Winston-Salem Holiday Rentals

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Holiday Rentals in Winston-Salem

3 Bedroom -1 mile from Mall and Hospital. - Long Term Allowed

9.2 out of 10, Wonderful, (32)
"Really enjoyed the stay! William, the host, was super responsive! "
3 Bedroom -1 mile from Mall and Hospital. - Long Term Allowed

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$336
includes taxes & fees
29 Dec - 30 Dec
High ceiling house close to downtown

The Red Door Cabin

10.0 out of 10, Exceptional, (10)
"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$478
includes taxes & fees
29 Dec - 30 Dec
The Red Door Cabin

Cozy Townhome in a Great Location

10.0 out of 10, Exceptional, (19)
"We were in town for a soccer tournament and this place put us 20 minutes from any set of fields we needed for the weekend. Space was clean with the exception of a few carpet stains, which is life. This gave us a lot more space for the price of a weekend’s hotel. Will definitely consider this property again if we have another tournament in WS."
Cozy Townhome in a Great Location

Remodeled historic home! Steps away from dining & shops - Easy walk to Old Salem

10.0 out of 10, Exceptional, (48)
"Very nice property and convenient to UNCSA. The restaurant is literally in the backyard but they don’t stay open that late so we didn’t have issues."
Remodeled historic home! Steps away from dining & shops - Easy walk to Old Salem

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

10.0 out of 10, Exceptional, (23)
"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$404
includes taxes & fees
6 Jan - 7 Jan 2025
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

La Casita: A Cozy Retreat Near Wake Forest University"

9.6 out of 10, Exceptional, (46)
"Overall we had no issues, we didn’t realize it was an attached residence but that may be my error. It was a bit hard to find late at night. We also didn’t expect there to be as much emergency vehicle/traffic noise. The location is next to a busy road and the fire dept is a short distance away. We would stay again it’s a good location in terms of distance to where we needed to be. "
The price is NZ$472
includes taxes & fees
2 Jan - 3 Jan 2025
La Casita: A Cozy Retreat Near Wake Forest University"

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$703
includes taxes & fees
12 Jan - 13 Jan 2025
Hartman Casita! Quiet neighborhood.1 king Bed!

Charming Winston-Salem Studio on Miller Park!

9.6 out of 10, Exceptional, (14)
"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$323
includes taxes & fees
6 Jan - 7 Jan 2025
Charming Winston-Salem Studio on Miller Park!

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

3 bedrooms 7min from downtown, college and hospital

10.0 out of 10, Exceptional, (1)
"We will only rent thru virbo, other company’s can’t compare. You can always tell when you open the door. Immaculate… would stay again definitely and probably as we travel. Thank you owner for letting us in your home. Nice and helpful neighbors…. Don’t even hesitate staying here. Orlando"
The price is NZ$338
includes taxes & fees
28 Dec - 29 Dec
3 bedrooms 7min from downtown, college and hospital

Historic West End Hideaway, walk to downtown WS

10.0 out of 10, Exceptional, (14)
"Convenient and spacious! Communication was outstanding. Would definitely book again. "
Historic West End Hideaway, walk to downtown WS

Charming Remodeled 4 Bedroom Home in Downtown High Point

10.0 out of 10, Exceptional, (63)
"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$257
includes taxes & fees
27 Dec - 28 Dec
Beautiful apt Downtown perfect for long term stays

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

9.8 out of 10, Exceptional, (101)
"My family and I had a nice stay at “The Lakeview House” this past weekend! Alfred is an awesome host with great communication. He wants his guest to know his availability and willingness to help make their stay better wonderful! "
The Lakeview House - access to pier/dock, fire pit and lake access

Newly renovated home away from home downtown High Point.

10.0 out of 10, Exceptional, (61)
"This home is amazing. Beautiful, clean, and spacious. Every detail was covered. Easy check in. We were here for a girls getaway weekend and we celebrated a 40th birthday. We couldn't have been more pleased. It was 4 of us and we were impressed with the decor of the home. Only problem was the guess bathrooms had low water pressure for hot water. We managed and the master bathroom had a beautiful shower that was great. I would love to stay here again. "
The price is NZ$407
includes taxes & fees
29 Dec - 30 Dec
Newly renovated home away from home downtown High Point.

Cottage at Lake Jeanette - 2 min from Greensboro Science Center

9.8 out of 10, Exceptional, (48)
"We came into town for a family gathering in Stokesdale. We had our grandkids, dogs, and my brother and sister-in-law. The house was perfect. It had plenty of room to spread out and the fenced in back yard was perfect for the dogs. I would highly recommend this house."
Cottage at Lake Jeanette - 2 min from Greensboro Science Center

The Farmhouse Retreat near Furniture Mkt and HPU

9.6 out of 10, Exceptional, (37)
"Property looked exactly like the pictures online. Very great location for the High Point market."
The price is NZ$575
includes taxes & fees
12 Jan - 13 Jan 2025
The Farmhouse Retreat near Furniture Mkt and HPU

⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close

9.8 out of 10, Exceptional, (39)
"My family and I stayed in the home over Thanksgiving and appreciated the fenced yard for our fur babies and a well-stocked kitchen for preparing meals. The beds are comfy and great water pressure in the showers. Everything we needed for our family gathering! Recommend! "
⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close

Hot Tub Heated NOW Salt Pool Private Resort Stay Mins to HPU & DT Furniture Mkt

9.4 out of 10, Exceptional, (18)
"We had a great time. Very nice place."
Hot Tub Heated NOW Salt Pool Private Resort Stay Mins to HPU & DT Furniture Mkt
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, (1000)
"The lady at reception was vrry nice and welcoming "
The price is NZ$134
includes taxes & fees
29 Dec - 30 Dec
Best Western Plus University Inn

Hawthorne Inn and Conference Center

3.0 star property
8.0 out of 10, Very good, (1001)
"Great place to stay.warm, friendly staff. Clean and spacious room. Conveniently downtown."
The price is NZ$151
includes taxes & fees
27 Dec - 28 Dec
Hawthorne Inn and Conference Center

La Quinta Inn & Suites by Wyndham Winston-Salem

2.5 star property
7.0 out of 10, Good, (1004)
"Every time I stay here it has always been a good experience "
The price is NZ$128
includes taxes & fees
30 Dec - 31 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.

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 167 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.