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Search Holiday Rentals in Winston-Salem

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Check prices for these dates

Tonight
23 Dec - 24 Dec
Tomorrow
24 Dec - 25 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Winston-Salem holiday rentals

Exterior
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 3.349.558 ₫
7.734.950 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
King Beds Hot Tub Arcade Grill & Firepit
House (3 Bedrooms) | Interior
Cozy Cottage: Nature-filled Winston-salem Retreat!

Cozy Cottage: Nature-filled Winston-salem Retreat!

Cozy Cottage: Nature-filled Winston-salem Retreat!
3.0 star property
Winston-Salem
The price is 4.186.629 ₫
11.975.865 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Cottage: Nature-filled Winston-salem Retreat!
In-room dining
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 5.087.149 ₫
9.130.958 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Heated Pool King Bed Jacuzzi Bath Arcade
Fridge, microwave, oven, stovetop
Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub
3.5 star property
Winston-Salem
The price is 4.581.594 ₫
11.759.950 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Arcade Kid Friendly Firepit Grill HotTub
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
7 Jan - 8 Jan 2026
Winston Sleeps 16 - 2 Kitchens Hot Tub
Exterior
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 3.286.358 ₫
5.688.560 ₫ total
includes taxes & fees
25 Dec - 26 Dec
The Ardmore Executive Suite
Seasonal outdoor pool, pool umbrellas, pool loungers
KingBed Hot Tub BBQ Games Hypoallergenic

KingBed Hot Tub BBQ Games Hypoallergenic

KingBed Hot Tub BBQ Games Hypoallergenic
3.5 star property
Kernersville
4.8 out of 10, (3)
"We ended up not staying because after i booked they listed all the fees. You have to check in by 8 pm but is listed as 2:30am and there is a $20 per person per day fee to use the pool. And you have to give a 48 hr notice to even use the pool and i booked last minute so that would have been a waste too. To use the hot tub its $100 extra but that is the only thing listed before you book. It would not have been worth the 3.5 hr drive we were going to make. "
United States
Tiffany
The price is 3.423.030 ₫
5.842.849 ₫ total
includes taxes & fees
25 Dec - 26 Dec
KingBed Hot Tub BBQ Games Hypoallergenic
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
BBQ/picnic Area
Exec Suite King Bed Hot Tub Gym Laundry

Exec Suite King Bed Hot Tub Gym Laundry

Exec Suite King Bed Hot Tub Gym Laundry
4.0 star property
Kernersville
The price is 5.599.054 ₫
8.301.906 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Exec Suite King Bed Hot Tub Gym Laundry
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/University Area, NC

Hampton Inn & Suites Winston-Salem/University Area, NC

10/10 Excellent
"An excellent stay. Easy to find, welcoming accommodating staff, very quiet. many restaurants nearly "
Daniel 1-night trip
Posted 2 days ago
Hampton Inn & Suites Winston-Salem/University Area, NC

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 215 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.