Winston-Salem Vacation Rentals

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Check prices for these dates

Our top choices for Winston-Salem vacation rentals

1. Updated 1BR cottage on private acre+ lot

Updated 1BR cottage on private acre+ lot
Winston-Salem
10.0 out of 10, Exceptional, (31 reviews)
"Lovely and charming place to stay. Really enjoyed my time there."
United States
Dana A.
The price is AEDĀ 216
AEDĀ 455 total
includes taxes & fees
11 Nov - 12 Nov
Updated 1BR cottage on private acre+ lot

2. Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
Winston-Salem
9.6 out of 10, Exceptional, (57 reviews)
"Fantasticly cozy as advertised and wonderful!"
United States
Gerald
The price is AEDĀ 617
AEDĀ 992 total
includes taxes & fees
8 Nov - 9 Nov
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

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, (28 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 AEDĀ 305
AEDĀ 710 total
includes taxes & fees
8 Dec - 9 Dec
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!

4. 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, (37 reviews)
"Property was amazing, clean, and well priced."
United States
Jayden J.
The price is AEDĀ 397
AEDĀ 726 total
includes taxes & fees
8 Nov - 9 Nov
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.

5. 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 AEDĀ 383
AEDĀ 786 total
includes taxes & fees
12 Nov - 13 Nov
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA

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

Cozy 2-bedroom bungalow in lovely Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (45 reviews)
"We had a great time!"
United States
Kara S.
The price is AEDĀ 433
AEDĀ 863 total
includes taxes & fees
8 Nov - 9 Nov
Cozy 2-bedroom bungalow in lovely Winston-Salem

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

Chic 2BR/2BA Near Dining & Shops
Winston-Salem
9.6 out of 10, Exceptional, (17 reviews)
"Clean, well located, good value, comfortable beds."
United States
Jennifer
The price is AEDĀ 347
AEDĀ 932 total
includes taxes & fees
15 Nov - 16 Nov
Chic 2BR/2BA Near Dining & Shops

8. La Casita #3

La Casita #3
Winston-Salem
The price is AEDĀ 301
AEDĀ 31,900 total
includes taxes & fees
10 Nov - 11 Nov
La Casita #3

9. New Build 3BR by Wake Forest | Pets OK, Sleeps 6

New Build 3BR by Wake Forest | Pets OK, Sleeps 6
Winston-Salem
The price is AEDĀ 385
AEDĀ 1,149 total
includes taxes & fees
8 Dec - 9 Dec
New Build 3BR by Wake Forest | Pets OK, Sleeps 6

10. The Hot Tub Hideaway

The Hot Tub Hideaway
Winston-Salem
9.6 out of 10, Exceptional, (38 reviews)
"This place is beautiful! Truly a hidden gem! Perfect little get away for a couple. Spent a 3 day weekend with my bf and dog and it couldn’t have been more peaceful! Shared the listing for this vrbo with multiple friends and family because of how much I loved my stay. Will definitely book again."
United States
Alexandra M.
The price is AEDĀ 584
AEDĀ 942 total
includes taxes & fees
12 Nov - 13 Nov
The Hot Tub Hideaway

11. Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
9.6 out of 10, Exceptional, (35 reviews)
"In town for work. Was a Great stay. Staying there again this week"
United States
Natalie K.
The price is AEDĀ 426
AEDĀ 897 total
includes taxes & fees
8 Nov - 9 Nov
Quiet, newly renovated. Near everything!

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
The price is AEDĀ 422
AEDĀ 1,249 total
includes taxes & fees
19 Nov - 20 Nov
Man cave, Office, Soaking tub, & Firepit.

13. The Red Door Cabin

The Red Door Cabin
Winston-Salem
10.0 out of 10, Exceptional, (29 reviews)
"Cute place. "
United States
Sue C.
The price is AEDĀ 526
AEDĀ 839 total
includes taxes & fees
8 Nov - 9 Nov
The Red Door Cabin

14. Log Cabin on Main St. In the ā¤ļø of Winston Salem. Sleeps 4 comfortably.

Log Cabin on Main St. In the ā¤ļø of Winston Salem. Sleeps 4 comfortably.
Winston-Salem
9.2 out of 10, Wonderful, (22 reviews)
"Wonderful stay! "
United States
Hannah J.
The price is AEDĀ 503
AEDĀ 1,067 total
includes taxes & fees
25 Nov - 26 Nov
Log Cabin on Main St. In the ā¤ļø of Winston Salem. Sleeps 4 comfortably.

15. 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, (62 reviews)
"This is a great place. Clean, updated, close to wake Forest U and the host was perfect - highly recommend."
United States
Melissa T.
The price is AEDĀ 422
AEDĀ 1,017 total
includes taxes & fees
1 Dec - 2 Dec
La Casita: A Cozy Retreat Near Wake Forest University"

16. Charming house in Washington Park, W-S, NC

Charming house in Washington Park, W-S, NC
Winston-Salem
10.0 out of 10, Exceptional, (1 review)
"Good location. The beds are exceptionally comfortable. Had a small issue with the couch but he came right over to fix it"
Canada
Robert B.
The price is AEDĀ 360
AEDĀ 581 total
includes taxes & fees
12 Nov - 13 Nov
Charming house in Washington Park, W-S, NC

17. 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 AEDĀ 364
AEDĀ 868 total
includes taxes & fees
8 Nov - 9 Nov
Cozy 3BR Home Near Fairgrounds and Downtown

18. 4 Beds | King | 85ā€ TV | 5min to WSSU & Downtown

4 Beds | King | 85ā€ 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
The price is AEDĀ 393
AEDĀ 890 total
includes taxes & fees
15 Nov - 16 Nov
4 Beds | King | 85ā€ TV | 5min to WSSU & Downtown

19. Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem

Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
Winston-Salem
9.6 out of 10, Exceptional, (14 reviews)
"We loved this little cabin! Would definitely recommend!"
United States
Kathryn P.
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem

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

Downtown Charm, 3 Bdr, Near Rest and Bars
Winston-Salem
9.4 out of 10, Exceptional, (30 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 AEDĀ 558
AEDĀ 1,189 total
includes taxes & fees
8 Dec - 9 Dec
Downtown Charm, 3 Bdr, Near Rest and Bars
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.

Find vacation rentals that suit your style

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Frequently Asked Questions

Can I find vacation rentals in Winston-Salem?

Yes, there are vacation rentals in Winston-Salem close to Salem College Elberson Fine Arts Center, or you can go with a more secluded option if you'd like a relaxing place to stay. Visitors like the array of shops and lush forest in Winston-Salem. Make sure to also enjoy the college campus and top-notch restaurants during your vacation.

What are some of the best vacation rentals that Winston-Salem has to offer?

Arcade Kid Friendly Firepit Grill HotTub: This highly rated vacation home rental in Winston-Salem is located near the airport and has a fireplace, a private balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Other favorite homes for rent in Winston-Salem are Cozy 2-bedroom bungalow in lovely Winston-Salem and Quiet, newly renovated. Near everything!.

How many vacation rentals will I find in Winston-Salem?

Choose from 210 Expedia vacation rentals in Winston-Salem for a memorable vacation.

What can I see and do in Winston-Salem?

Enjoy the outdoors at Reynolda Gardens and Salem Lake, or simply take in cultural attractions like Old Salem and Reynolda House Museum of American Art. Truist Stadium and Bowman Gray Stadium are other places to visit while you're in town.

What are vacation rentals like in Winston-Salem?

Vacation rentals are privately owned properties you can book for several days or longer in Winston-Salem. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family gatherings.