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.

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Guest favorite

Guest suite in Pfafftown

4.97 out of 5 average rating, 135 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!

Nov 30 – Dec 7

R1,642 ZAR per night

Guest favorite

Home in Winston-Salem

4.92 out of 5 average rating, 195 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)

Aug 22 – 29

R3,197 ZAR per night

Guest favorite

Guest suite in Winston-Salem

4.99 out of 5 average rating, 212 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.

Oct 15 – 22

R1,472 ZAR per night

Guest favorite

Guest suite in Winston-Salem

4.99 out of 5 average rating, 512 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 30 – Oct 7

R2,436 ZAR per night

Guest favorite

Home in Winston-Salem

4.99 out of 5 average rating, 159 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.

Aug 9 – 16

R2,592 ZAR per night

Guest favorite

Apartment in Winston-Salem

5.0 out of 5 average rating, 247 reviews

Bright & Cozy Upstairs Apartment/Near Downtown

Sunny one-bedroom apartment on 2nd floor of historic home. Close to downtown & WFU/Baptist Hospital. You'll have the whole place to yourself, with a private entrance and coded deadbolt for keyless entry. Open living area with full-sized futon. Kitchen equipped with stove, oven, full-sized fridge & microwave. Coffee, tea, and snacks provided. Separate bedroom with queen-sized bed. Bathroom with full-sized shower/tub and washer/dryer. Off-street parking available. Welcome home!

Sep 14 – 21

R1,644 ZAR per night

Guest favorite

Guest suite in Winston-Salem

4.98 out of 5 average rating, 258 reviews

Ardmore studio, close to downtown, hospitals & WFU

This unique studio space is located in the historic Ardmore district conveniently located minutes from both Forsyth and Baptist hospitals, downtown and WFU. It is also a short stroll to Ardmore coffee shop, Carlisles pub, Arthur’s diner, famous PB’s hot dogs and burgers, groceries and other conveniences! Private entrance with keyless entry, street parking and 1 guest space on grounds. Queen bed & fold down couch. Fridge/freezer, microwave, toaster/toaster oven, coffee pot, kettle

Feb 24 – Mar 3

R1,840 ZAR per night

Guest favorite

Condo in Winston-Salem

4.97 out of 5 average rating, 118 reviews

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.

Oct 4 – 11

R1,881 ZAR per night

Guest favorite

Home in Winston-Salem

4.98 out of 5 average rating, 410 reviews

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.

Oct 5 – 12

R1,720 ZAR per night

Guest favorite

Apartment in Winston-Salem

4.96 out of 5 average rating, 216 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.

Jun 14 – 21

R2,296 ZAR per night

Guest favorite

Cabin in Winston-Salem

4.99 out of 5 average rating, 141 reviews

The Blue Door Cabin

This tiny cabin is brand new and nestled just inside the woods, but only 1/2 mile from I-74 and only 10 min. to downtown Winston Salem, NC. This little cabin was built just for Airbnb guests, it has granite tops, stained concrete floors, a beautiful tiled/stone shower, and will surely help you unwind and enjoy your stay in this delightful space!

Jan 14 – 21

R2,622 ZAR per night

Guest favorite

Bungalow in Winston-Salem

4.97 out of 5 average rating, 355 reviews

Cozy Ardmore Bungalow

Come explore this renovated 1925 bungalow in the historic Ardmore Neighborhood . This sunlit, plant filled home boasts a modern kitchen with concrete counters, gas stove, and hand built wooden furniture. The fenced backyard features a stone patio with fire pit and grill. Smart TVs in each bedroom and living room. Pets are welcome.

Dec 21 – 28

R2,833 ZAR per night

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

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Winston-Salem's top sights

Hanes Mall57 locals recommend

Lawrence Joel Veterans Memorial Coliseum13 locals recommend

Benton Convention Center8 locals recommend

Washington Park9 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

Condo in Winston-Salem

4.95 out of 5 average rating, 355 reviews

A Bright Spot in West End

May 24 – 31

R1,672 ZAR per night

Guest favorite

Guesthouse in Germanton

4.96 out of 5 average rating, 411 reviews

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

Dec 24 – 31

R1,547 ZAR per night

Guest favorite

Home in Winston-Salem

4.97 out of 5 average rating, 132 reviews

Cozy 3 Bedroom Home with Fenced Back Yard

May 6 – 13

R2,763 ZAR per night

Guest favorite

Apartment in Winston-Salem

4.92 out of 5 average rating, 108 reviews

Entire Apartment near Atrium Baptist Hospital

Oct 29 – Nov 5

R2,188 ZAR per night

Guest favorite

Condo in Winston-Salem

4.9 out of 5 average rating, 384 reviews

Sanctuary – 1bedroom & 1bathroom

Aug 24 – 31

R1,814 ZAR per night

Guest favorite

Guesthouse in Winston-Salem

4.94 out of 5 average rating, 301 reviews

Studio 1BR near WFU

Nov 2 – 9

R1,781 ZAR per night

Guest favorite

Home in Winston-Salem

4.97 out of 5 average rating, 132 reviews

Beautiful 2 BR home with Office and Game Room

Jul 30 – Aug 6

R2,582 ZAR per night

Guest favorite

Farm stay in Greensboro

4.96 out of 5 average rating, 214 reviews

Arya’s cottage with a loft & jacuzzi

Jan 4 – 11

R2,246 ZAR per night

Show all

Other great vacation rentals in Winston-Salem

Guest favorite

Guest suite in Winston-Salem

4.88 out of 5 average rating, 103 reviews

Cozy Private Room with Suite

Jan 2 – 9

R1,576 ZAR per night

Guest favorite

Apartment in Winston-Salem

4.88 out of 5 average rating, 412 reviews

Summit Street Garden Apartment

Jun 7 – 14

R1,954 ZAR per night

Guest favorite

Guesthouse in Clemmons

4.96 out of 5 average rating, 114 reviews

Bee Happy- Studio & Pets Welcome- No cleaning Fees

Aug 3 – 10

R2,482 ZAR per night

Guest favorite

Cabin in Pinnacle

4.97 out of 5 average rating, 169 reviews

A Squirrels Paradise Spring Specials

Mar 19 – 26

R1,319 ZAR per night

Guest favorite

Home in Winston-Salem

4.99 out of 5 average rating, 122 reviews

The Zen Ranch - Modern Luxury with Relaxing Vibes

Jul 8 – 15

R3,821 ZAR per night

Guest favorite

Home in Clemmons

4.99 out of 5 average rating, 134 reviews

Kenbridge Single Story

Jun 24 – Jul 1

R2,672 ZAR per night

Guest favorite

Apartment in Winston-Salem

5.0 out of 5 average rating, 64 reviews

The Peaceful Palm - King | Downtown Winston!

Feb 4 – 11

R1,959 ZAR per night

Guest favorite

Guest suite in Winston-Salem

4.92 out of 5 average rating, 50 reviews

Entire COZY Unit - 3 min walk to WFU.

Sep 6 – 13

R1,994 ZAR per night

Show all

Quick stats about vacation rentals in Winston-Salem

Total rentals
940 properties
Rentals with dedicated workspaces
590 properties have a dedicated workspace
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
370 properties allow pets
Family-friendly rentals
500 properties are a good fit for families
Total number of reviews
36K 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 440 vacation rentals in Ardmore, over 30 vacation rentals in Salem Gardens, over 440 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 590 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 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 private suite rentals in Winston-Salem?
Experience the best of Winston-Salem with our private suite 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 50 homes with wifi, over 10 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 house rentals in Winston-Salem have self check-in?
Absolutely! We offer over 150 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 30 house 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 520 house rentals with wifi in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.

Winston-Salem vacation rentals

Top-rated vacation rentals in Winston-Salem

Vacation rentals for every style

Houses

Apartments

Cabins

Popular amenities for Winston-Salem vacation rentals

Stay near Winston-Salem's top sights

Other great vacation rentals in Winston-Salem

Condo in Winston-Salem

Guesthouse in Germanton

Home in Winston-Salem

Apartment in Winston-Salem

Condo in Winston-Salem

Guesthouse in Winston-Salem

Home in Winston-Salem

Farm stay in Greensboro

Other great vacation rentals in Winston-Salem

Guest suite in Winston-Salem

Apartment in Winston-Salem

Guesthouse in Clemmons

Cabin in Pinnacle

Home in Winston-Salem

Home in Clemmons

Apartment in Winston-Salem

Guest suite in Winston-Salem

Quick stats about vacation rentals in Winston-Salem

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Where should I stay in Winston-Salem?

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

Are there pet-friendly vacation rentals in Winston-Salem?

Are there Winston-Salem vacation rentals on Airbnb with pools?

How much does it cost to stay in private suite rentals in Winston-Salem?

What are the most popular amenities for Condo Rentals in Winston-Salem?

Do house rentals in Winston-Salem have a bbq area?

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

Do house rentals in Winston-Salem have a gym?

Do house rentals in Winston-Salem have wifi?

Destinations to explore