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Search Holiday Rentals in Winston-Salem

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Check prices for these dates

Tonight
18 Dec - 19 Dec
Tomorrow
19 Dec - 20 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Winston-Salem holiday rentals

House | Private kitchen | Fridge, microwave, oven, stovetop
King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit
4.0 star property
Winston-Salem
8.0 out of 10, Very good, (1)
"House was clean and amenities were good. House is in a great location. Be aware that there is another rental unit downstairs that may have other parties occuppying."
United States
Elizabeth
The price is 2.812.151 ₫
7.127.380 ₫ total
includes taxes & fees
31 Dec - 1 Jan 2026
King Beds Hot Tub Arcade Grill & Firepit
Studio | Living area | 50-inch TV with digital channels
Landing Winston-Salem near Wake Forest University

Landing Winston-Salem near Wake Forest University

Landing Winston-Salem near Wake Forest University
4.0 star property
Winston-Salem
6.4 out of 10, (5)
"I ended up not staying at the property. When I arrived, there were blowers under the carpet and in the kitchen, apparently due to a recent flood. I took one look at this Hellhole and called Landing to cancel."
United States
Eric
Landing Winston-Salem near Wake Forest University
4 bedrooms, hypo-allergenic bedding, in-room safe, blackout curtains
Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade
4.0 star property
Winston-Salem
8.0 out of 10, Very good, (1)
"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 4.170.830 ₫
8.095.519 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Heated Pool King Bed Jacuzzi Bath Arcade
Business Apartment | Private kitchen | Fridge, microwave, stovetop, dishwasher
The Ardmore Executive Suite

The Ardmore Executive Suite

The Ardmore Executive Suite
3.5 star property
Winston-Salem
6.0 out of 10, (3)
"Very clean and nice setup "
United States
Nicholas
The price is 2.978.036 ₫
5.340.006 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Ardmore Executive Suite
House | Terrace/patio
Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
3.5 star property
Winston-Salem
The price is 3.981.247 ₫
11.055.228 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Winston Sleeps 16 - 2 Kitchens Hot Tub
Free WiFi, bed sheets
InTown Suites Extended Stay Greensboro NC - Airport

InTown Suites Extended Stay Greensboro NC - Airport

InTown Suites Extended Stay Greensboro NC - Airport
2.0 star property
Greensboro
6.2 out of 10, (671)
"Front desk was handled very beautifully."
United States
Kevin
InTown Suites Extended Stay Greensboro NC - Airport
Children’s activities
Kernersville Hot Tub Pool Arcade Gym Wifi Coffee

Kernersville Hot Tub Pool Arcade Gym Wifi Coffee

Kernersville Hot Tub Pool Arcade Gym Wifi Coffee
3.0 star property
Kernersville
6.0 out of 10, (4)
"The house was very nice. Very well kept up. Enjoyed the atmosphere. Hope to stay there again. Great experience. 😃"
United States
Troy
Kernersville Hot Tub Pool Arcade Gym Wifi Coffee
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

Hampton Inn & Suites Winston-Salem Downtown

Hampton Inn & Suites Winston-Salem Downtown

10/10 Excellent
"Staff, specifically the valet driver on the night I checked. The room was clean, great location, and view. "
Angelica 1-night trip
Posted 1 day ago
Hampton Inn & Suites Winston-Salem Downtown

Frequently asked questions

Can I find holiday rentals in Winston-Salem?

Yes, there are holiday rentals in Winston-Salem close to Airbound Trampoline Park, 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.

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

Choose from 213 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.