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Our top choices for Winston-Salem holiday homes
1. Updated 1BR cottage on private acre+ lot
Updated 1BR cottage on private acre+ lotWinston-Salem
10.0 out of 10, Exceptional, (31 reviews)
"Lovely and charming place to stay. Really enjoyed my time there."
Dana A.
2. Charming house in Washington Park, W-S, NC
Charming house in Washington Park, W-S, NCWinston-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"
Robert B.
The price is NZ$281
includes taxes & fees
7 Dec - 8 Dec
3. La Casita .
La Casita .Winston-Salem
9.6 out of 10, Exceptional, (18 reviews)
"The location was perfect for what we needed."
Giuliana
The price is NZ$335
includes taxes & fees
8 Dec - 9 Dec
4. Chic 2BR/2BA Near Dining & Shops
Chic 2BR/2BA Near Dining & ShopsWinston-Salem
9.6 out of 10, Exceptional, (17 reviews)
"Clean, well located, good value, comfortable beds."
Jennifer
The price is NZ$455
includes taxes & fees
15 Nov - 16 Nov
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 UNCSAWinston-Salem
9.0 out of 10, Wonderful, (4 reviews)
"Quiet area, cozy rooms and good location. Loved staying here!"
Jessica R.
The price is NZ$346
includes taxes & fees
16 Nov - 17 Nov
6. 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
7. 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! "
Hannah J.
The price is NZ$484
includes taxes & fees
17 Nov - 18 Nov
8. Cozy 2-bedroom bungalow in lovely Winston-Salem
Cozy 2-bedroom bungalow in lovely Winston-SalemWinston-Salem
10.0 out of 10, Exceptional, (45 reviews)
"We had a great time!"
Kara S.
The price is NZ$443
includes taxes & fees
7 Dec - 8 Dec
9. Cozy 3BR Home Near Fairgrounds and Downtown
Cozy 3BR Home Near Fairgrounds and DowntownWinston-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...
Jayceon
The price is NZ$458
includes taxes & fees
16 Nov - 17 Nov
10. La Casita #3
La Casita #3Winston-Salem
The price is NZ$14,718
includes taxes & fees
16 Nov - 17 Nov
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"
Natalie K.
The price is NZ$445
includes taxes & fees
12 Nov - 13 Nov
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!"
Gerald
The price is NZ$490
includes taxes & fees
8 Dec - 9 Dec
13. Luxury 3BR Townhome - Sleep 6
Luxury 3BR Townhome - Sleep 6Winston-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."
Alyssa B.
The price is NZ$524
includes taxes & fees
8 Dec - 9 Dec
14. Downtown Charm, 3 Bdr, Near Rest and Bars
Downtown Charm, 3 Bdr, Near Rest and BarsWinston-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!""
Allison T.
The price is NZ$556
includes taxes & fees
30 Nov - 1 Dec
15. New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest UniversityWinston-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"
Catherine D.
The price is NZ$694
includes taxes & fees
22 Nov - 23 Nov
16. 4 Beds | King | 85” TV | 5min to WSSU & Downtown
4 Beds | King | 85” TV | 5min to WSSU & DowntownWinston-Salem
9.0 out of 10, Wonderful, (4 reviews)
"We enjoyed our short stay, house is very cute and cozy and well put together "
Anonymous traveller
17. 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."
Melissa T.
The price is NZ$488
includes taxes & fees
12 Nov - 13 Nov
18. Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Winston Salem 3Bd 2Ba GAME ROOM mins to DowntownWinston-Salem
9.4 out of 10, Exceptional, (23 reviews)
"The host was very accommodating. Would definitely stay again."
AJb b.
The price is NZ$561
includes taxes & fees
22 Nov - 23 Nov
19. Private Hot Tub Retreat | King Bed | Outdoor Oasis
Private Hot Tub Retreat | King Bed | Outdoor OasisWinston-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"
Karl R.
The price is NZ$647
includes taxes & fees
17 Nov - 18 Nov
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
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"
Tatiana U.
The price is NZ$504
includes taxes & fees
12 Nov - 13 Nov
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.
Learn more about Winston-Salem
Explore Old Salem's living history museum where costumed interpreters demonstrate crafts and daily life from the 1700s. Discover the city's artistic side at Reynolda House, featuring American art within the historic estate of tobacco magnate R.J. Reynolds.
