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Winston - Salem Holiday Rentals

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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 rentals

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 HK$313
HK$948 total
includes taxes & fees
30 Sept - 1 Oct
Updated 1BR cottage on private acre+ lot
A modern kitchen with white cabinets, a stainless steel dishwasher, and a granite countertop.

2. WEST END WHISPER 3 minute walk or drive to Everything. Prime location.

WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
Winston-Salem
9.4 out of 10, Exceptional, (32 reviews)
"The host was very nice and understanding it was great to find a place pet friendly MollyAnn enjoyed her stay. "
United States
Taya S.
The price is HK$706
HK$1,179 total
includes taxes & fees
30 Sept - 1 Oct
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.

3. 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
La Casita .
A yellow house with a red door, a brick chimney, and a front yard with small bushes.

4. 3 Mi to Dtwn Winston-Salem: Studio on Miller Park!

3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
Winston-Salem
9.8 out of 10, Exceptional, (27 reviews)
"What a cute and very clean place to stay! The room is located right at a beautiful park with a walking/running path and wooded trails. Shops are very close by and the neighborhood is cute and safe. Would definitely stay here again. "
United States
Anonymous traveller
The price is HK$557
HK$1,471 total
includes taxes & fees
13 Oct - 14 Oct
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
A covered porch with wooden flooring, black chairs, and hanging planters.

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

Cozy 2-bedroom bungalow in lovely Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (39 reviews)
"Great place to stay we appreciate it being dog friendly"
United States
Melinda P.
The price is HK$925
HK$1,843 total
includes taxes & fees
30 Sept - 1 Oct
Cozy 2-bedroom bungalow in lovely Winston-Salem
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

6. 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 HK$549
HK$1,405 total
includes taxes & fees
29 Sept - 30 Sept
The Ardmore Executive Suite
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 HK$981
HK$2,172 total
includes taxes & fees
30 Sept - 1 Oct
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
A modern kitchen with white cabinets, a black countertop, and a chandelier.

8. 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 HK$910
HK$2,003 total
includes taxes & fees
28 Sept - 29 Sept
Quiet, newly renovated. Near everything!
A bedroom with a bed, bedside lamps, a chair, an ottoman, a window with curtains, an air conditioning unit, and a mirror on the wall.

9. Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem

Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem
Winston Salem
10.0 out of 10, Exceptional, (2 reviews)
"Great stay wonderful experience"
United States
dillon b.
The price is HK$557
HK$1,471 total
includes taxes & fees
28 Sept - 29 Sept
Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem
A modern kitchen with a wooden dining table, chairs, and a hanging light fixture.

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, (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.
Downtown Charm, 3 Bdr, Near Rest and Bars
A modern kitchen with white subway tiles, stainless steel appliances, and grey cabinetry.

11. 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
A bedroom with a large window overlooking a forest. There is a bed with pillows and a wooden headboard.

12. The Hot Tub Hideaway

The Hot Tub Hideaway
Winston-Salem
9.6 out of 10, Exceptional, (37 reviews)
"It was a good stay"
United States
Kim R.
The price is HK$1,247
HK$2,030 total
includes taxes & fees
29 Sept - 30 Sept
The Hot Tub Hideaway
A modern kitchen with white cabinets, a stainless steel refrigerator, and a tiled backsplash.

13. 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 HK$915
HK$2,210 total
includes taxes & fees
28 Sept - 29 Sept
King Beds Hot Tub Arcade Grill & Firepit
A kitchen with white cabinets, a stainless steel refrigerator, a black stove, and a trash bin.

14. 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
Cozy home in Ardmore Winston-Salem pet friendly, close to hospital & University
A house with a brick exterior, a white door, and a number '6606' on the wall.

15. Cozy 1-bedroom in lovely Downtown Lewisville: The Charleston

Cozy 1-bedroom in lovely Downtown Lewisville: The Charleston
Lewisville
9.6 out of 10, Exceptional, (4 reviews)
"This location is ideal in Lewisville. Quite and safe area. Within walking distance to parks, grocery stores and restaurants. The hosts are fantastic - very responsive and helpful. The home is very clean and has everything you would need for your stay."
United States
Cheryl G.
The price is HK$563
HK$813 total
includes taxes & fees
28 Sept - 29 Sept
Cozy 1-bedroom in lovely Downtown Lewisville: The Charleston
A wooden deck with wicker furniture, a grill, and a white door.

16. Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
4.0 star property
Winston-Salem
The price is HK$755
HK$2,814 total
includes taxes & fees
28 Oct - 29 Oct
Winston Sleeps 16 - 2 Kitchens Hot Tub
A small cabin surrounded by trees with a gravel path leading to it.

17. The Red Door Cabin

The Red Door Cabin
Winston-Salem
10.0 out of 10, Exceptional, (24 reviews)
"Cute place. "
United States
Sue C.
The price is HK$1,122
HK$1,889 total
includes taxes & fees
28 Sept - 29 Sept
The Red Door Cabin
A modern kitchen with a large island, bar stools, and pendant lighting.

18. 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)
"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 HK$918
HK$2,189 total
includes taxes & fees
28 Sept - 29 Sept
La Casita: A Cozy Retreat Near Wake Forest University"
A bedroom with a large bed, two bedside tables, a ceiling fan, and a window with curtains.

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
Man cave, Office, Soaking tub, & Firepit.
A compact kitchen with white cabinets, a stainless steel refrigerator, a dining table with chairs, and a small potted plant.

20. La Casita #3

La Casita #3
Winston-Salem
The price is HK$649
HK$66,848 total
includes taxes & fees
28 Sept - 29 Sept
La Casita #3
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 Downtown

Hampton Inn & Suites Winston-Salem Downtown

10/10 Excellent
"Great breakfast, very helpful valet, clean rooms, great location"
Keith 2-night trip
Posted 5 hours ago
Hampton Inn & Suites Winston-Salem Downtown

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