A baseball stadium with a large crowd, a baseball diamond, and city buildings in the background.

Winston - Salem Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winston - Salem holiday rentals

A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

1. 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$770
HK$1,655 total
includes taxes & fees
5 Oct - 6 Oct
The Ardmore Executive Suite
A kitchen with white cabinets, a granite countertop, a stove, and a microwave. There is a hanging light fixture and a window with blinds.

2. 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$398
HK$1,044 total
includes taxes & fees
6 Oct - 7 Oct
Updated 1BR cottage on private acre+ lot
A modern kitchen with white cabinets, a stainless steel dishwasher, and a granite countertop.

3. 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, (33 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
8 Oct - 9 Oct
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
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$518
HK$1,428 total
includes taxes & fees
13 Oct - 14 Oct
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
Outdoor dining

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

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)
"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$968
HK$2,237 total
includes taxes & fees
13 Oct - 14 Oct
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.

7. 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$2,815 total
includes taxes & fees
12 Oct - 13 Oct
Winston Sleeps 16 - 2 Kitchens Hot Tub
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.

8. 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 HK$777
HK$2,033 total
includes taxes & fees
4 Nov - 5 Nov
Cozy 3BR Home Near Fairgrounds and Downtown
A spacious kitchen with a granite countertop, a sink, and a dining area with a long table and chairs.

9. 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
The price is HK$2,068
HK$3,736 total
includes taxes & fees
18 Oct - 19 Oct
Chic 2BR/2BA Near Dining & Shops
A living room with a television, leather sofas, a coffee table, a potted plant, and a chandelier.

10. 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
4 Beds | King | 85” TV | 5min to WSSU & Downtown
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 modern kitchen with white cabinets, a black countertop, and a chandelier.

12. 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 HK$910
HK$2,066 total
includes taxes & fees
5 Oct - 6 Oct
Quiet, newly renovated. Near everything!
A covered porch with wooden flooring, black chairs, and hanging planters.

13. 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$1,879 total
includes taxes & fees
13 Oct - 14 Oct
Cozy 2-bedroom bungalow in lovely Winston-Salem
A bedroom with a large window overlooking a forest. There is a bed with pillows and a wooden headboard.

14. 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$1,248
HK$2,093 total
includes taxes & fees
8 Oct - 9 Oct
The Hot Tub Hideaway
A modern kitchen with a wooden dining table, chairs, and a hanging light fixture.

15. 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.
Downtown Charm, 3 Bdr, Near Rest and Bars
A modern kitchen with white cabinets, stainless steel appliances, and wooden shelves.

16. Stylish 1BR Near Downtown & WFU Hospital

Stylish 1BR Near Downtown & WFU Hospital
Winston Salem
10.0 out of 10, Exceptional, (7 reviews)
"My husband stayed here for one month during an away rotation for medical school and had a wonderful experience! It’s walkable to the hospital, safe, charming, clean, stocked with all of the essentials, and the property managers are very responsive and even proactive in making the stay positive. Highly recommend!!"
United States
Anonymous traveller
The price is HK$1,562
HK$1,995 total
includes taxes & fees
10 Oct - 11 Oct
Stylish 1BR Near Downtown & WFU Hospital
A kitchen with wooden cabinets, a microwave, a coffee maker, and a small island with stools.

17. Quit, Cozy, Pet Friendly Condo

Quit, Cozy, Pet Friendly Condo
Winston-Salem
7.8 out of 10, Good, (8 reviews)
"It was sufficient for our short term lodging needs."
United States
Stephanie
Quit, Cozy, Pet Friendly Condo
A modern kitchen with white cabinets, a stainless steel refrigerator, and a tiled backsplash.

18. 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$953
HK$2,255 total
includes taxes & fees
5 Oct - 6 Oct
King Beds Hot Tub Arcade Grill & Firepit
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

19. 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.
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
A bedroom with a large bed, two bedside tables, a ceiling fan, and a window with curtains.

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
The price is HK$942
HK$2,980 total
includes taxes & fees
6 Oct - 7 Oct
Man cave, Office, Soaking tub, & Firepit.
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
"Centrally located in Downtown Winston-Salem, within walking distance of good restaurants. The room was clean, with good breakfast selections and convenient on-site valet."
David 3-night trip
Posted 2 days ago
Hampton Inn & Suites Winston-Salem Downtown

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