Winston-Salem Holiday Rentals

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Holiday Rentals in Winston-Salem

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

10.0 out of 10, Exceptional, (42)
"Lovely space... super clean and cozy, close to everything in Winston-Salem but secluded enough. We will be definitely staying here again when we come back next year."
The price is AU$418
includes taxes & fees
19 Aug - 20 Aug
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

Quiet, newly renovated. Near everything!

9.8 out of 10, Exceptional, (10)
"My son was graduating from NC state but lives in Winston Salem. This was the perfect spot for 5 adults and served as a great base camp. There were many small touches included and communication was immediate. We would definitely stay here again! "
The price is AU$426
includes taxes & fees
24 Aug - 25 Aug
Quiet, newly renovated. Near everything!

The Hot Tub Hideaway

9.6 out of 10, Exceptional, (20)
"Stay is awesome!"
The price is AU$414
includes taxes & fees
19 Aug - 20 Aug
The Hot Tub Hideaway

The Ardmore Executive Suite

3.5 star property
6.0 out of 10, (3)
"Very clean and nice setup "
The Ardmore Executive Suite

Charming & Modern Home / Prime Location / Sleeps 8

9.2 out of 10, Wonderful, (7)
"Great stay and the property was pictured exactly how it was. Perfect for our family as we visited our oldest who is living in Winston-Salem."
Charming & Modern Home / Prime Location / Sleeps 8

La Casita: A Cozy Retreat Near Wake Forest University"

9.6 out of 10, Exceptional, (49)
"Great location WFU, Reynolda Rd. House very clean with well equipped kitchen. King size beds. Outdoor patio table and chairs "
The price is AU$425
includes taxes & fees
15 Sept - 16 Sept
La Casita: A Cozy Retreat Near Wake Forest University"

High ceiling house close to downtown

7.8 out of 10, Good, (8)
"Our stay was excellent! The host was very courteous and helped out a lot. The house was very clean and the beds very comfortable. My family and I really enjoyed our trip and we would recommend this property to those who want a comfortable stay at a great price."
The price is AU$298
includes taxes & fees
19 Aug - 20 Aug
High ceiling house close to downtown

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

9.6 out of 10, Exceptional, (15)
"Wonderful stay! "
The price is AU$371
includes taxes & fees
19 Aug - 20 Aug
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

King Beds Hot Tub Arcade Grill & Firepit

4.0 star property
King Beds Hot Tub Arcade Grill & Firepit

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

2.0 star property
8.4 out of 10, Very good, (8)
"Cute in-law apt. Close walk to UNCSA! Perfect for our stay. Manuel was an excellent host. Super responsive with any inquiries. "
The price is AU$301
includes taxes & fees
23 Aug - 24 Aug
3 mins from Downtown - PS5, King Bed & EV Charger

Arcade Kid Friendly Firepit Grill HotTub

3.5 star property
Arcade Kid Friendly Firepit Grill HotTub

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

9.6 out of 10, Exceptional, (5)
"The property owners were very communicative and helpful. The property itself was beautiful and cozy—a perfect place for a weekend getaway. "
1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed

Charming Cape-Cod Retreat in South Winston Salem

8.0 out of 10, Very good, (3)
"It is a new listing so I think some things need to be worked out. Pros: check in process was easy, host was very responsive to questions, house has pretty much all the basic things you need and tidy . Seems like a safe neighborhood . Cons: there is a mattress on the floor in one of the bedrooms, but otherwise the other bedrooms have actual beds. There was no ironing board or steamer. (we did contact the host to ask if there was one, and it seemed as though she was willing to bring one by , but...
Charming Cape-Cod Retreat in South Winston Salem

Country's Club Southern Comfort Retreat

10.0 out of 10, Exceptional, (1)
"Had no issues, other than locking myself out of the rental. Totally my fault and owner was quick to come over and let me in. Clean, quiet, close to lots. Great star. Thanks!"
Country's Club Southern Comfort Retreat

Cozy Winston-Salem Vacation Cabin

2.0 star property
8.0 out of 10, Very good, (2)
"Host was prompt with responses and willing to assist. Sleeping for 10 or 12 if required but semi-comfortable seating for maybe 4 people unless you count dining room seating. Water pressure very low. Outdoor area and deck had nice view but old and could use some TLC with a covered are for rain days. We left a day early and went to a hotel."
Cozy Winston-Salem Vacation Cabin

InTown Suites Extended Stay Greensboro NC - Airport

2.0 star property
6.2 out of 10, (662)
"Friendly staff/mildew odor in room"
InTown Suites Extended Stay Greensboro NC - Airport

Private pier, dock, fire pit and access to boat access on High Rock lake

9.8 out of 10, Exceptional, (58)
"We enjoyed the stay . A great location and house to relax and enjoy the lake. The owner and the host was very friendly and very courteous. Hope to stay there again sometime."
Private pier, dock, fire pit and access to boat access on High Rock lake

Charming 2-bedroom Cottage with AC and WiFi in Pilot Mountain

8.6 out of 10, Excellent, (15)
"We had a great stay for a quick trip to see family! "
The price is AU$325
includes taxes & fees
19 Aug - 20 Aug
Charming 2-bedroom Cottage with AC and WiFi in Pilot Mountain

The Lakeview House - access to pier/dock, fire pit and lake access

9.8 out of 10, Exceptional, (110)
"nice place to vacation and relax"
The Lakeview House - access to pier/dock, fire pit and lake access

Lakefront 2 BR Cottage sleeps 6 with private dock, kayaks, and heated patio

10.0 out of 10, Exceptional, (5)
Lakefront 2 BR Cottage sleeps 6 with private dock, kayaks, and heated patio
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

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?

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. Another good choice for your trip to Winston-Salem is Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!.

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

Choose from 193 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.