
Vacation rentals in Winston-Salem
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Top-rated vacation rentals in Winston-Salem
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Vacation rentals for every style
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Popular amenities for Winston-Salem vacation rentals
Pet-friendly vacation rentals in Winston-Salem

Cozy 3 Bedroom Home with Fenced Back Yard
This is our second stay here and love the place. It has the older home charm that is so tastefully decorated. The kitchen has it all! Roomy and private. Sitting on the back porch watching the dogs run around the back yard is great! The fenced yard is large and very cleared our and safe for the pups, mine loved it! I could go on and on but find out for yourself! You may even make a sweet friend next door! Such a personable person!

Courtyard Cottage Safe Parking! No pet fees!
She is a wonderful person and let us feel right at home. Tgank you so very much. Enjoyed chatting with you....ride a harley...lol

Winston posh bungalow near Wake
Wow I have been using Air B&B for years, and Ryan is the best host EVER. He went out of his way to make sure we were able to get to the location, and even met one of us at the site and did a walk through on arrival!! So super helpful, responsive, clear communications. Great house, quiet, private, comfortable, welcoming and and for us in particular it was 8 minutes from the conference we were attending. Ryan was also kind and understanding; I forgot to do something and he was super gracious about it. Best EVER!!

“Home” on the Road!
This place was clean and in a good area. It had everything I needed for a longer stay. Peggy was great!

Cozy Relaxing Retreat Your Charming Tiny Getaway
We had an amazing stay at this cozy tiny home! The host was incredibly kind and helpful, making sure we had everything we needed for a comfortable visit. The space was spotless and had all the essentials. It was the perfect spot for a peaceful getaway, and we truly appreciated the quiet surroundings. From start to finish, the hospitality made our experience even better. We would definitely recommend this stay to anyone looking for a relaxing retreat. Thank you for making our visit so wonderful!

Klump Farm Cabin
I had a marvelous stay at Connie and Gene’s. This cute little cabin looks impossibly small from the outside, but the inside is spacious, with a high ceiling. It’s the perfect cabin for a couple or small family, with tons of outdoor space for relaxing, playing games, or taking a walk. The inside of the cabin is super cozy and the decor is chic and understated. The bathroom is adorable with a big claw foot tub that I really enjoyed soaking in. It was a very quiet, and peaceful stay. It’s obvious that Connie and Gene keep their guest’s comfort in mind - there were lots of snacks, farm fresh eggs, wine, coffee, butter and water in the house along with a number of other items. They were responsive whenever I reached out and were even so kind as to reach out the morning of my check out and let me know I could delay my departure a bit if needed due to a band of storms that were coming through the area. I would definitely consider visiting again, and plan to book another visit one day!

Hillbilly Hideout
Had a wonderful time at this cute little cabin! It’s so peaceful and in a convenient location that’s not far from the city. And you still have the privacy of being in the country. Would recommend to anyone :)

Cozy chic log cabin overlooking horse pastures
Beautiful property and home was perfectly clean and just as described...thank you!
House rentals in Winston-Salem

Perfect Greensboro location Entire Townhome
The townhome was great. It was so clean and cozy. It’s in a nice, quiet residential neighborhood close to grocery stores and restaurants. Kristin is a wonderful host. She responds quickly and checks in with you throughout your stay. I would definitely stay here again.

CasaLuna: Graduation & Summer ready in GSO!
Very nice place. Would definitely stay again. Only issue was with the heat. It was very cold outside when we traveled. If you close the bedroom doors at night, 2 of the bedrooms are freezing cold and the vents do not allow heat into those bedrooms. We slept with the doors open on the second night of our stay and had no issues but something to keep in mind for future travelers.

Big House Downtown! 6BR 3BTH!
Nice place in a great central location. Didn’t realize it was two separate units that didn’t have a way to access each without walking outside but we made it work.

Premier New Home close to WFU w/ Lvl 2 EV Charger
Our family stayed at this beautiful home while visiting Wake Forest. The home was absolutely beautiful inside and out, including such a peaceful exterior with outdoor sitting amongst the trees. Each room looked exactly as the photos, and was extremely clean. Our family couldn’t stop admiring how nicely decorated the home was, and cannot wait to book again for our next trip to Winston Salem!

Quaint 2 bed 1 bath cottage style home
I travel to Kernersville once a month and stay in AirBnBs. Definitely adding Oak Street to the preferred list. Great house and very accommodating for dogs. Very clean. Growing up in K-ville, I can assure any future guests, the area is safe and walkable.

High Point Hideaway
This house was a great fit for my needs and matched the description and reviews. Host is very responsive. House was very clean with lots of sunlight. Quiet neighborhood.

Spacious Townhouse In High Point Near HPU & Market
I had a great stay at Chase’s place. We had a bit of an issue when we first arrived, but Chase was very responsive and got it taken care of right away. The place is cute and cozy, and was pretty convenient to where I needed to be. Would definitely book again!

Great house with huge yard in good location!
This place was amazing and very close to our family. It definitely was a very cozy home away from home.
Pet-friendly house rentals Winston-Salem

Tranquil 3 Bed, 2 Bath with High-speed Internet
John and Paula were very attentive hosts. The house was lovely and the space well outfitted. We very much appreciated the coffee, baby items and comfortable rooms. It was easy to get in and well located for various events we had in Winston-Salem. The yard is lovely and we would have spent more time there if it weren’t a bit chilly and we didn’t have so many events to attend. If we need to return to Winston we would definitely come back to their home.

*CHARMING* 3bd dogfriendly entire HOME close to DT
Great place to stay - a home away from home. House was perfect if you have dogs, the fenced in yard made the stay super easy.

The Poet's House, Luxury and Solitude on 100 acres
We had the loveliest of times at The Poet’s House. The location is amazing, private, surrounded by nature but close to all we needed. The house is so beautiful, peaceful and has incredible energy, it’s beautifully decorated making it a very pleasant environment to rest and relax. The beds were very comfortable, lots of amenities, complete kitchen, extra pillows and towels, etc. The best thing is the hosts! Always responsive and kind, flexible, very helpful and welcoming. We would love to stay here again.

Deacon Stays: The Brookwood - Walk to WFU
Great location with plenty of space. Plenty of room to host a large group.

Luxe Hot Tub 4BR: Ideal for Market, HPU & Families
We booked this stay at the last minute and we were so pleased with the experience! The host team is phenomenal! They checked on us before arrival, went to the house and turned some lights on (knowing we were arriving late), explained in detail and communicated very well, and the space was great! The hot tub was an added bonus to relax in after a long travel day, the toy bin was so great for my 2 year old, and the bed was the most comfortable bed I have slept in! I would 100% stay here again!!

Chapman Charmer- 2 QN, Walk to Coliseum & UNCG
This cozy little home was walking distance to the coliseum. Host was very responsive and helpful. Waters were stocked and ready for us which came in very handy. The place was super clean and tidy.

Adorable, Stylish near UNCSA and Downtown
Nicer than advertised! Beautiful renovation. Cozy even in cold weather!

The Hen House
Allison is a great host! I booked late, due to water issues in my home, and she worked quickly to make it happen. The home is in a nice neighborhood, with friendly neighbors. The fenced backyard was great for my dog, and Allison had folks there working hard to clean up debris from the storm that occurred the day before! I enjoyed the sunroom and the deck during my stay.
Quick stats about vacation rentals in Winston-Salem
Total rentals
1K 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.
What types of vacation rentals are available in Winston-Salem?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Winston-Salem. From over 160 apartment rentals to over 590 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
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.
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 House Rentals in Winston-Salem?
Enhance your stay in our House Rentals with the most popular amenities: over 140 homes with self check-in, over 580 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do guesthouse rentals in Winston-Salem have air conditioning?
Absolutely! We offer over 10 guesthouse rentals with air conditioning 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 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.
Are there family-friendly condo rentals in Winston-Salem?
Winston-Salem has more than 20 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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