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, (25)
"great spot to stay for a getaway. Hot tub, heat lamps, grill all worked well. Place had plenty of dog amenities. Could use a kitchen restock "
The price is NZ$407
includes taxes & fees
3 Feb - 4 Feb
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

Cozy guest suite in Winston Salem

9.4 out of 10, Exceptional, (106)
"Fine stay"
Cozy guest suite in Winston Salem

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$359
includes taxes & fees
3 Feb - 4 Feb
3 bedrooms 7min from downtown, college and hospital

The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!

10.0 out of 10, Exceptional, (21)
"This is house is amazing, it was perfect. Initially, it was supposed to be for just four ladies we ended up growing to eight ladies. This house was ample space and had everything we needed. The host Lina was responsive and quite accommodating when an early arrival was needed. I meet up with my friends annually in this area, we will definitely book this property again. It has all the comforts of home. "
The price is NZ$684
includes taxes & fees
4 Feb - 5 Feb
The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!

Cozy Townhome in a Great Location

9.8 out of 10, Exceptional, (21)
"My family and I spent Christmas in a stranger’s home but it never felt unfamiliar. This house felt like home. We thank you for allowing us to stay in your home for the holidays."
Cozy Townhome in a Great Location

Cozy Winston-Salem Vacation Cabin

2.0 star property
10.0 out of 10, Exceptional, (1)
"We rented the property for our O40 soccer team for a tourney in Winston. It had plenty of room for the crew with lots of beds. The location was good with a nice wooded backyard. The house was fine, but could use some updating and probably a bit more seating options in the living room and king suite upstairs. Also, sponges or scrubbies in the kitchen would have been nice. All in all, though, it served the purpose and was a great house for our needs. Juan was really responsive and a great host."
The price is NZ$862
includes taxes & fees
3 Feb - 4 Feb
Cozy Winston-Salem Vacation Cabin

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$363
includes taxes & fees
3 Feb - 4 Feb
High ceiling house close to downtown

The Hot Tub Hideaway

9.8 out of 10, Exceptional, (12)
"Wonderful, private tiny house"
The price is NZ$477
includes taxes & fees
31 Jan - 1 Feb
The Hot Tub Hideaway

Luxury 3BR Townhome - Sleep 6

8.8 out of 10, Excellent, (22)
"Very clean and well maintained. Would definitely stay here again. "
The price is NZ$454
includes taxes & fees
2 Feb - 3 Feb
Luxury 3BR Townhome - Sleep 6

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$495
includes taxes & fees
7 Feb - 8 Feb
La Casita: A Cozy Retreat Near Wake Forest University"

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

10.0 out of 10, Exceptional, (49)
"This property is lovely, clean, and spacious. This was our second stay and will definitely return."
Remodeled historic home! Steps away from dining & shops - Easy walk to Old Salem

The Red Door Cabin

10.0 out of 10, Exceptional, (10)
"Very clean and very comfortable"
The price is NZ$477
includes taxes & fees
2 Feb - 3 Feb
The Red Door Cabin

Entire Bungalow hosted by Medina

10.0 out of 10, Exceptional, (1)
"Had a great time and the owner was available for me whenever I needed. Will use as my place to stay when I come back"
Entire Bungalow hosted by Medina

Quiet, newly renovated. Near everything!

9.6 out of 10, Exceptional, (5)
"Wonderful property in a quiet, safe neighborhood within 10 minutes of almost everything in Winston-Salem. Good walking area (albeit hilly). Home was recently renovated with a very nice kitchen and bathrooms, one with a walk-in shower. Owner has stocked almost every amenity under the sun from K-Cups with creamer, sugar and Sweet and Low to wrapped toothbrushes and toothpaste, shampoo, body wash, and conditioner. Frequent travelers will even appreciate the high quality of the toilet paper...
The price is NZ$467
includes taxes & fees
2 Feb - 3 Feb
Quiet, newly renovated. Near everything!

Beautiful apt Downtown perfect for long term stays

8.4 out of 10, Very good, (26)
"The room was cute and clean. The plumbing in the bathroom was needing to be replaced but was functional. Overall it was fine for the couple of nights I was there.."
The price is NZ$257
includes taxes & fees
1 Feb - 2 Feb
Beautiful apt Downtown perfect for long term stays

The Farmhouse Retreat near Furniture Mkt and HPU

9.6 out of 10, Exceptional, (39)
"We came to watch our son play basketball for HPU. Couldn’t have asked for a better location to go back and forth (even walked a few times). Close to many amenities for groceries etc. We were able to do a load of laundry and the keyless entry made it easy for everyone to come and go. Totally coming back next year! "
The price is NZ$617
includes taxes & fees
5 Feb - 6 Feb
The Farmhouse Retreat near Furniture Mkt and HPU

Charming and Cozy Bedroom in Shared Home

10.0 out of 10, Exceptional, (3)
"host extremely responsive. possible pot linger odor. kit adequate. easy access to downtown greensboro."
The price is NZ$169
includes taxes & fees
31 Jan - 1 Feb
Charming and Cozy Bedroom in Shared Home

Beautiful, Spacious 4 Bedroom Home one Block from High Point University

2.0 star property
10.0 out of 10, Exceptional, (5)
"The home was very welcoming and friendly. The host was very quick to respond and make us feel welcome. Although we had a short stay, we enjoyed it very much. It had all the amenities we needed and if we are back in the area we will stay here again!"
The price is NZ$527
includes taxes & fees
2 Feb - 3 Feb
Beautiful, Spacious 4 Bedroom Home one Block from High Point University

Cottage at Lake Jeanette - 2 min from Greensboro Science Center

9.8 out of 10, Exceptional, (48)
"My husband and I (and our PomChi) travelled to Greensboro to visit family and celebrate the holidays early. The house is so much nicer in person- I didn’t realize how big it was. It’s in a great neighborhood close to everything. I felt very safe. My pup absolutely loved the huge fenced in backyard. Communication with our host was perfect. I can’t wait for our next trip - we loved this house."
Cottage at Lake Jeanette - 2 min from Greensboro Science Center

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
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
7.4 out of 10, Good, (1001)
"Breakfast is always good. This is our preferred hotel when we are in the Winston-Salem area. "
The price is NZ$134
includes taxes & fees
3 Feb - 4 Feb
Best Western Plus University Inn

Hawthorne Inn and Conference Center

3.0 star property
8.0 out of 10, Very good, (1005)
"4/5 would stay again "
The price is NZ$178
includes taxes & fees
3 Feb - 4 Feb
Hawthorne Inn and Conference Center

The Historic Brookstown Inn, Trademark Collection by Wyndham

3.5 star property
9.6 out of 10, Exceptional, (1004)
"This is a charming hotel. We went during the Christmas season and it was decorated so beautifully inside and out. We would definitely stay here again if we are in the area. "
The price is NZ$235
includes taxes & fees
9 Feb - 10 Feb
The Historic Brookstown Inn, Trademark Collection by Wyndham
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?

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!: This highly rated holiday home rental in Winston-Salem is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a selection of games and 1 hot tub. Other favourite homes for rent in Winston-Salem are 3 bedrooms 7min from downtown, college and hospital and Cozy Townhome in a Great Location.

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

Choose from 174 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.