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Winston-Salem Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Winston-Salem holiday 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, (29 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 HK$389
HK$1,034 total
includes taxes & fees
14 Sept - 15 Sept
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, (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 HK$706
HK$1,178 total
includes taxes & fees
13 Sept - 14 Sept
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
Exterior

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)
"Nice studio close to Miller Park. Host very easy to communicate with. My husband and I enjoyed the stay. Close to restaurants and stores as well. Would happily stay again."
United States
Catherine D.
The price is HK$517
HK$1,426 total
includes taxes & fees
9 Sept - 10 Sept
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
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, (37 reviews)
"Great place to stay we appreciate it being dog friendly"
United States
Melinda P.
The price is HK$924
HK$1,877 total
includes taxes & fees
14 Sept - 15 Sept
Cozy 2-bedroom bungalow in lovely Winston-Salem
Private kitchen

5. 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 HK$1,029
HK$2,338 total
includes taxes & fees
13 Sept - 14 Sept
King Beds Hot Tub Arcade Grill & Firepit
Private kitchen

6. 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 HK$579
HK$1,438 total
includes taxes & fees
10 Sept - 11 Sept
The Ardmore Executive Suite
Coffee/tea maker, fridge, microwave, oven

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

Chic 2BR/2BA Near Dining & Shops
Winston-Salem
9.6 out of 10, Exceptional, (14 reviews)
"Very clean and nice"
United States
Juancarlos
Chic 2BR/2BA Near Dining & Shops
Outdoor dining

8. 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 HK$600
HK$1,475 total
includes taxes & fees
9 Sept - 10 Sept
La Casita .
Private kitchen

9. 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 HK$847
HK$1,781 total
includes taxes & fees
7 Oct - 8 Oct
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
Coffee/tea maker, fridge, microwave, oven

10. Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
9.6 out of 10, Exceptional, (32 reviews)
"In town for work. Was a Great stay. Staying there again this week"
United States
Natalie K.
The price is HK$909
HK$2,064 total
includes taxes & fees
9 Sept - 10 Sept
Quiet, newly renovated. Near everything!
Dining

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

Downtown Charm, 3 Bdr, Near Rest and Bars
Winston-Salem
9.4 out of 10, Exceptional, (26 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 HK$940
HK$2,326 total
includes taxes & fees
14 Sept - 15 Sept
Downtown Charm, 3 Bdr, Near Rest and Bars
Microwave, oven, stovetop, dishwasher

12. 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.
Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!
Coffee/tea maker, fridge, microwave, oven

13. 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
Cozy 3BR Home Near Fairgrounds and Downtown
Coffee/tea maker, fridge, microwave, oven

14. 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 HK$902
HK$2,250 total
includes taxes & fees
15 Sept - 16 Sept
Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore
Exterior

15. 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 HK$980
HK$1,949 total
includes taxes & fees
9 Sept - 10 Sept
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Terrace/patio

16. Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
4.0 star property
Winston-Salem
The price is HK$1,265
HK$3,389 total
includes taxes & fees
22 Sept - 23 Sept
Winston Sleeps 16 - 2 Kitchens Hot Tub
4 bedrooms, hypo-allergenic bedding, in-room safe, blackout curtains

17. 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 HK$968
HK$3,053 total
includes taxes & fees
9 Sept - 10 Sept
Heated Pool King Bed Jacuzzi Bath Arcade
Exterior

18. 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 HK$1,122
HK$1,932 total
includes taxes & fees
9 Sept - 10 Sept
The Red Door Cabin
Iron/ironing board, travel cot, WiFi, bed sheets

19. 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.
Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds
Interior

20. Urban Escape 3 Bed 2.5 Bath Near Wake Forest

Urban Escape 3 Bed 2.5 Bath Near Wake Forest
Winston-Salem
9.2 out of 10, Wonderful, (16 reviews)
"Great stay! House was very clean with privacy. Would definitely return and stay again! "
United States
Rhonda H.
The price is HK$776
HK$2,118 total
includes taxes & fees
9 Sept - 10 Sept
Urban Escape 3 Bed 2.5 Bath Near Wake Forest
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

La Quinta Inn & Suites by Wyndham Winston-Salem

La Quinta Inn & Suites by Wyndham Winston-Salem

10/10 Excellent
"I loved the convenience of the location and it is a beautiful hotel"
Amy Marie 1-night trip
Posted 6 hours ago
La Quinta Inn & Suites by Wyndham Winston-Salem

Find out more about Winston-Salem

Search for holiday rentals in Winston-Salem on Expedia! You can easily find your home rentals, villas, holiday apartments in Winston-Salem using one of the methods below:

  • View our selection of featured holiday rentals in Winston-Salem
  • Use the map to find apartments and other holiday homes in the Winston-Salem neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winston-Salem while they last

Look no further and take a look at our great range of rental properties in Winston-Salem!

Frequently asked questions

Can I find holiday rentals in Winston-Salem?

Yes, there are holiday rentals in Winston-Salem close to Salem College Elberson Fine Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and lush forest in Winston-Salem. Make sure to also enjoy the university campus and top-notch restaurants during your holiday.

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

Cozy 2-bedroom bungalow in lovely Winston-Salem: This highly rated holiday home rental in Winston-Salem is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop and a microwave. Other favourite homes for rent in Winston-Salem are The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood! and La Casita: A Cozy Retreat Near Wake Forest University".

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

Choose from 209 Expedia holiday rentals in Winston-Salem for a memorable holiday.

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 holiday rentals like in Winston-Salem?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winston-Salem. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a family getaway.