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

Search Vacation Homes in Winston-Salem

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winston-Salem vacation homes

Business Apartment | Private kitchen | Espresso maker, coffee/tea maker, fridge, microwave

1. 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 ￥11,715
￥29,014 total
includes taxes & fees
Aug 19 - Aug 20
The Ardmore Executive Suite
Terrace/patio

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

Cozy 2-bedroom bungalow in lovely Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (32 reviews)
"Great place to stay we appreciate it being dog friendly"
United States
Melinda P.
The price is ￥18,600
￥38,134 total
includes taxes & fees
Aug 12 - Aug 13
Cozy 2-bedroom bungalow in lovely Winston-Salem
Outdoor dining

3. La Casita .

La Casita .
Winston-Salem
9.4 out of 10, Exceptional, (10 reviews)
"The location was perfect for what we needed."
United States
Giuliana
The price is ￥12,069
￥29,861 total
includes taxes & fees
Aug 20 - Aug 21
La Casita .
4 bedrooms, hypo-allergenic bedding available, in-room safe

4. 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 ￥31,435
￥74,962 total
includes taxes & fees
Aug 24 - Aug 25
Heated Pool King Bed Jacuzzi Bath Arcade
Coffee/tea maker, fridge, microwave, oven

5. 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 ￥15,737
￥41,324 total
includes taxes & fees
Aug 12 - Aug 13
Chic 2BR/2BA Near Dining & Shops
Exterior

6. 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 ￥17,748
￥38,239 total
includes taxes & fees
Aug 12 - Aug 13
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
House | Terrace/patio

7. Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
4.0 star property
Winston-Salem
The price is ￥22,541
￥64,912 total
includes taxes & fees
Aug 13 - Aug 14
Winston Sleeps 16 - 2 Kitchens Hot Tub
Coffee/tea maker, fridge, microwave, oven

8. 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 ￥16,880
￥42,251 total
includes taxes & fees
Aug 12 - Aug 13
La Casita: A Cozy Retreat Near Wake Forest University"
Dining

9. 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 ￥20,824
￥49,847 total
includes taxes & fees
Sep 7 - Sep 8
Downtown Charm, 3 Bdr, Near Rest and Bars
Iron/ironing board, travel crib, WiFi, bed sheets

10. 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 ￥14,987
￥39,831 total
includes taxes & fees
Aug 20 - Aug 21
Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds
Terrace/patio

11. 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 ￥23,853
￥42,999 total
includes taxes & fees
Aug 13 - Aug 14
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
Private kitchen

12. 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 ￥14,908
￥33,603 total
includes taxes & fees
Aug 24 - Aug 25
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
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
The price is ￥15,618
￥41,219 total
includes taxes & fees
Aug 31 - Sep 1
Cozy 3BR Home Near Fairgrounds and Downtown
House | Private kitchen | Espresso maker, coffee/tea maker, fridge, microwave

14. 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 ￥30,361
￥57,973 total
includes taxes & fees
Aug 16 - Aug 17
King Beds Hot Tub Arcade Grill & Firepit
Coffee/tea maker, fridge, microwave, oven

15. 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, (6 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.
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
Private kitchen

16. La Casita #3

La Casita #3
Winston-Salem
The price is ￥11,359
￥1,407,611 total
includes taxes & fees
Aug 17 - Aug 18
La Casita #3
Coffee/tea maker, fridge, microwave, oven

17. Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown

Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Winston-Salem
9.2 out of 10, Wonderful, (17 reviews)
"Perfect place for a couple guys for one night stop on our way south for a golf trip. Quick/cheap uber ride to restaurants/town and very clean house!"
United States
Patrick R.
The price is ￥21,298
￥50,629 total
includes taxes & fees
Aug 12 - Aug 13
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Coffee/tea maker, fridge, microwave, oven

18. 3 King Beds | XL TVs | Near Hospital, College & DT

3 King Beds | XL TVs | Near Hospital, College & DT
Winston-Salem
8.4 out of 10, Very Good, (15 reviews)
"Great stay with family. "
United States
Tyler J.
The price is ￥15,618
￥38,582 total
includes taxes & fees
Sep 7 - Sep 8
3 King Beds | XL TVs | Near Hospital, College & DT
Terrace/patio

19. 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.
The price is ￥21,156
￥47,617 total
includes taxes & fees
Aug 23 - Aug 24
Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!
House | 5 bedrooms, hypo-allergenic bedding available, laptop workspace

20. Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub
4.0 star property
Winston-Salem
The price is ￥22,656
￥65,041 total
includes taxes & fees
Aug 14 - Aug 15
Arcade Kid Friendly Firepit Grill HotTub
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winston-Salem Hotel Reviews

Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

8/10 Good
"The beds were comfortable and good water pressure in shower. A/C could have worked better but overall a great stay"
Elijah 1-night trip
Posted 1 hour ago
Hawthorne Inn and Conference Center

Find out more about Winston-Salem

Winston-Salem Vacation Homes information

Number of reviews
Accommodation
 Vacation Homes
Lowest Price
Highest Price