A cityscape with various buildings, including a prominent skyscraper and several mid-rise structures.

Winston-Salem Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winston-Salem vacation rentals

Exterior

1. Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Winston-Salem
9.2 out of 10, Wonderful, (22 reviews)
"Cozy clean cabin, had trouble staying warm on the cool nights downstairs until we used the space heater. Altogether a very good stay."
United States
Tim W.
The price is AED 459
AED 938 total
includes taxes & fees
23 Sep - 24 Sep
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Property grounds

2. WEST END WHISPER 3 minute walk or drive to Everything. Prime location.

WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
Winston-Salem
9.4 out of 10, Exceptional, (32 reviews)
"The host was very nice and understanding it was great to find a place pet friendly MollyAnn enjoyed her stay. "
United States
Taya S.
The price is AED 331
AED 515 total
includes taxes & fees
30 Sep - 1 Oct
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
Terrace/patio

3. Cozy 2-bedroom bungalow in lovely Winston-Salem

Cozy 2-bedroom bungalow in lovely Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (38 reviews)
"Great place to stay we appreciate it being dog friendly"
United States
Melinda P.
The price is AED 433
AED 880 total
includes taxes & fees
23 Sep - 24 Sep
Cozy 2-bedroom bungalow in lovely Winston-Salem
Business Apartment | Private kitchen | Espresso maker, coffee/tea maker, fridge, microwave

4. The Ardmore Executive Suite

The Ardmore Executive Suite
4.0 star property
Winston-Salem
7.6 out of 10, Good, (5 reviews)
"Place was wonderful. Host was great. No complaints at all."
United States
Jean
The price is AED 204
AED 597 total
includes taxes & fees
24 Sep - 25 Sep
The Ardmore Executive Suite
Outdoor dining

5. La Casita .

La Casita .
Winston-Salem
9.4 out of 10, Exceptional, (13 reviews)
"The location was perfect for what we needed."
United States
Giuliana
The price is AED 281
AED 691 total
includes taxes & fees
23 Sep - 24 Sep
La Casita .
House | Terrace/patio

6. Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
4.0 star property
Winston-Salem
The price is AED 593
AED 1,588 total
includes taxes & fees
27 Sep - 28 Sep
Winston Sleeps 16 - 2 Kitchens Hot Tub
House | Private kitchen | Espresso maker, coffee/tea maker, fridge, microwave

7. King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit
4.5 star property
Winston-Salem
8.6 out of 10, Excellent, (4 reviews)
"Loved this little house and all the attention to detail! Would definitely return."
United States
Brittney N
The price is AED 446
AED 1,055 total
includes taxes & fees
4 Oct - 5 Oct
King Beds Hot Tub Arcade Grill & Firepit
Microwave, oven, stovetop, dishwasher

8. Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!

Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!
Winston-Salem
9.0 out of 10, Wonderful, (13 reviews)
"Great location and very communicative host!"
United States
Claudia M.
The price is AED 551
AED 714 total
includes taxes & fees
23 Sep - 24 Sep
Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!
Dining

9. Downtown Charm, 3 Bdr, Near Rest and Bars

Downtown Charm, 3 Bdr, Near Rest and Bars
Winston-Salem
9.4 out of 10, Exceptional, (27 reviews)
"My husband and I had a wonderful 2-night stay here. The property was incredibly clean and located in a very quiet neighborhood. It was the perfect amount of space for the two of us. We would definitely stay here again!""
United States
Allison T.
The price is AED 525
AED 1,156 total
includes taxes & fees
29 Sep - 30 Sep
Downtown Charm, 3 Bdr, Near Rest and Bars
Coffee/tea maker, fridge, microwave, oven

10. La Casita: A Cozy Retreat Near Wake Forest University"

La Casita: A Cozy Retreat Near Wake Forest University"
Winston-Salem
9.6 out of 10, Exceptional, (60 reviews)
"I enjoyed my stay here. The property was cozy, quiet, clean, and very close to downtown. I was in the area to spend time with family, and was able to host my sister and her two kids with plenty of space. I would definitely stay here again."
United States
Bonnie F.
The price is AED 374
AED 991 total
includes taxes & fees
23 Sep - 24 Sep
La Casita: A Cozy Retreat Near Wake Forest University"
1 bedroom

11. The Hot Tub Hideaway

The Hot Tub Hideaway
Winston-Salem
9.6 out of 10, Exceptional, (37 reviews)
"It was a good stay"
United States
Kim R.
The price is AED 526
AED 905 total
includes taxes & fees
23 Sep - 24 Sep
The Hot Tub Hideaway
Coffee/tea maker, fridge, microwave, oven

12. Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
9.6 out of 10, Exceptional, (33 reviews)
"In town for work. Was a Great stay. Staying there again this week"
United States
Natalie K.
The price is AED 426
AED 967 total
includes taxes & fees
23 Sep - 24 Sep
Quiet, newly renovated. Near everything!
Coffee/tea maker, fridge, microwave, oven

13. New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University

New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
Winston-Salem
10.0 out of 10, Exceptional, (7 reviews)
"We thoroughly enjoyed our stay; very nicely furnished, bed was comfortable and it was very clean and inviting, would not hesitate to rent again in the future"
United States
Catherine D.
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
Exterior

14. 3 Mi to Dtwn Winston-Salem: Studio on Miller Park!

3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
Winston-Salem
9.8 out of 10, Exceptional, (27 reviews)
"What a cute and very clean place to stay! The room is located right at a beautiful park with a walking/running path and wooded trails. Shops are very close by and the neighborhood is cute and safe. Would definitely stay here again. "
United States
Anonymous traveler
The price is AED 242
AED 668 total
includes taxes & fees
28 Sep - 29 Sep
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
Coffee/tea maker, fridge, microwave, oven

15. Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown

Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Winston-Salem
9.4 out of 10, Exceptional, (20 reviews)
"Perfect place for a couple guys for one night stop on our way south for a golf trip. Quick/cheap uber ride to restaurants/town and very clean house!"
United States
Patrick R.
The price is AED 496
AED 1,195 total
includes taxes & fees
23 Sep - 24 Sep
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Coffee/tea maker, fridge, microwave, oven

16. Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore

Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore
Winston-Salem
9.4 out of 10, Exceptional, (13 reviews)
"Host was very friendly - place was super clean and exactly as listed!"
United States
Brittany
The price is AED 422
AED 1,054 total
includes taxes & fees
28 Sep - 29 Sep
Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore
Terrace/patio

17. Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
Winston-Salem
9.6 out of 10, Exceptional, (56 reviews)
"Enjoyable atmosphere, accommodating host, and a beautiful home overall. I’ll definitely plan another booking with them!"
United States
Brian Z.
The price is AED 617
AED 1,029 total
includes taxes & fees
24 Sep - 25 Sep
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
Interior

18. Man cave, Office, Soaking tub, & Firepit.

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
Man cave, Office, Soaking tub, & Firepit.
TV, video games

19. Spacious Historical Home 3 mins from Downtown

Spacious Historical Home 3 mins from Downtown
Winston-Salem
8.8 out of 10, Excellent, (3 reviews)
"I recommend this 👌"
United States
Melvin
Spacious Historical Home 3 mins from Downtown
Terrace/patio

20. Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!

Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!
Winston-Salem
8.0 out of 10, Very good, (2 reviews)
"Overall had good amenities and was nicely renovated and decorated. Disappointed in the initial cleanliness of the unit for the price paid"
United States
Tatiana U.
Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winston-Salem Hotel Reviews

Sleep Inn Hanes Mall

Sleep Inn Hanes Mall

8/10 Good
"I really enjoy my stay. The rooms are nice and clean and the staff are very attentive. This will be my third time staying there."
Florence 1-night trip
Posted 7 hours ago
Sleep Inn Hanes Mall

Frequently asked questions

Can I find vacation rentals in Winston-Salem?

Yes, there are vacation rentals in Winston-Salem close to Salem College Elberson Fine Arts Center, or you can go with a more secluded option if you'd like a relaxing place to stay. Visitors like the array of shops and lush forest in Winston-Salem. Make sure to also enjoy the college campus and top-notch restaurants during your vacation.

What are some of the best vacation rentals that Winston-Salem has to offer?

Arcade Kid Friendly Firepit Grill HotTub: This highly rated vacation home rental in Winston-Salem is located near the airport and has a fireplace, a private balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Other favorite homes for rent in Winston-Salem are Cozy 2-bedroom bungalow in lovely Winston-Salem and Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!.

How many vacation rentals will I find in Winston-Salem?

Choose from 210 Expedia vacation rentals in Winston-Salem for a memorable vacation.

What can I see and do in Winston-Salem?

Enjoy the outdoors at Reynolda Gardens and Salem Lake, or simply take in cultural attractions like Old Salem and Reynolda House Museum of American Art. Truist Stadium and Bowman Gray Stadium are other places to visit while you're in town.

What are vacation rentals like in Winston-Salem?

Vacation rentals are privately owned properties you can book for several days or longer in Winston-Salem. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family gatherings.