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, 129 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!

Jan 17 – 24

G$18,637 GYD per night

Guest favorite

Home in Winston-Salem

4.93 out of 5 average rating, 191 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)

Oct 2 – 9

G$34,094 GYD per night

Guest favorite

Guest suite in Winston-Salem

4.99 out of 5 average rating, 210 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.

Nov 5 – 12

G$15,973 GYD per night

Guest favorite

Home in Winston-Salem

4.99 out of 5 average rating, 157 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.

Jul 30 – Aug 6

G$28,987 GYD per night

Guest favorite

Apartment in Winston-Salem

5.0 out of 5 average rating, 245 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!

Oct 1 – 8

G$18,145 GYD per night

Guest favorite

Guest suite in Winston-Salem

4.98 out of 5 average rating, 254 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

Aug 20 – 27

G$20,472 GYD per night

Guest favorite

Condo in Winston-Salem

4.97 out of 5 average rating, 117 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.

Aug 30 – Sep 6

G$20,849 GYD per night

Guest favorite

Condo in Winston-Salem

4.91 out of 5 average rating, 146 reviews

Open Stylish Condo near Old Salem, Downtown, UNCSA

Overlooking historic Old Salem, this spacious 3rd floor condominium offers modern amenities and unique charm. Conveniently located in walking distance to downtown, Salem College, and UNCSA, and just a short drive to WSSU and Wake Forest. Perfect for families, faculties, or college tours. Secure building with elevator access and free parking. You'll love this bright open space, with high ceilings, a full and spacious kitchen, and your own breakfast balcony.

May 6 – 13

G$19,384 GYD per night

Guest favorite

Home in Ardmore

4.98 out of 5 average rating, 408 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.

Aug 9 – 16

G$19,472 GYD per night

Guest favorite

Condo in Winston-Salem

4.95 out of 5 average rating, 353 reviews

A Bright Spot in West End

Welcome to the Shenandoah house condominiums! Located in the historic West End neighborhood of downtown Winston-Salem. Spacious one bedroom with lots of natural light, hardwood floors, eat in kitchen and private screened porch. Filled with works from many of Winston's local artists. Fully equipped for your stay. Easy walking distance to restaurants, bars, shopping, entertainment, breweries, parks and public transportation. Free parking!

May 7 – 14

G$17,190 GYD per night

Guest favorite

Cabin in Winston-Salem

4.99 out of 5 average rating, 139 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!

Sep 6 – 13

G$29,022 GYD per night

Guest favorite

Bungalow in Ardmore

4.97 out of 5 average rating, 352 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.

May 5 – 12

G$30,333 GYD 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

Novant Health Forsyth Medical Center7 locals recommend

Old Salem Museums & Gardens Administrative Offices36 locals recommend

Other great vacation rentals in Winston-Salem

Guest favorite

Guesthouse in Germanton

4.96 out of 5 average rating, 406 reviews

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

Aug 29 – Sep 5

G$17,074 GYD per night

Guest favorite

Guest suite in Winston-Salem

4.99 out of 5 average rating, 505 reviews

The Man Cave

Oct 7 – 14

G$34,848 GYD per night

Guest favorite

Apartment in Winston-Salem

4.96 out of 5 average rating, 213 reviews

West Salem Art Hotel, "Art"partment #1

May 24 – 31

G$24,592 GYD per night

Guest favorite

Guesthouse in Winston-Salem

4.94 out of 5 average rating, 299 reviews

Studio 1BR near WFU

Dec 8 – 15

G$19,294 GYD per night

Guest favorite

Condo in Winston-Salem

4.9 out of 5 average rating, 380 reviews

Sanctuary – 1bedroom & 1bathroom

Sep 26 – Oct 3

G$22,332 GYD per night

Guest favorite

Condo in Winston-Salem

4.9 out of 5 average rating, 247 reviews

Charming quiet condo all to yourself

Mar 27 – Apr 3

G$11,623 GYD per night

Guest favorite

Apartment in Winston-Salem

4.88 out of 5 average rating, 408 reviews

Summit Street Garden Apartment

Jul 6 – 13

G$23,474 GYD per night

Guest favorite

Home in Winston-Salem

4.9 out of 5 average rating, 144 reviews

Old Salem Restored Moravian Village 1700s

Apr 23 – 30

G$28,819 GYD per night

Show all

Other great vacation rentals in Winston-Salem

Guest favorite

Home in Winston-Salem

4.97 out of 5 average rating, 77 reviews

Peaceful house minutes from Wake Forest University

Jun 29 – Jul 6

G$25,741 GYD per night

Guest favorite

Apartment in Winston-Salem

5.0 out of 5 average rating, 40 reviews

Renovated King | Walk Downtown & Baptist Hospital!

Dec 16 – 23

G$20,564 GYD per night

Superhost

Home in Winston-Salem

5.0 out of 5 average rating, 3 reviews

The Mint Julip: Country Classic

Oct 6 – 13

G$29,132 GYD per night

Superhost

Apartment in Winston-Salem

4.78 out of 5 average rating, 37 reviews

Zen 1 BR in heart of Winston-Salem - Parking!

Mar 13 – 20

G$17,402 GYD per night

Guest favorite

Apartment in Winston-Salem

4.93 out of 5 average rating, 29 reviews

Charming Historic West End Apt C, main level

Oct 6 – 13

G$25,610 GYD per night

Guest favorite

Home in Winston-Salem

5.0 out of 5 average rating, 8 reviews

Updated 1BR cottage on private acre+ lot

Aug 25 – Sep 1

G$20,179 GYD per night

Guest favorite

Guest suite in Winston-Salem

5.0 out of 5 average rating, 14 reviews

Hen & Roost Inn (Near Wash Park, UNCSA, Old Salem)

Jun 1 – 8

G$19,028 GYD per night

Guest favorite

Apartment in West Salem

4.98 out of 5 average rating, 53 reviews

Vintage Grocery-now Artsy downtown Apt near UNCSA

Oct 4 – 11

G$24,640 GYD 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 240 vacation rentals in Buena Vista, 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 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 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 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 20 apartment rentals with a gym in Winston-Salem. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Winston-Salem have wifi?
Absolutely! We offer over 30 townhouse 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

Cabins

Apartments

Popular amenities for Winston-Salem vacation rentals

Stay near Winston-Salem's top sights

Other great vacation rentals in Winston-Salem

Guesthouse in Germanton

Guest suite in Winston-Salem

Apartment in Winston-Salem

Guesthouse in Winston-Salem

Condo in Winston-Salem

Condo in Winston-Salem

Apartment in Winston-Salem

Home in Winston-Salem

Other great vacation rentals in Winston-Salem

Home in Winston-Salem

Apartment in Winston-Salem

Home in Winston-Salem

Apartment in Winston-Salem

Apartment in Winston-Salem

Home in Winston-Salem

Guest suite in Winston-Salem

Apartment in West 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 bungalow 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 apartment rentals in Winston-Salem have self check-in?

Do apartment rentals in Winston-Salem have a gym?

Do townhouse rentals in Winston-Salem have wifi?

Destinations to explore