A cityscape with various buildings, including a prominent skyscraper and several mid-rise structures.

Winston-Salem Vacation Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winston-Salem vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. Updated 1BR cottage on private acre+ lot

Updated 1BR cottage on private acre+ lot
Winston-Salem
10.0 out of 10, Exceptional, (26 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.
Updated 1BR cottage on private acre+ lot
Property grounds

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, (28 reviews)
"Great location "
United States
Heather C.
The price is AED 331
AED 552 total
includes taxes & fees
9 Aug - 10 Aug
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
Business Apartment | Private kitchen | Espresso maker, coffee/tea maker, fridge, microwave

3. 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 AED 286
AED 690 total
includes taxes & fees
9 Aug - 10 Aug
The Ardmore Executive Suite
Terrace/patio

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

Cozy 2-bedroom bungalow in lovely Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (31 reviews)
"Great place to stay we appreciate it being dog friendly"
United States
Melinda P.
The price is AED 433
AED 884 total
includes taxes & fees
12 Aug - 13 Aug
Cozy 2-bedroom bungalow in lovely Winston-Salem
Outdoor dining

5. La Casita .

La Casita .
Winston-Salem
9.8 out of 10, Exceptional, (8 reviews)
"The location was perfect for what we needed."
United States
Giuliana
The price is AED 281
AED 691 total
includes taxes & fees
9 Aug - 10 Aug
La Casita .
4 bedrooms, hypo-allergenic bedding available, in-room safe

6. 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 AED 345
AED 1,308 total
includes taxes & fees
9 Aug - 10 Aug
Heated Pool King Bed Jacuzzi Bath Arcade
Exterior

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, (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 AED 242
AED 668 total
includes taxes & fees
11 Aug - 12 Aug
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
Coffee/tea maker, fridge, microwave, oven

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

Chic 2BR/2BA Near Dining & Shops
Winston-Salem
9.4 out of 10, Exceptional, (12 reviews)
"10 out of 10 I truly recommend 😊"
United States
Charlithia
The price is AED 370
AED 1,008 total
includes taxes & fees
10 Aug - 11 Aug
Chic 2BR/2BA Near Dining & Shops
Exterior

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
9.6 out of 10, Exceptional, (20 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 AED 413
AED 886 total
includes taxes & fees
10 Aug - 11 Aug
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
1 bedroom

10. The Hot Tub Hideaway

The Hot Tub Hideaway
Winston-Salem
9.6 out of 10, Exceptional, (35 reviews)
"It was a good stay"
United States
Kim R.
The price is AED 526
AED 905 total
includes taxes & fees
8 Aug - 9 Aug
The Hot Tub Hideaway
House | Terrace/patio

11. Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
4.0 star property
Winston-Salem
The price is AED 597
AED 1,593 total
includes taxes & fees
10 Aug - 11 Aug
Winston Sleeps 16 - 2 Kitchens Hot Tub
Coffee/tea maker, fridge, microwave, oven

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, (58 reviews)
"Perfect for our family of 3 visiting WFU"
United States
Peter F.
The price is AED 383
AED 956 total
includes taxes & fees
6 Sep - 7 Sep
La Casita: A Cozy Retreat Near Wake Forest University"
Dining

13. 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 AED 485
AED 1,161 total
includes taxes & fees
7 Sep - 8 Sep
Downtown Charm, 3 Bdr, Near Rest and Bars
Iron/ironing board, travel crib, WiFi, bed sheets

14. 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 AED 349
AED 915 total
includes taxes & fees
9 Aug - 10 Aug
Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds
Terrace/patio

15. 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, (55 reviews)
"We had a very relaxing stay here. The hot tub was lovely and the property was very close to a lot of shopping/restaurants. "
United States
Taylor E.
The price is AED 555
AED 997 total
includes taxes & fees
13 Aug - 14 Aug
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
Private kitchen

16. 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, (1 review)
"Quiet area fenced in yard for our dogs it was a awesome place"
United States
Tammy C.
The price is AED 350
AED 782 total
includes taxes & fees
10 Aug - 11 Aug
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
Coffee/tea maker, fridge, microwave, oven

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 AED 364
AED 960 total
includes taxes & fees
10 Aug - 11 Aug
Cozy 3BR Home Near Fairgrounds and Downtown
House | Private kitchen | Espresso maker, coffee/tea maker, fridge, microwave

18. King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit
4.5 star property
Winston-Salem
9.4 out of 10, Exceptional, (3 reviews)
"Loved this little house and all the attention to detail! Would definitely return."
United States
Brittney N
The price is AED 2,263
AED 3,108 total
includes taxes & fees
15 Aug - 16 Aug
King Beds Hot Tub Arcade Grill & Firepit
Coffee/tea maker, fridge, microwave, oven

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, (5 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 AED 514
AED 1,316 total
includes taxes & fees
9 Aug - 10 Aug
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
Private kitchen

20. La Casita #3

La Casita #3
Winston-Salem
The price is AED 264
AED 32,942 total
includes taxes & fees
16 Aug - 17 Aug
La Casita #3
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

Spark by Hilton Winston-Salem University

Spark by Hilton Winston-Salem University

10/10 Excellent
"Excellent hotel"
Stanford A 3-night trip
Posted 8 hours ago
Spark by Hilton Winston-Salem University

Frequently asked questions

Can I find vacation rentals in Winston-Salem?

Yes, there are vacation rentals in Winston-Salem close to Airbound Trampoline Park, 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?

Quiet, newly renovated. Near everything!: This highly rated vacation home rental in Winston-Salem offers a fireplace, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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

Choose from 209 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 Southeastern Center for Contemporary 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.