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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winston - Salem vacation 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, (28 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 ￥9,122
￥22,373 total
includes taxes & fees
Sep 9 - Sep 10
Updated 1BR cottage on private acre+ lot
A residential area with a bicycle parked on a concrete path, surrounded by greenery and houses.

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, (30 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 ￥14,334
￥23,936 total
includes taxes & fees
Sep 23 - Sep 24
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
A covered porch with wooden flooring, black chairs, and hanging planters.

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

Cozy 2-bedroom bungalow in lovely Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (35 reviews)
"Great place to stay we appreciate it being dog friendly"
United States
Melinda P.
The price is ￥18,778
￥38,499 total
includes taxes & fees
Aug 29 - Aug 30
Cozy 2-bedroom bungalow in lovely Winston-Salem

4. 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 ￥12,184
￥30,146 total
includes taxes & fees
Sep 2 - Sep 3
La Casita .
A bathroom with a white marble wall and floor, a black hexagonal tile backsplash, and a built-in shelf with toiletries.

5. Exec Suite King Bed Hot Tub Gym Laundry

Exec Suite King Bed Hot Tub Gym Laundry
4.5 star property
Kernersville
4.0 out of 10, (1 review)
"Very nice setup, but wasn't aware that it was a basement that was converted into a studio apartment! Bathroom is extremely small, but shower can fit two! Ceiling in the shower was unfinished, which exposed tubing and insulation!!! Terrible!! Toilet is so close to the wall that it is a struggle to use it!! Hot tub downstairs, which I assume is for basement renters, was completely disgusting!!! My wife and I were lucky to be able to use the one upstairs, only because no one hadn't shown up yet!!!...
United States
Charles
The price is ￥10,482
￥23,789 total
includes taxes & fees
Sep 2 - Sep 3
Exec Suite King Bed Hot Tub Gym Laundry
A yellow house with a red door, a brick chimney, and a front yard with small bushes.

6. 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, (26 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 ￥10,512
￥29,156 total
includes taxes & fees
Aug 31 - Sep 1
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
A spacious kitchen with a granite countertop, a sink, and a dining area with a long table and chairs.

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

Chic 2BR/2BA Near Dining & Shops
Winston-Salem
9.4 out of 10, Exceptional, (13 reviews)
"Very clean and nice"
United States
Juancarlos
The price is ￥16,723
￥44,649 total
includes taxes & fees
Sep 23 - Sep 24
Chic 2BR/2BA Near Dining & Shops
A hotel room with a bed, a TV, a desk, and a chair.

8. Kernersville NC|King Bed

Kernersville NC|King Bed
Kernersville NC
10.0 out of 10, Exceptional, (55 reviews)
"Felt right at home with such a welcoming atmosphere all around us during our stay here."
United States
Anonymous traveler
The price is ￥6,285
￥8,232 total
includes taxes & fees
Sep 23 - Sep 24
Kernersville NC|King Bed
A bedroom with a large window overlooking a forest. There is a bed with pillows and a wooden headboard.

9. 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 ￥22,804
￥39,634 total
includes taxes & fees
Aug 29 - Aug 30
The Hot Tub Hideaway
A bedroom with a bed, two leather chairs, a ceiling fan, and large windows with a view of a fenced yard.

10. 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
The price is ￥28,192
￥71,696 total
includes taxes & fees
Aug 30 - Aug 31
Heated Pool King Bed Jacuzzi Bath Arcade
A rustic wooden cabin with a porch, surrounded by greenery and a tree with pink flowers.

11. 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
9.6 out of 10, Exceptional, (21 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 ￥19,909
￥41,215 total
includes taxes & fees
Sep 2 - Sep 3
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
A modern kitchen with a large island, bar stools, and pendant lighting.

12. 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, (59 reviews)
"Perfect for our family of 3 visiting WFU"
United States
Peter F.
The price is ￥17,848
￥45,741 total
includes taxes & fees
Aug 31 - Sep 1
La Casita: A Cozy Retreat Near Wake Forest University"
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.

13. 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, (1 review)
"The room is clean, quiet, and cozy. I could tell my hosts had thought very carefully about what a guest may need, and they covered all those bases and more. Located in a quiet neighborhood very close to restaurants, grocery stores, etc."
United States
William L.
The price is ￥11,315
￥29,895 total
includes taxes & fees
Aug 29 - Aug 30
Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem
A modern kitchen with a wooden dining table, chairs, and a hanging light fixture.

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

Downtown Charm, 3 Bdr, Near Rest and Bars
Winston-Salem
9.4 out of 10, Exceptional, (25 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 ￥20,673
￥49,569 total
includes taxes & fees
Sep 23 - Sep 24
Downtown Charm, 3 Bdr, Near Rest and Bars
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden dining table.

15. 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, (12 reviews)
"Host was very friendly - place was super clean and exactly as listed!"
United States
Brittany
The price is ￥19,123
￥47,362 total
includes taxes & fees
Sep 7 - Sep 8
Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore
A kitchen with a white bar counter, wooden cabinets, a coffee maker, and a decorative plate on the wall.

16. Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!

Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!
Winston-Salem
9.0 out of 10, Wonderful, (12 reviews)
"Great location and very communicative host!"
United States
Claudia M.
The price is ￥23,891
￥30,959 total
includes taxes & fees
Sep 23 - Sep 24
Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!
A modern kitchen with white subway tiles, stainless steel appliances, and grey cabinetry.

17. 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, (2 reviews)
"Quiet area, cozy rooms and good location. Loved staying here!"
United States
Jessica R.
The price is ￥14,764
￥33,601 total
includes taxes & fees
Sep 2 - Sep 3
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
A bedroom with a bed, a ceiling fan, a nightstand, and wall art.

18. Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds

Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds
Winston-Salem
9.4 out of 10, Exceptional, (3 reviews)
"Great place, definitely an excellent stay."
United States
Ralph S.
The price is ￥15,131
￥40,213 total
includes taxes & fees
Sep 23 - Sep 24
Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds
A small cabin surrounded by trees with a gravel path leading to it.

19. 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 ￥22,804
￥39,814 total
includes taxes & fees
Aug 30 - Aug 31
The Red Door Cabin
A living room with a wooden floor, a ceiling fan, a TV on a stand, a sofa, a coffee table, and a window with patterned curtains.

20. Quaint 2 bed 1 bath cottage style home

Quaint 2 bed 1 bath cottage style home
Kernersville
9.0 out of 10, Wonderful, (50 reviews)
"Enjoyed our visit!"
United States
Andrew
The price is ￥14,191
￥33,853 total
includes taxes & fees
Sep 1 - Sep 2
Quaint 2 bed 1 bath cottage style home
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
"staff was very helpful and attentive"
tripp 2-night trip
Posted 2 hours ago
Hampton Inn & Suites Winston-Salem Downtown

Find out more about Winston - Salem

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