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Winston - Salem Holiday Rentals

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Our top choices for Winston - Salem holiday 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 NZ$216
includes taxes & fees
11 Nov - 12 Nov
Updated 1BR cottage on private acre+ lot

2. 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 traveller
The price is NZ$307
includes taxes & fees
10 Nov - 11 Nov
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!

3. 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 NZ$349
includes taxes & fees
8 Nov - 9 Nov
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.

4. 2 Full Bed|Smk|Kernersville NC

2 Full Bed|Smk|Kernersville NC
Kernersville NC
10.0 out of 10, Exceptional, (73 reviews)
"The atmosphere was peaceful with friendly staff."
United States
Anonymous traveller
The price is NZ$96
includes taxes & fees
12 Nov - 13 Nov
2 Full Bed|Smk|Kernersville NC

5. La Casita .

La Casita .
Winston-Salem
9.6 out of 10, Exceptional, (18 reviews)
"Great little place, good location, had everything we needed. We would definitely stay here again!"
United States
Kristopher J.
La Casita .

6. 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 NZ$443
includes taxes & fees
15 Nov - 16 Nov
Chic 2BR/2BA Near Dining & Shops

7. 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 NZ$490
includes taxes & fees
9 Nov - 10 Nov
Downtown Charm, 3 Bdr, Near Rest and Bars

8. 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 NZ$355
includes taxes & fees
16 Nov - 17 Nov
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA

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
The price is NZ$448
includes taxes & fees
18 Nov - 19 Nov
Cozy 3BR Home Near Fairgrounds and Downtown

10. 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)
"Wonderful stay! "
United States
Hannah J.
The price is NZ$481
includes taxes & fees
17 Nov - 18 Nov
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

11. 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 NZ$416
includes taxes & fees
8 Nov - 9 Nov
Cozy 2-bedroom bungalow in lovely Winston-Salem

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
The price is NZ$605
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 NZ$450
includes taxes & fees
8 Nov - 9 Nov
The Red Door Cabin

14. 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 NZ$495
includes taxes & fees
8 Nov - 9 Nov
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

15. 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 NZ$444
includes taxes & fees
8 Nov - 9 Nov
Quiet, newly renovated. Near everything!

16. 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 NZ$450
includes taxes & fees
8 Nov - 9 Nov
The Hot Tub Hideaway

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
The price is NZ$488
includes taxes & fees
12 Nov - 13 Nov
Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore

18. 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 NZ$282
includes taxes & fees
9 Nov - 10 Nov
Charming house in Washington Park, W-S, NC

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, (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.
The price is NZ$676
includes taxes & fees
8 Nov - 9 Nov
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University

20. Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem

Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem
Winston Salem
10.0 out of 10, Exceptional, (2 reviews)
"Great stay wonderful experience"
United States
dillon b.
The price is NZ$368
includes taxes & fees
20 Nov - 21 Nov
Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem
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 holiday rentals that suit your style

Find out more about Winston - Salem

Everything you need to know about Winston - Salem holiday rentals

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

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winston - Salem holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winston - Salem holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winston - Salem holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winston - Salem holiday rentals we have selected for you start as low as NZ$96 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winston - Salem rentals

At Expedia, we put the best Winston - Salem holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winston - Salem rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winston - Salem holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winston - Salem. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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