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Winston-Salem Vacation Rentals

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Check prices for these dates

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

Our top choices for Winston-Salem vacation rentals

Exterior
King Beds Hot Tub Arcade Grill & Firepit

Residence in Winston-Salem

King Beds Hot Tub Arcade Grill & Firepit
4.0 star property
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 ￥19,559
￥45,637 total
includes taxes & fees
Jan 8 - Jan 9, 2026
King Beds Hot Tub Arcade Grill & Firepit
House (3 Bedrooms) | Interior
Cozy Cottage: Nature-filled Winston-salem Retreat!

Cottage in Winston-Salem

Cozy Cottage: Nature-filled Winston-salem Retreat!
3.0 star property
The price is ￥24,947
￥71,361 total
includes taxes & fees
Dec 24 - Dec 25
Cozy Cottage: Nature-filled Winston-salem Retreat!
In-room dining
Heated Pool King Bed Jacuzzi Bath Arcade

Residence in Winston-Salem

Heated Pool King Bed Jacuzzi Bath Arcade
4.0 star property
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 ￥29,372
￥53,345 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Heated Pool King Bed Jacuzzi Bath Arcade
Fridge, microwave, oven, stovetop
Arcade Kid Friendly Firepit Grill HotTub

Residence in Winston-Salem

Arcade Kid Friendly Firepit Grill HotTub
3.5 star property
The price is ￥27,301
￥70,075 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Arcade Kid Friendly Firepit Grill HotTub
House | Terrace/patio
Winston Sleeps 16 - 2 Kitchens Hot Tub

Residence in Winston-Salem

Winston Sleeps 16 - 2 Kitchens Hot Tub
3.5 star property
The price is ￥23,723
￥65,875 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Winston Sleeps 16 - 2 Kitchens Hot Tub
Exterior
The Ardmore Executive Suite

Residence in Winston-Salem

The Ardmore Executive Suite
3.5 star property
6.0 out of 10, (3)
"Very clean and nice setup "
United States
Nicholas
The price is ￥19,581
￥33,893 total
includes taxes & fees
Dec 26 - Dec 27
The Ardmore Executive Suite
Seasonal outdoor pool, pool umbrellas, sun loungers
KingBed Hot Tub BBQ Games Hypoallergenic

Residence in Kernersville

KingBed Hot Tub BBQ Games Hypoallergenic
3.5 star property
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 ￥19,887
￥34,240 total
includes taxes & fees
Dec 26 - Dec 27
KingBed Hot Tub BBQ Games Hypoallergenic
Children's activities
Kernersville Hot Tub Pool Arcade Gym Wifi Coffee

Vacation Home in Kernersville

Kernersville Hot Tub Pool Arcade Gym Wifi Coffee
3.0 star property
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

Residence in Kernersville

Exec Suite King Bed Hot Tub Gym Laundry
4.0 star property
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

Holiday Inn Express Winston-Salem Medical Center Area by IHG

Holiday Inn Express Winston-Salem Medical Center Area by IHG

10/10 Excellent
"Quiet, clean and staff was great."
Victoria 1-night trip
Posted 2 days ago
Holiday Inn Express Winston-Salem Medical Center Area by IHG

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 vacation rentals in Winston-Salem?

Yes, there are vacation rentals in Winston-Salem close to Airbound Trampoline Park, or you can go with a more secluded option if you'd like a relaxing place to stay. Visitors like the array of shops and lush forest in Winston-Salem. Make sure to also enjoy the college campus and top-notch restaurants during your vacation.

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

The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!: This Winston-Salem vacation home rental offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Another good choice for your trip to Winston-Salem is La Casita: A Cozy Retreat Near Wake Forest University".

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

Choose from 215 Expedia vacation rentals in Winston-Salem for a memorable vacation.

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 vacation rentals like in Winston-Salem?

Vacation rentals are privately owned properties you can book for several days or longer in Winston-Salem. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family gatherings.