Holiday rentals in Winston-Salem

4.91 out of 5 average rating, 69 reviews

Home in Winston-Salem

The Squirrels Nest: Serene Retreat Near WFU

Welcome to the Squirrel's Nest, your place to relax and unwind after a busy day whether it is work or play. It's easy to imagine that you're in the mountains in this serene cabin nestled in the woods. Just 5 minutes from WFU and 7 from Novant. Pour some cocoa and gather around the fire pit to listen for the distinct hoot from the resident owl. Soak in the tub then fall asleep in a cozy bedroom. In the morning, awake to the sound of birds and dappled sunlight, refreshed and ready for the day.

4.97 out of 5 average rating, 122 reviews

Flat in Winston-Salem

K-Obscura, Romantic Downtown loft

Historic loft in Downtown Winston Salem's Innovation Quarter. Located above Krankies Coffee near WFB Medical School and Bailey Park.Short walking distance to several restaurants and bars. This space has private entrance and patio. Includes complimentary coffee and treat at Krankies. Quiet for a downtown spot with the exception of an occasional train passing through adjacent lot. Includes deep soaking tub, mini-kitchen and comfy king size bed. Space is accessed via stairs. Parking included.

4.99 out of 5 average rating, 582 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.

4.99 out of 5 average rating, 286 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.

Superhost

Cabin in King

4.82 out of 5 average rating, 223 reviews

Cabin with incredible views 30min to Winston-Salem

Escape to our serene cabin at the edge of the world with breathtaking views all around. Just 15 minutes from Hanging Rock and Pilot Mountain State Parks, and 30 minutes from Winston-Salem, enjoy sunrise and sunset from our wrap-around porch, hot tub, or indoors. The open living space features floor-to-vaulted ceiling windows and wood-burning fireplaces. Accommodates 8-10 guests with 3 bedrooms and 3 full bathrooms. New cleaning team. Please note: No pets, no smoking, and no events allowed.

Apartment in Winston-Salem

4.91 out of 5 average rating, 445 reviews

Sanctuary – 1bedroom & 1bathroom

My modern and convenient condo located in the heart of Winston-Salem’s shopping district will provide you with a 1 bedroom & bathroom space. The condo is professionally furnished and cleaned to provide a 5 star experience. Basic appliances provided (microwave, kitchen appliances, washer & dryer, dishwasher, Keurig). Very spacious with patio furniture for extra relaxation! You can also enjoy the community pool and gym. This space is NOT shared. Guests have the entire space to themselves.

4.95 out of 5 average rating, 149 reviews

Entire COZY Unit - 3 min walk to WFU.

Welcome to your cozy - little net. Please keep in mind that this unit is attached to our house (we shared a wall - different entrance). Everything showed in the pictures will be all yours (Master bedroom, Study room - living room Space, and an extraordinary bathroom). When staying at our place, you are: - 3 min drive (10min walk) to WFU Campus. - 5 min drive to Downtown. - 3 min WALK to Stadiums and Restaurants. - 10min drive to Wake Forest Baptist Hospital. - Reynolda House museum.

4.96 out of 5 average rating, 488 reviews

Guest house in Germanton

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

Private detached effeciency apartment in a country setting near WinstonSalem. Queen bed, kitchenette with sink and essentials, sofa, smart TV, full bath, covered porch. Relax by the creek or enjoy nature walks. Watch the occasional deer & other wildlife. Use the grill or fire pit at your leisure. Pets welcome. Local restaurant & convenient store 1 min. away. Close to many tourist destinations- Hanging Rock, Winston Salem, Pilot Mt. Belews Creek power station.

4.97 out of 5 average rating, 575 reviews

Home in Ardmore

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.

Apartment in Winston-Salem

4.94 out of 5 average rating, 371 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!

4.97 out of 5 average rating, 418 reviews

Bungalow in Ardmore

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.

4.99 out of 5 average rating, 198 reviews

Buena Vista In-laws suite

Newly refreshed second-story In-Laws suite above a detached garage. The suite includes hardwood floors, full kitchen, king bed, and a separate living room area. Located on a gated 1/2 acre property on the edge of Winston's highly desirable Buena Vista neighborhood. Guests can use courtyard area for eating, working or talking.

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Popular amenities for Winston-Salem holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Winston-Salem

4.93 out of 5 average rating, 118 reviews

Private room in Ardmore

Private bedroom 5 mins from Wake Forest Hospital

MelissaRating, 5 stars1 week ago

This was one of the best Airbnbs that I’ve ever stayed in, and it was definitely the best in-home, single room stay I’ve ever had. All of the amenities in the room were well appointed, everything was very clean, access in and out of both my room and the house itself was very easy, and the host was delightful – both welcoming and unobtrusive. The location was safe, convenient to multiple locations, and very quiet. I used to live in Winston-Salem and was back to visit friends for a special occasion. This will be my go-to place from now on, even though I’m only back every several years!

Tiny home in Belews Creek

5 out of 5 average rating, 13 reviews

Tiny Barnside Escape

BrandyRating, 5 stars2 weeks ago

Chelsea was so sweet and super nice. We went for a ball and she agreed for us to check in early and even put extra mirrors up for us. I would definitely stay here again and stay longer. She always responded fast and was interested in what we had going on. She really felt like a friend! The drive to get there on the gravel path was so nice and very beautiful. I would recommend to anyone! CANT WAIT TO GO BACK!

Cabin in Tobaccoville

5 out of 5 average rating, 4 reviews

Charming Historic Tobacco Barn W/ Modern Amenities

SavannahRating, 5 stars1 month ago

I absolutely loved this little cabin. It felt so cozy and it was adorable. The lights on the outside were beautifully. Absolutely love the hosts. Highly recommend and would stay here again

Guest suite in Ardmore

5 out of 5 average rating, 4 reviews

The Ardmore Hideaway

Mary-DawnRating, 5 stars2 days ago

We traveled into town for an overnight stay for a funeral. Bek was so accommodating and so kind. We would stay here again anytime!

5 out of 5 average rating, 6 reviews

Flat in Winston-Salem

Immerse in Local Culture

AubryRating, 5 stars1 week ago

I have now stayed at Enola’s place twice and it remains one of the best Airbnbs I have booked! The high ceilings, wooden floors, and large windows are a great addition to such a beautiful space. The bed was very comfortable and cozy. The amenities are top notch as well. Most importantly, these are some of the best and most helpful hosts you will encounter. I can’t recommend this place enough.

Private room in Winston-Salem

4.96 out of 5 average rating, 219 reviews

Easy stay. Room #3

AnthonyRating, 5 stars1 month ago

One of the better Airbnbs I’ve stayed at, property was clean and presented well. Bedroom was spacious, clean and comfortable linen with space to sort luggage. host attention to detail with checkin instructions was great. Parking spots right out the front are ideal too, easy to bring luggage in and out. Will stay again when im in the area.

Private room in Winston-Salem

4.96 out of 5 average rating, 292 reviews

Quiet, Spacious Suite with Private Entrance

VeronicaRating, 5 stars1 month ago

The room was just as described. The area was quiet and peaceful. Wesley promptly responded to my messages. Will stay again in the future.