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 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.
$125 nightly
The price is $142
Oct 22 - Oct 23
Total with taxes and fees
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
9.2 out of 10, Wonderful, (35 reviews)
"Lovely unit convenient to the theatre district and restaurants."
United States
Kelly N.
$133 nightly
The price is $150
Oct 19 - Oct 20
Total with taxes and fees
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.

3. 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
$161 nightly
The price is $182
Oct 18 - Oct 19
Total with taxes and fees
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
Outdoor dining

4. 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
$170 nightly
The price is $192
Oct 20 - Oct 21
Total with taxes and fees
La Casita .
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, (43 reviews)
"Great place to stay we appreciate it being dog friendly"
United States
Melinda P.
$214 nightly
The price is $242
Oct 20 - Oct 21
Total with taxes and fees
Cozy 2-bedroom bungalow in lovely Winston-Salem
A modern kitchen with white subway tiles, stainless steel appliances, and grey cabinetry.

6. 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.
$182 nightly
The price is $206
Oct 20 - Oct 21
Total with taxes and fees
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
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
9.6 out of 10, Exceptional, (15 reviews)
"Very clean and nice"
United States
Juancarlos
$252 nightly
The price is $268
Nov 3 - Nov 4
Total with taxes and fees
Chic 2BR/2BA Near Dining & Shops
A rustic wooden cabin with a porch, surrounded by greenery and a tree with pink flowers.

8. 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.
$254 nightly
The price is $287
Oct 20 - Oct 21
Total with taxes and fees
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
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.

9. 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
$245 nightly
The price is $262
Nov 2 - Nov 3
Total with taxes and fees
Cozy 3BR Home Near Fairgrounds and Downtown
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, (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.
$292 nightly
The price is $313
Nov 3 - Nov 4
Total with taxes and fees
Downtown Charm, 3 Bdr, Near Rest and Bars
A modern kitchen with white cabinets, a black countertop, and a chandelier.

11. 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.
$234 nightly
The price is $264
Oct 19 - Oct 20
Total with taxes and fees
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.

12. 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.
$404 nightly
The price is $457
Oct 23 - Oct 24
Total with taxes and fees
Charming 4-bedroom house in Winston-Salem near hospitals, downtown,universities
A bathroom with a blue wall, a white sink, a mirror with a gold frame, a wooden floor, and a patterned rug.

13. 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
$72 nightly
The price is $81
Nov 2 - Nov 3
Total with taxes and fees
Kernersville NC|King Bed
A bedroom with a large bed, two bedside tables, a ceiling fan, and a window with curtains.

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
$341 nightly
The price is $385
Oct 26 - Oct 27
Total with taxes and fees
Man cave, Office, Soaking tub, & Firepit.
A small cabin surrounded by trees with a gravel path leading to it.

15. The Red Door Cabin

The Red Door Cabin
Winston-Salem
10.0 out of 10, Exceptional, (28 reviews)
"Cute place. "
United States
Sue C.
$238 nightly
The price is $269
Oct 26 - Oct 27
Total with taxes and fees
The Red Door Cabin
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

16. 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.
$333 nightly
The price is $376
Oct 20 - Oct 21
Total with taxes and fees
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden dining table.

17. 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
$257 nightly
The price is $290
Nov 2 - Nov 3
Total with taxes and fees
Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore
A bedroom with a large window overlooking a forest. There is a bed with pillows and a wooden headboard.

18. The Hot Tub Hideaway

The Hot Tub Hideaway
Winston-Salem
9.6 out of 10, Exceptional, (38 reviews)
"What a beautiful cabin tucked away off the road. You’ll think you’re driving into a scary movie but then it opens up to the most beautiful view. Truly sleeping under the stars. Very clean cabin, would 100% stay again."
United States
Alyse P.
$238 nightly
The price is $269
Oct 20 - Oct 21
Total with taxes and fees
The Hot Tub Hideaway
A modern kitchen with a large island, bar stools, and pendant lighting.

19. 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.
$265 nightly
The price is $299
Nov 3 - Nov 4
Total with taxes and fees
La Casita: A Cozy Retreat Near Wake Forest University"
A covered porch with two wicker chairs and a small table, a brick wall, and a view of a street and trees.

20. 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.
$265 nightly
The price is $300
Oct 19 - Oct 20
Total with taxes and fees
Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!
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

Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

10/10 Excellent
"The hotel was clean and well kept. The staff professional & welcoming."
Michelle 2-night trip
Posted 1 hour ago
Hawthorne Inn and Conference Center

Find out more about Winston - Salem

Everything you need to know about Winston - Salem vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winston - Salem vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

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Winston - Salem vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winston - Salem. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winston - Salem in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $81 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winston - Salem rentals

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