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

Winston - Salem Vacation Rentals

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Check prices for these dates

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

Our top choices for Winston - Salem vacation rentals

A modern kitchen with white cabinets, a stainless steel dishwasher, and a granite countertop.

1. 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
9.2 out of 10, Wonderful, (35 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 ￥14,248
￥23,793 total
includes taxes & fees
Oct 19 - Oct 20
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
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, (42 reviews)
"Great place to stay we appreciate it being dog friendly"
United States
Melinda P.
The price is ￥18,665
￥38,267 total
includes taxes & fees
Oct 14 - Oct 15
Cozy 2-bedroom bungalow in lovely Winston-Salem
A kitchen with white cabinets, a granite countertop, a stove, and a microwave. There is a hanging light fixture and a window with blinds.

3. 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 ￥10,771
￥24,156 total
includes taxes & fees
Oct 22 - Oct 23
Updated 1BR cottage on private acre+ lot
A modern kitchen with white subway tiles, stainless steel appliances, and grey cabinetry.

4. 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 ￥13,536
￥31,756 total
includes taxes & fees
Oct 26 - Oct 27
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
Outdoor dining

5. 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 ￥13,108
￥31,092 total
includes taxes & fees
Oct 20 - Oct 21
La Casita .
A modern kitchen with a wooden dining table, chairs, and a hanging light fixture.

6. 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 ￥20,897
￥47,875 total
includes taxes & fees
Nov 3 - Nov 4
Downtown Charm, 3 Bdr, Near Rest and Bars
A yellow house with a red door, a brick chimney, and a front yard with small bushes.

7. 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 traveler
The price is ￥10,448
￥28,801 total
includes taxes & fees
Oct 22 - Oct 23
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
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, (34 reviews)
"In town for work. Was a Great stay. Staying there again this week"
United States
Natalie K.
The price is ￥18,364
￥41,683 total
includes taxes & fees
Oct 14 - Oct 15
Quiet, newly renovated. Near everything!
A rustic wooden cabin with a porch, surrounded by greenery and a tree with pink flowers.

9. 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 ￥19,520
￥45,492 total
includes taxes & fees
Oct 20 - Oct 21
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
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.
The price is ￥24,221
￥72,271 total
includes taxes & fees
Oct 25 - Oct 26
Charming 4-bedroom house in Winston-Salem near hospitals, downtown,universities
A spacious kitchen with a granite countertop, a sink, and a dining area with a long table and chairs.

11. 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 ￥22,440
￥51,341 total
includes taxes & fees
Nov 11 - Nov 12
Chic 2BR/2BA Near Dining & Shops
A bathroom with a blue wall, a white sink, a mirror with a gold frame, a wooden floor, and a patterned rug.

12. Kernersville NC|King Bed

Kernersville NC|King Bed
Kernersville NC
10.0 out of 10, Exceptional, (55 reviews)
"Great location near local attractions made things easy for us as tourists, will keep this place in mind next time!"
United States
Anonymous traveler
The price is ￥10,345
￥12,769 total
includes taxes & fees
Nov 2 - Nov 3
Kernersville NC|King Bed
A bedroom with a bed, two leather chairs, a ceiling fan, and large windows with a view of a fenced yard.

13. Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade
4.5 star property
Winston-Salem
8.0 out of 10, Very good, (1 review)
"The house was very clean, comfortable, and nicely maintained, which we really appreciated during our stay. However, there were two downsides to be aware of. First, after booking, the owner asked us to pay an extra money for cleaning fee, even though it was not clearly listed in the Expedia booking details. I chose not to argue since I didn’t want to ruin our family trip, but future guests should expect additional charges. Second, privacy was an issue the owner lives in the basement, and it felt...
United States
Rami
Heated Pool King Bed Jacuzzi Bath Arcade
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 ￥24,221
￥59,929 total
includes taxes & fees
Nov 2 - Nov 3
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
A compact kitchen with a stainless steel refrigerator, an oven, and a microwave.

15. 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 ￥21,372
￥51,878 total
includes taxes & fees
Oct 14 - Oct 15
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
A covered porch with two wicker chairs and a small table, a brick wall, and a view of a street and trees.

16. 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 ￥21,229
￥47,423 total
includes taxes & fees
Oct 18 - Oct 19
Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!
A wooden deck with wicker furniture, a grill, and a white door.

17. Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
4.0 star property
Winston-Salem
Winston Sleeps 16 - 2 Kitchens Hot Tub
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden dining table.

18. Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore

Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore
Winston-Salem
9.6 out of 10, Exceptional, (14 reviews)
"Host was very friendly - place was super clean and exactly as listed!"
United States
Brittany
The price is ￥18,206
￥45,975 total
includes taxes & fees
Nov 2 - Nov 3
Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore
A single-story house with a black exterior, white trim, and a red roof.

19. 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 traveler
4 Beds | King | 85” TV | 5min to WSSU & Downtown
A wooden deck with two blue chairs and a table, surrounded by a wooden railing and dense greenery.

20. 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 ￥21,245
￥50,520 total
includes taxes & fees
Nov 3 - Nov 4
Luxury 3BR Townhome - Sleep 6
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

Best Western Kernersville

Best Western Kernersville

8/10 Good
"I had reserved a room with a whirlpool’ tub but the jets didn’t work and no one bothered to tell me that or adjust my bill."
Gwendolyn 1-night trip
Posted 3 hours ago
Best Western Kernersville

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