Winston-Salem Holiday Rentals

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Holiday Rentals in Winston-Salem

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 NZ$433
includes taxes & fees
10 Nov - 11 Nov
Heated Pool King Bed Jacuzzi Bath Arcade

3 mins from Downtown - PS5, King Bed & EV Charger

2.0 star property
Winston-Salem
8.6 out of 10, Excellent, (11)
"This unit would be fine for an overnight stay but my husband and I stayed for a week and did not find it adequate. For instance, it has a comfortable bed, however, except for 3 flimsy stools in the kitchen, there are no chairs nor sofa to watch tv or read. As for the bathroom, there is a large gap all along the wall and the bathtub insert and the rusty drain is exposed. Moreover, there are no hooks to hang your used towels which becomes necessary if staying for longer than a night. Lastly,...
United States
Allan S.
The price is NZ$344
includes taxes & fees
9 Nov - 10 Nov
3 mins from Downtown - PS5, King Bed & EV Charger

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 NZ$347
includes taxes & fees
16 Nov - 17 Nov
King Beds Hot Tub Arcade Grill & Firepit

Chic 2BR/2BA Near Dining & Shops

2.0 star property
Winston-Salem
9.0 out of 10, Wonderful, (2)
"This house was a nice spot to gather while we visited our son at school. We enjoyed the location and were able to walk around and visit the cute nearby shops while we waited to check in. (When we arrived, we learned that the guests before us had left a mess, so the woman who was cleaning the place wasn’t finished yet. She did a great job, though—it was in good shape when we were able to get settled in.The house did have some minor issues: one of the chairs at the dining table seemed like it was...
United States
Susan J.
The price is NZ$453
includes taxes & fees
11 Nov - 12 Nov
Chic 2BR/2BA Near Dining & Shops

Arcade Kid Friendly Firepit Grill HotTub

3.5 star property
Winston-Salem
The price is NZ$773
includes taxes & fees
10 Nov - 11 Nov
Arcade Kid Friendly Firepit Grill HotTub

Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem

Winston-Salem
9.6 out of 10, Exceptional, (5)
"It was perfect for our needs! Ty so much for a great place to stay!"
United States
Bobby
The price is NZ$455
includes taxes & fees
9 Nov - 10 Nov
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem

Cozy 3BR Home Near Fairgrounds and Downtown

2.0 star property
Winston-Salem
The price is NZ$409
includes taxes & fees
12 Nov - 13 Nov
Cozy 3BR Home Near Fairgrounds and Downtown

Updated 1BR cottage on private acre+ lot

Winston-Salem
10.0 out of 10, Exceptional, (14)
"I will love to recommend this home away from home. It’s very close to everything and a very peaceful stay. "
United States
Nina J.
The price is NZ$236
includes taxes & fees
12 Nov - 13 Nov
Updated 1BR cottage on private acre+ lot

Urban Escape 3 Bed 2.5 Bath Near Wake Forest

Winston-Salem
10.0 out of 10, Exceptional, (4)
"A very comfortable and spacious house with all the amenities you need!"
United States
Bethel S.
The price is NZ$464
includes taxes & fees
8 Dec - 9 Dec
Urban Escape 3 Bed 2.5 Bath Near Wake Forest

1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed

Winston-Salem
9.6 out of 10, Exceptional, (5)
"The cottage was super cozy; I absolutely loved it. Although our stay was short, I enjoyed it very much because of this cottage and Katy. Katy made sure we had everything we needed at all times, and she was an amazing host. I definitely would recommend this VRBO experience to anyone and everyone!"
United States
Tori B.
The price is NZ$190
includes taxes & fees
30 Nov - 1 Dec
1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed

Three bedroom 5 minutes to state university & town, 10 min to baptist hospital

Winston-Salem
8.4 out of 10, Very good, (15)
"Nice house but rough neighborhood"
United States
Doug S.
The price is NZ$374
includes taxes & fees
9 Nov - 10 Nov
Three bedroom 5 minutes to state university & town, 10 min to baptist hospital

Charming Condo Near WFU, Full Kitchen, Strong WiFi, Charming condo near WFU, full kitchen, strong Wi

Winston-Salem
10.0 out of 10, Exceptional, (2)
"Nice, quiet condo a short walk from WF campus and stadiums."
United States
Pete H.
The price is NZ$636
includes taxes & fees
11 Nov - 12 Nov
Charming Condo Near WFU, Full Kitchen, Strong WiFi, Charming condo near WFU, full kitchen, strong Wi

The Red Door Cabin

Winston-Salem
10.0 out of 10, Exceptional, (17)
"Cozy and easy place to land. If you’re looking for a spot outside of town and tucked in some woods and easy to get to, this is the spot. Super easy and comfortable."
United States
Juli M.
The price is NZ$479
includes taxes & fees
11 Nov - 12 Nov
The Red Door Cabin

Winston Sleeps 16 - 2 Kitchens Hot Tub

3.5 star property
Winston-Salem
The price is NZ$720
includes taxes & fees
17 Nov - 18 Nov
Winston Sleeps 16 - 2 Kitchens Hot Tub

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

Winston-Salem
9.6 out of 10, Exceptional, (15)
"Proximity to campus "
United States
Marcia K.
The price is NZ$424
includes taxes & fees
10 Nov - 11 Nov
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

Downtown Charm, 3 Bdr, Near Rest and Bars

Winston-Salem
9.2 out of 10, Wonderful, (17)
"Good spot with easy access to the medical appointments that we were in town for. Easy walk to a good restaurant and comfortable space. Had all that we needed for a quick stay. "
United States
Amy A.
The price is NZ$461
includes taxes & fees
8 Dec - 9 Dec
Downtown Charm, 3 Bdr, Near Rest and Bars

Hartman Casita! Quiet neighborhood.1 king Bed!

Winston-Salem
9.8 out of 10, Exceptional, (20)
"Beautiful house with everything you need with great proximity to Winston Salem. Host is friendly and very prompt with communication"
United States
Kevin D.
The price is NZ$776
includes taxes & fees
1 Dec - 2 Dec
Hartman Casita! Quiet neighborhood.1 king Bed!

The Hot Tub Hideaway

Winston-Salem
9.6 out of 10, Exceptional, (26)
"Very cozy and nice area. Off the beaten path. "
United States
Vicki O.
The price is NZ$473
includes taxes & fees
9 Nov - 10 Nov
The Hot Tub Hideaway

Spacious 3-Bedroom with 4 beds, Fully Furnished Home Near Downtown Winston-Salem

Winston-Salem
10.0 out of 10, Exceptional, (2)
"We enjoyed our short stay, house is very cute and cozy and well put together "
United States
Anonymous traveller
The price is NZ$433
includes taxes & fees
9 Nov - 10 Nov
Spacious 3-Bedroom with 4 beds, Fully Furnished Home Near Downtown Winston-Salem

The Ardmore Executive Suite

3.5 star property
Winston-Salem
6.0 out of 10, (3)
"Starts off the pictures are lies. I booked thinking I was getting a great place. They put me in the basement. Entrance was broken. Entry was nasty. The place had crumbs and hair. The huge TV didn’t work. Pillowcase didn’t fit the pillow. Bugs crawling including roaches. Child safety locks on everything. Holes in walls. Prey you don’t stay there and others are upstairs you will hear every footstep and conversation. Grill was rusted and nasty. Hot tub be prepared to pay extra as well...
United States
Anonymous traveller
The price is NZ$354
includes taxes & fees
11 Nov - 12 Nov
The Ardmore Executive Suite
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

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$300 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. 

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.

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

The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!: This highly rated holiday home rental in Winston-Salem offers a fireplace, a patio and a BBQ 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 that 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 Charming 4-bedroom house with AC and WiFi in wonderful Winston-Salem.

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

Choose from 191 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 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.