Aerial View as Night Falls on the Downtown City Skyline at Winston-Salem

Winston-Salem Holiday Rentals

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Our top choices for Winston-Salem holiday rentals

Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
4.0 star property
Winston-Salem
The price is NZ$814
includes taxes & fees
7 July - 8 July
Winston Sleeps 16 - 2 Kitchens Hot Tub

Cozy Cottage: Nature-filled Winston-salem Retreat!

Cozy Cottage: Nature-filled Winston-salem Retreat!
3.0 star property
Winston-Salem
The price is NZ$942
includes taxes & fees
22 June - 23 June
Cozy Cottage: Nature-filled Winston-salem Retreat!

Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub
4.0 star property
Winston-Salem
The price is NZ$3,345
includes taxes & fees
23 June - 24 June
Arcade Kid Friendly Firepit Grill HotTub

The Ardmore Executive Suite

The Ardmore Executive Suite
4.0 star property
Winston-Salem
7.6 out of 10, Good, (5 reviews)
"Still very confused about payment process. Host asked me to send additional money on weird sources. But stay was great!"
United States
Daniel
The price is NZ$317
includes taxes & fees
24 June - 25 June
The Ardmore Executive Suite

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)
"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 NZ$501
includes taxes & fees
24 June - 25 June
King Beds Hot Tub Arcade Grill & Firepit

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 NZ$537
includes taxes & fees
29 June - 30 June
Heated Pool King Bed Jacuzzi Bath Arcade

Exec Suite King Bed Hot Tub Gym Laundry

Exec Suite King Bed Hot Tub Gym Laundry
4.5 star property
Kernersville
The price is NZ$264
includes taxes & fees
29 June - 30 June
Exec Suite King Bed Hot Tub Gym Laundry

9 Mi to Uncg & Dtwn: Suburban Family Condo

9 Mi to Uncg & Dtwn: Suburban Family Condo
3.0 star property
Greensboro
The price is NZ$582
includes taxes & fees
22 June - 23 June
9 Mi to Uncg & Dtwn: Suburban Family Condo

StudioRes by Marriott Greensboro Airport

StudioRes by Marriott Greensboro Airport
2.5 star property
Greensboro
9.6 out of 10, Exceptional, (4 reviews)
"Rooms were clean and modern. There are good stuff near by such as top golf or stores less than 5 minutes."
United States
Andres
The price is NZ$175
includes taxes & fees
23 June - 24 June
StudioRes by Marriott Greensboro Airport

KingBed Hot Tub BBQ Games Hypoallergenic

KingBed Hot Tub BBQ Games Hypoallergenic
4.0 star property
Kernersville
4.8 out of 10, (3 reviews)
"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 NZ$361
includes taxes & fees
29 June - 30 June
KingBed Hot Tub BBQ Games Hypoallergenic
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

Find out more about Winston-Salem

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winston-Salem holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winston-Salem. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winston-Salem. Seeing all the best attractions is bound to make you fall in love with Winston-Salem. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winston-Salem short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find holiday rentals in Winston-Salem?

Yes, there are holiday rentals in Winston-Salem close to Salem College Elberson Fine Arts Center, 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.

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

Quiet, newly renovated. Near everything!: This highly rated holiday home rental in Winston-Salem offers a fireplace, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Southeastern Center for Contemporary Art. Truist Stadium and Joe White Tennis Center at Hanes Park 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.