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

Holiday Homes in Winston-Salem

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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, (30 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 AU$207
includes taxes & fees
26 Oct - 27 Oct
Updated 1BR cottage on private acre+ lot
A modern kitchen with white subway tiles, stainless steel appliances, and grey cabinetry.

2. 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 AU$292
includes taxes & fees
20 Oct - 21 Oct
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
Outdoor dining

3. La Casita .

La Casita .
Winston-Salem
9.4 out of 10, Exceptional, (14 reviews)
"The location was perfect for what we needed."
United States
Giuliana
The price is AU$280
includes taxes & fees
26 Oct - 27 Oct
La Casita .
A covered porch with wooden flooring, black chairs, and hanging planters.

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

Cozy 2-bedroom bungalow in lovely Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (42 reviews)
"Great place to stay we appreciate it being dog friendly"
United States
Melinda P.
The price is AU$348
includes taxes & fees
15 Oct - 16 Oct
Cozy 2-bedroom bungalow in lovely Winston-Salem
A bedroom with a large bed, two bedside tables, a ceiling fan, and a window with curtains.

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
The price is AU$542
includes taxes & fees
26 Oct - 27 Oct
Man cave, Office, Soaking tub, & Firepit.
A spacious kitchen with a granite countertop, a sink, and a dining area with a long table and chairs.

6. 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 rustic wooden cabin with a porch, surrounded by greenery and a tree with pink flowers.

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)
"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 AU$407
includes taxes & fees
20 Oct - 21 Oct
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
A bedroom with a wooden bed, two bedside tables with lamps, a window with blinds, and a wooden floor.

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

Charming house in Washington Park, W-S, NC
Winston-Salem
The price is AU$243
includes taxes & fees
14 Nov - 15 Nov
Charming house in Washington Park, W-S, NC
A modern kitchen with white cabinets, a black countertop, and a chandelier.

9. Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
9.6 out of 10, Exceptional, (34 reviews)
"In town for work. Was a Great stay. Staying there again this week"
United States
Natalie K.
The price is AU$377
includes taxes & fees
19 Oct - 20 Oct
Quiet, newly renovated. Near everything!
A bedroom with a bed, bedside tables, a desk, and a chair. There is a window with curtains, a ceiling fan, and a wall-mounted lamp.

10. Charming 4-bedroom house in Winston-Salem near hospitals, downtown,universities

Charming 4-bedroom house in Winston-Salem near hospitals, downtown,universities
Winston-Salem
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay here! The host was very welcoming and the house was clean and comfortable. Definitely recommend for anyone looking for a stay in the area!"
United States
Jen B.
Charming 4-bedroom house in Winston-Salem near hospitals, downtown,universities
A modern kitchen with white cabinets, a stainless steel refrigerator, and a marble backsplash. There are two bar stools and a wooden dining table with chairs.

11. 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 AU$375
includes taxes & fees
3 Nov - 4 Nov
Cozy 3BR Home Near Fairgrounds and Downtown
A compact kitchen with white cabinets, a stainless steel refrigerator, a dining table with chairs, and a small potted plant.

12. La Casita #3

La Casita #3
Winston-Salem
The price is AU$12,497
includes taxes & fees
26 Oct - 27 Oct
La Casita #3
A modern kitchen with a wooden dining table, chairs, and a hanging light fixture.

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

Downtown Charm, 3 Bdr, Near Rest and Bars
Winston-Salem
9.4 out of 10, Exceptional, (29 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 AU$586
includes taxes & fees
11 Nov - 12 Nov
Downtown Charm, 3 Bdr, Near Rest and Bars
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

14. 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 AU$529
includes taxes & fees
2 Nov - 3 Nov
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
A wooden deck with two blue chairs and a table, surrounded by a wooden railing and dense greenery.

15. 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 AU$445
includes taxes & fees
3 Nov - 4 Nov
Luxury 3BR Townhome - Sleep 6
A modern kitchen with a large island, bar stools, and pendant lighting.

16. 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, (61 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 AU$428
includes taxes & fees
20 Oct - 21 Oct
La Casita: A Cozy Retreat Near Wake Forest University"
A compact kitchen with a stainless steel refrigerator, an oven, and a microwave.

17. 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)
"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 AU$465
includes taxes & fees
21 Oct - 22 Oct
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
A backyard with a fire pit, wicker furniture, a hot tub, and a hammock.

18. 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 AU$423
includes taxes & fees
22 Oct - 23 Oct
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
A covered porch with two wicker chairs and a small table, a brick wall, and a view of a street and trees.

19. 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.
The price is AU$427
includes taxes & fees
19 Oct - 20 Oct
Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!
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.

20. 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
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

Suburban Studios Winston Salem-University Parkway

Suburban Studios Winston Salem-University Parkway

10/10 Excellent
"I choose this site because it was 6.2 miles from the Forsyth Medical Center. I live too far away so I needed a room. It was clean and well cared for. The parking lot is lite up, fully, with LED lighting a night. Handicap parking. Parking in front of the rooms. The room was neat & spotless, no bugs either. There is a small burea, a shelf over it; a table & 2 chairs; nice size refrigerator; 2 coiled areas to cook on a counter with a sink; storage cabinets; full bathroom with out stains; no pealing paint on walls/clean and cared for. The staff are friendly & helpful. They are working on it constantly. The price is correct for a minimalist room. No breakfast, no pool, just a basic room. Great if it’s all you need or want. I would 100% stay there again. I felt safe & thankful."
Marie 1-night trip
Posted 15 hours ago
Suburban Studios Winston Salem-University Parkway

Find out more about Winston-Salem

Winston-Salem Holiday Homes information

Number of reviews
336
Accommodation
671 Holiday Homes
Lowest Price
AU$207
Highest Price
AU$12,497