya’s cottage with a loft & jacuzzi

Aug 5 – 12

G$24,118 GYD per night
Guest favorite

Home in Winston-Salem

4.98 out of 5 average rating, 127 reviews

Beautiful 2 BR home with Office and Game Room

Jul 13 – 20

G$29,484 GYD per night
Guest favorite

Guesthouse in Winston-Salem

4.94 out of 5 average rating, 298 reviews

Studio 1BR near WFU

Oct 15 – 22

G$20,071 GYD per night
Guest favorite

Townhouse in Winston-Salem

5.0 out of 5 average rating, 13 reviews

Spacious Townhouse Close to Everything

Apr 28 – May 5

G$16,814 GYD per night
Guest favorite

Home in Winston-Salem

4.84 out of 5 average rating, 85 reviews

Camilas House

Feb 28 – Mar 7

G$21,962 GYD per night

Other great vacation rentals in Winston-Salem

Guest favorite

Guest suite in Winston-Salem

5.0 out of 5 average rating, 31 reviews

Private guest suite @ Maple Leaf Farm

May 31 – Jun 7

G$24,490 GYD per night
Guest favorite

Apartment in Winston-Salem

4.97 out of 5 average rating, 33 reviews

K-Obscura, Romantic Downtown loft

Jun 6 – 13

G$27,686 GYD per night
Guest favorite

Guest suite in Winston-Salem

4.94 out of 5 average rating, 35 reviews

Entire COZY Unit - 3 min walk to WFU.

May 25 – Jun 1

G$21,593 GYD per night
Guest favorite

Apartment in West Salem

5.0 out of 5 average rating, 52 reviews

Vintage Grocery-now Artsy downtown Apt near UNCSA

May 22 – 29

G$24,967 GYD per night
Guest favorite

Home in Winston-Salem

4.98 out of 5 average rating, 53 reviews

1 Bed Entire Place Ardmore 3 min Baptist Hospital

Sep 4 – 11

G$18,801 GYD per night
Guest favorite

Home in Winston-Salem

5.0 out of 5 average rating, 15 reviews

Cozy and homey house

Apr 3 – 10

G$25,714 GYD per night
Guest favorite

Apartment in Ardmore

4.95 out of 5 average rating, 95 reviews

Spacious 1BR w/ KING Bed Near Hospital & Downtown

Aug 26 – Sep 2

G$29,868 GYD per night
Guest favorite

Home in Ardmore

4.91 out of 5 average rating, 22 reviews

Ardmore Carriage House - 5 Minute walk to Hospital

Aug 6 – 13

G$29,527 GYD per night
Superhost

Guesthouse in Winston-Salem

4.8 out of 5 average rating, 88 reviews

3 mins from Downtown - PS5, King Bed & EV Charger

Jul 9 – 16

G$18,332 GYD per night
Guest favorite

Home in Winston-Salem

4.92 out of 5 average rating, 65 reviews

Cozy home away from home in cul-de-sac community!

Dec 30 – Jan 6

G$24,548 GYD per night
Guest favorite

Home in Winston-Salem

4.93 out of 5 average rating, 43 reviews

Camel City Hideaway

May 29 – Jun 5

G$26,184 GYD per night
Guest favorite

Home in Winston-Salem

4.98 out of 5 average rating, 83 reviews

The Dragonfly in Buena Vista (near BMH & WFU)

Jan 19 – 26

G$24,353 GYD per night

Quick stats about vacation rentals in Winston-Salem

Total rentals

950 properties

Rentals with dedicated workspaces

600 properties have a dedicated workspace

Rentals with a pool

50 properties have a pool

Pet-friendly rentals

370 properties allow pets

Family-friendly rentals

490 properties are a good fit for families

Total number of reviews

38K reviews

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 440 vacation rentals in Ardmore, over 440 vacation rentals in West Salem, and over 30 vacation rentals in Salem Gardens.

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

    Yes! Work meets play with ease at over 600 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 370 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 50 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 bungalow rentals in Winston-Salem?

    Experience the best of Winston-Salem with our bungalow rentals, starting at about $30 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 Condo Rentals in Winston-Salem?

    Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with self check-in, over 50 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 80 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 160 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 30 apartment rentals with a gym in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winston-Salem have wifi?

    Absolutely! We offer over 530 house rentals with wifi in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore