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

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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 holiday homes

A kitchen with white cabinets, a granite countertop, a stove, and a microwave. There is a hanging light fixture and a window with blinds.

1. Updated 1BR cottage on private acre+ lot

Updated 1BR cottage on private acre+ lot
Winston-Salem
10.0 out of 10, Exceptional, (29 reviews)
"The cottage was very cozy and clean, and the amenities provided were helpful! It was conveniently located for all the places we had to go and in a quiet neighborhood."
United States
Joanne A.
The price is £105
includes taxes & fees
6 Oct - 7 Oct
Updated 1BR cottage on private acre+ lot
A covered porch with wooden flooring, black chairs, and hanging planters.

2. 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 £183
includes taxes & fees
24 Sept - 25 Sept
Cozy 2-bedroom bungalow in lovely Winston-Salem
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

3. 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 £140
includes taxes & fees
29 Sept - 30 Sept
The Ardmore Executive Suite
A living room with a sectional sofa, a coffee table, and a side table. There are two windows with blinds, a ceiling fan, and a painting of the Eiffel Tower.

4. Cozy home in Ardmore Winston-Salem pet friendly, close to hospital & University

Cozy home in Ardmore Winston-Salem pet friendly, close to hospital & University
Winston-Salem
The price is £163
includes taxes & fees
27 Sept - 28 Sept
Cozy home in Ardmore Winston-Salem pet friendly, close to hospital & University
A rustic wooden cabin with a porch, surrounded by greenery and a tree with pink flowers.

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)
"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 £197
includes taxes & fees
24 Sept - 25 Sept
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
A wooden deck with wicker furniture, a grill, and a white door.

6. Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
4.0 star property
Winston-Salem
The price is £324
includes taxes & fees
29 Sept - 30 Sept
Winston Sleeps 16 - 2 Kitchens Hot Tub
A modern kitchen with white cabinets, a stainless steel refrigerator, and a tiled backsplash.

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 £215
includes taxes & fees
4 Oct - 5 Oct
King Beds Hot Tub Arcade Grill & Firepit

8. 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 £145
includes taxes & fees
28 Sept - 29 Sept
La Casita .
A room with two blue armchairs, a patterned rug, a wooden cabinet, and a large mirror on the wall.

9. 3-BR house in Winston-Salem with easy access to hospitals, colleges and shopping

3-BR house in Winston-Salem with easy access to hospitals, colleges and shopping
Winston-Salem
3-BR house in Winston-Salem with easy access to hospitals, colleges and shopping
A backyard with a fire pit, wicker furniture, a hot tub, and a hammock.

10. 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 £225
includes taxes & fees
24 Sept - 25 Sept
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
A modern kitchen with a wooden dining table, chairs, and a hanging light fixture.

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

Downtown Charm, 3 Bdr, Near Rest and Bars
Winston-Salem
9.4 out of 10, Exceptional, (28 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 £237
includes taxes & fees
29 Sept - 30 Sept
Downtown Charm, 3 Bdr, Near Rest and Bars
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

12. 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 £283
includes taxes & fees
24 Sept - 25 Sept
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
A modern kitchen with white cabinets, a black countertop, and a chandelier.

13. 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 £200
includes taxes & fees
28 Sept - 29 Sept
Quiet, newly renovated. Near everything!
A covered porch with two wicker chairs and a small table, a brick wall, and a view of a street and trees.

14. 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!
A spacious kitchen with a granite countertop, a sink, and a dining area with a long table and chairs.

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

Chic 2BR/2BA Near Dining & Shops
Winston-Salem
9.6 out of 10, Exceptional, (15 reviews)
"Very clean and nice"
United States
Juancarlos
Chic 2BR/2BA Near Dining & Shops
A modern kitchen with white subway tiles, stainless steel appliances, and grey cabinetry.

16. 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.
The price is £155
includes taxes & fees
28 Sept - 29 Sept
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
A modern kitchen with a large island, bar stools, and pendant lighting.

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, (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 £222
includes taxes & fees
28 Sept - 29 Sept
La Casita: A Cozy Retreat Near Wake Forest University"
A spacious living room with a large sectional sofa, a green chair, and a coffee table. A staircase with white railings is visible in the background.

18. 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
The price is £279
includes taxes & fees
29 Sept - 30 Sept
Spacious Historical Home 3 mins from Downtown
A room with a dark wall, a brown leather sofa, a round coffee table, and a large window with curtains.

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
The price is £265
includes taxes & fees
28 Sept - 29 Sept
Man cave, Office, Soaking tub, & Firepit.
A compact kitchen with a stainless steel refrigerator, an oven, and a microwave.

20. 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 £248
includes taxes & fees
27 Sept - 28 Sept
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
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

Hampton Inn & Suites Winston-Salem/University Area, NC

Hampton Inn & Suites Winston-Salem/University Area, NC

10/10 Excellent
"Todo"
Yeison 3-night trip
Posted 2 hours ago
Hampton Inn & Suites Winston-Salem/University Area, NC

Find out more about Winston-Salem

Winston-Salem Holiday Homes information

Number of reviews
316
Accommodation
647 Holiday Homes
Lowest Price
£105
Highest Price
£324