Winston-Salem Holiday Rentals

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Holiday Rentals in Winston-Salem

The Red Door Cabin
10.0 out of 10, Exceptional, (9)
"The property was described properly Communication with host was great. Couple of suggestions: 1: Need more eating utensils 2: shower area is dark not sure how to improve rhat 3: more sitting in living area mayne a very small sectional or sofa with a chaise. Had a wonderful weekend"
The price is NZ$459
includes taxes & fees
6 Dec - 7 Dec
The Red Door Cabin
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
10.0 out of 10, Exceptional, (20)
"The place is cozy with clever designs, such as the coffee table that converts to a dining table. I think Kumi has thought of everything that would make a stay comfortable. Blue H2O is very welcoming as soon as you walk in. The bed was comfortable, on the softer side, with very puffy pillows. The hot tub was relaxing. We didn’t spend much time in the backyard as it was rainy and cloudy, but our dogs enjoyed it. "
The price is NZ$394
includes taxes & fees
6 Dec - 7 Dec
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
Cozy Townhome in a Great Location
10.0 out of 10, Exceptional, (18)
"Property was perfect. Very clean and well stock. Great location for where we needed to be. Excellent communication with host. 5 stars all the way"
Cozy Townhome in a Great Location
3 Bedroom -1 mile from Mall and Hospital. - Long Term Allowed
9.0 out of 10, Wonderful, (30)
"House was clean, beds were comfortable, and convenient to hospital only 10 mins drive."
3 Bedroom -1 mile from Mall and Hospital. - Long Term Allowed
Remodeled historic home! Steps away from dining & shops - Easy walk to Old Salem
10.0 out of 10, Exceptional, (46)
"We loved our stay at this charming little house! It was so beautifully renovated, clean and well equipped and the owners were great. It felt so cozy and homey. We will definitely be back!"
Remodeled historic home! Steps away from dining & shops - Easy walk to Old Salem
High ceiling house close to downtown
6.0 out of 10, (4)
"A comfortable little home with comfortable beds for those who may be in town for business. Folks in the neighborhood approached me on more than one occassion for a cigarette. Would not stay in this area alone."
The price is NZ$459
includes taxes & fees
23 Nov - 24 Nov
High ceiling house close to downtown
Charming Winston-Salem Studio on Miller Park!
9.6 out of 10, Exceptional, (13)
"We stayed for 2 nights because of a medical trip. This was an excellent home base for my husband and I. The studio was immaculate and probably the cleanest property I have ever stayed in. Everything was comfortable and we were equipped with what we needed and more. I have more trips to come in my future and I would love to stay here again."
The price is NZ$311
includes taxes & fees
28 Nov - 29 Nov
Charming Winston-Salem Studio on Miller Park!
Hartman Casita! Quiet neighborhood.1 king Bed!
10.0 out of 10, Exceptional, (15)
"House is very nice and roomy and in a very nice neighborhood. With one minor exception everything was great. "
The price is NZ$786
includes taxes & fees
26 Nov - 27 Nov
Hartman Casita! Quiet neighborhood.1 king Bed!
Luxury tent on lowery mill creek
5.0 out of 10, (2)
"this place doesnt exist, and i have yet to get paid back. i have been staying in a car with my kids because i have no place to stay and my money is tied up in this BS"
Luxury tent on lowery mill creek
Historic West End Hideaway, walk to downtown WS
10.0 out of 10, Exceptional, (13)
"The owners take much pride in their property and the overall experience. The house is clean, well labeled and perfect for a family gathering. We thoroughly enjoyed our stay at the Hideaway."
Historic West End Hideaway, walk to downtown WS
The Cook's Wall Cabin
9.8 out of 10, Exceptional, (92)
"The hosts were friendly, helpful, and thoughtful in their preparation of the cabin. Also, a great price for nice accommodations, convenient to Hanging Rock State Park. I’d also recommend making a stop at John Brown’s Country Store."
The price is NZ$203
includes taxes & fees
24 Nov - 25 Nov
The Cook's Wall Cabin
The Lakeview House - access to pier/dock, fire pit and lake access
9.8 out of 10, Exceptional, (100)
"The house and view were amazing. Owner is very helpful and kind. Property was very clean and spacious. We couldnt have been happier with our stay!"
The Lakeview House - access to pier/dock, fire pit and lake access
Great High Point Location adj to JH Adams Inn- Newly Renovated
10.0 out of 10, Exceptional, (57)
"We chose this as a place to get ready for the wedding and stay afterward as it was apart from the guests who were at a hotel. The house had a lot of space downstairs to hangout and get make up done. The upstairs had three bedrooms with a master with an amazing bathroom. The beds were super comfortable and felt clean. My only complaint is as a tall person there is a low chandelier in the master that we tend to bump our head on other than that just like the photos. Great location with walk ability...
Great High Point Location adj to JH Adams Inn- Newly Renovated
Quaint 2 bed 1 bath cottage style home
9.4 out of 10, Exceptional, (28)
"In town for a wedding in Kernersville and the house was perfect! Very cute, comfortable and in a quiet neighborhood. Highly recommend!"
The price is NZ$344
includes taxes & fees
24 Nov - 25 Nov
Quaint 2 bed 1 bath cottage style home
Shalimar Estates @ Emerywood and Downtown/HPU
9.4 out of 10, Exceptional, (6)
"Great stay! "
The price is NZ$1,808
includes taxes & fees
24 Nov - 25 Nov
Shalimar Estates @ Emerywood and Downtown/HPU
Updated High Point Retreat w/ Pool & Backyard
10.0 out of 10, Exceptional, (12)
"Great place to stay!! We enjoyed all the amenities provided. Good open are to visit and relax. We plan to return! "
Updated High Point Retreat w/ Pool & Backyard
Secluded close to everything!
8.0 out of 10, Very good, (3)
"This house met all of our needs! It was clean, spacious, had a great back deck to hang out on. We would definitely stay again. Thank you!"
The price is NZ$635
includes taxes & fees
24 Nov - 25 Nov
Secluded close to everything!
⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close
9.8 out of 10, Exceptional, (38)
"We enjoyed the house. It was perfect for what we needed. "
⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close
Charming Remodeled 4 Bedroom Home in Downtown High Point
10.0 out of 10, Exceptional, (61)
"This is my second time booking Sherri’s beautiful home, and once again, it was perfect! The house is spacious, well-maintained, and ideal for hosting our family gathering. Every detail is thoughtfully taken care of, making the stay seamless and enjoyable. Sherri is an incredible host, responsive and accommodating. We’ll definitely be back. Highly recommend!"
Charming Remodeled 4 Bedroom Home in Downtown High Point
Beautiful apt Downtown perfect for long term stays
8.8 out of 10, Excellent, (22)
"Great location and price. Scott was awesome and quick to communicate. "
The price is NZ$247
includes taxes & fees
27 Nov - 28 Nov
Beautiful apt Downtown perfect for long term stays
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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Other types of properties in Winston-Salem you may be interested in

Best Western Plus University Inn
3.5 star property
7.6 out of 10, Good, (1001)
"Overall a good stay. Only issues were in the bathroom. Shower faucets were mixed up (hot faucet put out cold water) and bathroom fan did not work."
The price is NZ$129
includes taxes & fees
3 Dec - 4 Dec
Best Western Plus University Inn
HomeTowne Studios by Red Roof Winston-Salem - University Pkwy
2.0 star property
5.6 out of 10, (1042)
"I enjoyed my stay "
The price is NZ$100
includes taxes & fees
3 Dec - 4 Dec
HomeTowne Studios by Red Roof Winston-Salem - University Pkwy
La Quinta Inn & Suites by Wyndham Winston-Salem
2.5 star property
7.0 out of 10, Good, (1003)
"An older hotel but clean and spacious room. Staff was nice. Free breakfast was okay, nothing special."
The price is NZ$134
includes taxes & fees
3 Dec - 4 Dec
La Quinta Inn & Suites by Wyndham Winston-Salem
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.
Beautiful view of the beach with palm trees

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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 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?

3 Bedroom -1 mile from Mall and Hospital. - Long Term Allowed: This highly rated holiday home rental in Winston-Salem is on a lake, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Winston-Salem are High ceiling house close to downtown and Hartman Casita! Quiet neighborhood.1 king Bed!.

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

Choose from 164 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 Old Town Park, 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.