A baseball stadium with a large crowd, a baseball diamond, and city buildings in the background.

Holiday Homes in Winston - Salem

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winston - Salem holiday homes

1. Updated 1BR cottage on private acre+ lot

Updated 1BR cottage on private acre+ lot
Winston-Salem
10.0 out of 10, Exceptional, (31 reviews)
"Lovely and charming place to stay. Really enjoyed my time there."
United States
Dana A.
The price is €108
includes taxes & fees
11 Nov - 12 Nov
Updated 1BR cottage on private acre+ lot

2. Charming house in Washington Park, W-S, NC

Charming house in Washington Park, W-S, NC
Winston-Salem
10.0 out of 10, Exceptional, (1 review)
"Good location. The beds are exceptionally comfortable. Had a small issue with the couch but he came right over to fix it"
Canada
Robert B.
Charming house in Washington Park, W-S, NC

3. Chic 2BR/2BA Near Dining & Shops

Chic 2BR/2BA Near Dining & Shops
Winston-Salem
9.6 out of 10, Exceptional, (17 reviews)
"Clean, well located, good value, comfortable beds."
United States
Jennifer
The price is €230
includes taxes & fees
15 Nov - 16 Nov
Chic 2BR/2BA Near Dining & Shops

4. La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA

La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
Winston-Salem
10.0 out of 10, Exceptional, (3 reviews)
"Quiet area, cozy rooms and good location. Loved staying here!"
United States
Jessica R.
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA

5. 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)
"Wonderful stay! "
United States
Hannah J.
The price is €248
includes taxes & fees
17 Nov - 18 Nov
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

6. Cozy 3BR Home Near Fairgrounds and Downtown

Cozy 3BR Home Near Fairgrounds and Downtown
Winston-Salem
8.0 out of 10, Very good, (1 review)
"Overall, we had a good stay. The home looked exactly like the photos and comfortably accommodated our group during a difficult time with family. The space was clean and met our needs. My only concerns were that the glass panel/door in the shower was missing, which made the bathroom less functional than expected. I also submitted a request to update the reservation to allow up to 5 guests because we had family and friends stopping by while we were grieving, but I never received a response from...
United States
Jayceon
The price is €225
includes taxes & fees
10 Nov - 11 Nov
Cozy 3BR Home Near Fairgrounds and Downtown

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

Cozy 2-bedroom bungalow in lovely Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (45 reviews)
"We had a great time!"
United States
Kara S.
The price is €231
includes taxes & fees
7 Dec - 8 Dec
Cozy 2-bedroom bungalow in lovely Winston-Salem

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

Downtown Charm, 3 Bdr, Near Rest and Bars
Winston-Salem
9.4 out of 10, Exceptional, (30 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.
Downtown Charm, 3 Bdr, Near Rest and Bars

9. 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, (58 reviews)
"Fantasticly cozy as advertised and wonderful!"
United States
Gerald
The price is €254
includes taxes & fees
16 Nov - 17 Nov
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
The price is €308
includes taxes & fees
19 Nov - 20 Nov
Man cave, Office, Soaking tub, & Firepit.

11. Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
9.6 out of 10, Exceptional, (35 reviews)
"In town for work. Was a Great stay. Staying there again this week"
United States
Natalie K.
Quiet, newly renovated. Near everything!

12. King Suite, Fenced Yard & Fast Wi-Fi - Heart of the NC Triad, Kernersville, NC

King Suite, Fenced Yard & Fast Wi-Fi - Heart of the NC Triad, Kernersville, NC
Kernersville
10.0 out of 10, Exceptional, (4 reviews)
"Great property! Has everything you need and more! Will be for sure staying here again in the future!"
United States
John L.
King Suite, Fenced Yard & Fast Wi-Fi - Heart of the NC Triad, Kernersville, NC

13. New Build 3BR by Wake Forest | Pets OK, Sleeps 6

New Build 3BR by Wake Forest | Pets OK, Sleeps 6
Winston-Salem
The price is €272
includes taxes & fees
10 Nov - 11 Nov
New Build 3BR by Wake Forest | Pets OK, Sleeps 6

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

Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Winston-Salem
9.2 out of 10, Wonderful, (22 reviews)
"The host was very accommodating. Would definitely stay again."
United States
AJb b.
The price is €286
includes taxes & fees
10 Nov - 11 Nov
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown

15. 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
9.2 out of 10, Wonderful, (5 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.
The price is €260
includes taxes & fees
10 Nov - 11 Nov
Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!

16. Luxury 3BR Townhome - Sleep 6

Luxury 3BR Townhome - Sleep 6
Winston-Salem
9.2 out of 10, Wonderful, (58 reviews)
"A clean and well-kept place for a stay. The host was communicative but not intrusive, and the check-in and check-out process was smooth. I would stay here again."
United States
Alyssa B.
The price is €248
includes taxes & fees
10 Nov - 11 Nov
Luxury 3BR Townhome - Sleep 6

17. Private Hot Tub Retreat | King Bed | Outdoor Oasis

Private Hot Tub Retreat | King Bed | Outdoor Oasis
Winston-Salem
10.0 out of 10, Exceptional, (1 review)
"Nice place. Very relax. Didn’t realize people stayed upstairs but never heard them. It was a great stay. Very cozy and comfortable"
United States
Karl R.
Private Hot Tub Retreat | King Bed | Outdoor Oasis

18. 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

19. Spacious Historical Home 3 mins from Downtown

Spacious Historical Home 3 mins from Downtown
Winston-Salem
9.0 out of 10, Wonderful, (4 reviews)
"This is an amazing property with multiple bedrooms, bathrooms and beds, we book it annually for its convenience and value"
United States
Arthur B.
Spacious Historical Home 3 mins from Downtown

20. 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, (62 reviews)
"This is a great place. Clean, updated, close to wake Forest U and the host was perfect - highly recommend."
United States
Melissa T.
The price is €255
includes taxes & fees
10 Nov - 11 Nov
La Casita: A Cozy Retreat Near Wake Forest University"
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winston - Salem Hotel Reviews

Find out more about Winston - Salem

Winston - Salem Holiday Homes information

Number of reviews
331
Accommodation
238 Holiday Homes
Lowest Price
€108
Highest Price
€308

Explore a world of travel with Expedia