Photo by Visit Winston Salem

Holiday Homes in Winston - Salem

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Check prices for these dates

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 NZ$274
includes taxes & fees
22 Nov - 23 Nov
Updated 1BR cottage on private acre+ lot

2. La Casita .

La Casita .
Winston-Salem
9.6 out of 10, Exceptional, (18 reviews)
"The location was perfect for what we needed."
United States
Giuliana
The price is NZ$339
includes taxes & fees
8 Dec - 9 Dec
La Casita .

3. 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.
The price is NZ$282
includes taxes & fees
15 Nov - 16 Nov
Charming house in Washington Park, W-S, NC

4. 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 NZ$455
includes taxes & fees
15 Nov - 16 Nov
Chic 2BR/2BA Near Dining & Shops

5. 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
9.0 out of 10, Wonderful, (4 reviews)
"Quiet area, cozy rooms and good location. Loved staying here!"
United States
Jessica R.
The price is NZ$359
includes taxes & fees
17 Nov - 18 Nov
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA

6. 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 NZ$490
includes taxes & fees
17 Nov - 18 Nov
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

7. 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 NZ$458
includes taxes & fees
16 Nov - 17 Nov
Cozy 3BR Home Near Fairgrounds and Downtown

8. 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 NZ$415
includes taxes & fees
15 Nov - 16 Nov
Cozy 2-bedroom bungalow in lovely Winston-Salem

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
The price is NZ$623
includes taxes & fees
19 Nov - 20 Nov
Man cave, Office, Soaking tub, & Firepit.

10. 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.
The price is NZ$563
includes taxes & fees
7 Dec - 8 Dec
Downtown Charm, 3 Bdr, Near Rest and Bars

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.
The price is NZ$445
includes taxes & fees
15 Nov - 16 Nov
Quiet, newly renovated. Near everything!

12. 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 NZ$476
includes taxes & fees
16 Nov - 17 Nov
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

13. 4 Beds | King | 85” TV | 5min to WSSU & Downtown

4 Beds | King | 85” TV | 5min to WSSU & Downtown
Winston-Salem
9.0 out of 10, Wonderful, (4 reviews)
"We enjoyed our short stay, house is very cute and cozy and well put together "
United States
Anonymous traveller
The price is NZ$426
includes taxes & fees
15 Nov - 16 Nov
4 Beds | King | 85” TV | 5min to WSSU & Downtown

14. 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.
The price is NZ$404
includes taxes & fees
29 Nov - 30 Nov
King Suite, Fenced Yard & Fast Wi-Fi - Heart of the NC Triad, Kernersville, NC

15. 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.
The price is NZ$694
includes taxes & fees
22 Nov - 23 Nov
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University

16. 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 NZ$504
includes taxes & fees
15 Nov - 16 Nov
Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!

17. 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, (24 reviews)
"The host was very accommodating. Would definitely stay again."
United States
AJb b.
The price is NZ$561
includes taxes & fees
22 Nov - 23 Nov
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown

18. 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.
The price is NZ$655
includes taxes & fees
17 Nov - 18 Nov
Private Hot Tub Retreat | King Bed | Outdoor Oasis

19. 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, (63 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 NZ$482
includes taxes & fees
16 Nov - 17 Nov
La Casita: A Cozy Retreat Near Wake Forest University"

20. Luxury 3BR Townhome - Sleep 6

Luxury 3BR Townhome - Sleep 6
Winston-Salem
9.2 out of 10, Wonderful, (59 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 NZ$522
includes taxes & fees
8 Dec - 9 Dec
Luxury 3BR Townhome - Sleep 6
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.

Winston - Salem and related destinations

Old Salem's living history museum brings the 1700s to life, while art lovers flock to Reynolda House for American masterpieces. Foodies shouldn't miss sampling local craft beers and Southern comfort dishes in the city centre Arts District.

A cityscape at dusk with prominent buildings like the Winston Tower and a modern skyscraper.
Photo by Visit Winston Salem
Open Photo by Visit Winston Salem

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