Winston-Salem Holiday Rentals

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Holiday Rentals in Winston-Salem

Private kitchen
Cozy Townhome in a Great Location
10.0 out of 10, Exceptional, (7)
"👍"
Cozy Townhome in a Great Location
Smart TV, fireplace
The Red Door Cabin
10.0 out of 10, Exceptional, (5)
"Serenity without isolation"
The price is HK$1,351
HK$2,250 total
includes taxes & fees
20 May - 21 May
The Red Door Cabin
Fridge, microwave, oven, stovetop
Hartman Casita! Quiet neighborhood.1 king Bed!
10.0 out of 10, Exceptional, (10)
"It was a wonderful few days, we watched my grandson play soccer at truist park and had enough time to play some corn hole at the property. excellent location and the house was spotless."
The price is HK$1,366
HK$3,375 total
includes taxes & fees
5 Jun - 6 Jun
Hartman Casita! Quiet neighborhood.1 king Bed!
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Fridge, microwave, oven, stovetop
Historic West End Hideaway, walk to downtown WS
10.0 out of 10, Exceptional, (11)
"We had a fantastic stay in this beautiful home. Super well equipped, comfortable beds and linens, spotless clean. Our host was amazing at communicating making sure the information for check in, our stay, and check out was always at our fingertips. Highly recommend this property for anyone visiting Winston-Salem. We will be booking this same location for the next time we visit that’s for sure!"
Historic West End Hideaway, walk to downtown WS
Property grounds
Arbor Lane Cabin - authentic & charming tucked away cabin, yet near it all.
10.0 out of 10, Exceptional, (253)
"If you are looking peace and quite this is the place nice cabin little ways off the road no neighbors no cars passing by private only 5 minutes to town for whatever you need would stay again"
Arbor Lane Cabin - authentic & charming tucked away cabin, yet near it all.
Property grounds
Barn Loft with Mountain Views, minutes from Hanging Rock State Park
10.0 out of 10, Exceptional, (86)
"The property is beautiful. I went for a self-care long weekend on my own. The space is comfortable and perfect for a easy get away in nature. I spent more of my time sitting on the porch, than inside. The property is rural, but doesn't feel completely disconnected. Close to 2 great hiking parks. Laurel was attentive and had the place stocked with the necessities and then some."
Barn Loft with Mountain Views, minutes from Hanging Rock State Park
Fridge, microwave, stovetop, dishwasher
Updated High Point Retreat w/ Pool & Backyard
10.0 out of 10, Exceptional, (8)
"One of the best vacation rentals you can bring pets to that we’ve ever stayed in! Hosts are super responsive and they went above and beyond to make us feel at home! We hope to stay here again when we are back in the area. Easy check in and out & great communication. Home is cozy and well stocked with items you need in the kitchen. We didn’t get to utilize the pool due to rain and length of stay but it is large and well kept, added bonus is a lovely backyard for the fur babies to run and play in....
Updated High Point Retreat w/ Pool & Backyard
Exterior
North Carolina Retreat - Deck, Grills & Lake Views
10.0 out of 10, Exceptional, (15)
"Good location and fit for graduation. Well stocked kitchen."
North Carolina Retreat - Deck, Grills & Lake Views
Dining tables
⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close
10.0 out of 10, Exceptional, (29)
"The property was very clean and more! Easy access from our destination and shopping and groceries was close. Never had any issues, property owner is always available to answer questions and help. Our dogs loved the back yard and room to play. Privacy was awesome and neighborhood quiet. Loved all the extras the owners left for us to enjoy!"
⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close
Smart TV
Cozy Home in Central Location, Gboro & High Point!
10.0 out of 10, Exceptional, (28)
"This is such a cute house that is so conveniently located to downtown Greensboro. The house was very clean and had everything you could need to have a fabulous, fun weekend with friends!"
The price is HK$937
HK$2,113 total
includes taxes & fees
19 May - 20 May
Cozy Home in Central Location, Gboro & High Point!
Property grounds
Pfafftown Home ~ 7 Mi to Wake Forest University!
10.0 out of 10, Exceptional, (3)
"beautiful house and yard. it was plenty spacious and we had plenty of room for everyone to do tbeir thing without bothering others. the kitchen wasnt stocked well though. there was only 2 coffee cups."
Pfafftown Home ~ 7 Mi to Wake Forest University!
Pool
Lakefront Home with Saltwater Pool, Hot Tub, Firepit, Kayaks. Pet Friendly
10.0 out of 10, Exceptional, (24)
"They had great cookware in the kitchen and we're very helpful. Seems to be honest and sincere as hosts. They describe the property pretty accurately."
Lakefront Home with Saltwater Pool, Hot Tub, Firepit, Kayaks. Pet Friendly
Interior
Remodeled historic home! Steps away from dining & shops - Easy walk to Old Salem
9.8 out of 10, Exceptional, (35)
"Love the location and it was absolutely spotless! One small note: the sofa shown is not a sleeper sofa, there’s a futon."
Remodeled historic home! Steps away from dining & shops - Easy walk to Old Salem
Exterior
The Lakeview House - access to pier/dock, fire pit and lake access
9.8 out of 10, Exceptional, (93)
"We’ve stayed many times at this home. Always excellent."
The Lakeview House - access to pier/dock, fire pit and lake access
Property grounds
Waterfront Bungalow with private pier and fire pit on High Rock lake
9.8 out of 10, Exceptional, (49)
"Beautiful property on high rock Lake that was meticulously maintained and accommodating. Alfred made our stay over the top by his attentiveness and attention to our needs of any kind! The house was plenty ice and well equipped, and there was plenty of parking as well as additional parking offered. I would stay there again anytime and likely will book another weekend soon."
Waterfront Bungalow with private pier and fire pit on High Rock lake
Property grounds
Cozy home! established neighborhood. Entire house.
9.8 out of 10, Exceptional, (30)
"This is my family’s second time staying at this property. It is quite roomy for 6-8 guests and has everything you need to feel at home. The neighborhood is lovely and close to everything in the Greensboro area. Both John and Miranda are amazing and super reachable. We will definitely stay here again!"
The price is HK$1,288
HK$3,294 total
includes taxes & fees
19 May - 20 May
Cozy home! established neighborhood. Entire house.
Property grounds
The Cook's Wall Cabin
9.8 out of 10, Exceptional, (69)
"We love this place! Peaceful, immaculate, safe, comfortable, and quiet would definitely be descriptors. The host was friendly and welcoming, despite our late arrival. The clear night sky was spectacular, and the view of Cook's Wall was beautiful. This is a place you will wish you could stay longer!!"
The price is HK$718
HK$934 total
includes taxes & fees
19 May - 20 May
The Cook's Wall Cabin
Property grounds
Lakefront/Boat Dock, 3/2, Furnished, Castaway Cottage, covered back deck views
9.8 out of 10, Exceptional, (116)
"This was our second stay at Castaway Cottage. Lovely view of the lake in a rural, quiet subdivision. Our hosts, as always, attentive and accommodating. If you like getting up in the morning, relaxing with a cup of coffee and watching water-birds on the lake, this is the location for you."
Lakefront/Boat Dock, 3/2, Furnished, Castaway Cottage, covered back deck views
Outdoor pool, a heated pool
Hot Tub Heated NOW Salt Pool Private Resort Stay Mins to HPU & DT Furniture Mkt
9.8 out of 10, Exceptional, (14)
"Nice, quiet neighborhood. Host was excellent communicator"
Hot Tub Heated NOW Salt Pool Private Resort Stay Mins to HPU & DT Furniture Mkt
Fridge, microwave, stovetop, dishwasher
Bright Greensboro Escape ~ 1 Mi to Downtown
9.6 out of 10, Exceptional, (22)
"I stayed with my son at this property for a week while he swam at the Nationals Swim Meet at the Greensboro swim coliseum. The property was perfect for us--a 10 minute drive from the venue, but in an established, safe neighborhood surrounded by beautiful trees and plentiful walking paths. It is walkable to great local restaurants and coffee shops, and a short drive to great shopping, dining, grocery stores (Trader Joe's, Whole Foods, etc.). Highly recommend. We'll definitely be back!!"
Bright Greensboro Escape ~ 1 Mi to Downtown
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See all available properties in 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.

Other types of properties in Winston-Salem you may be interested in

Exterior
Comfort Suites Hanes Mall
2.5 star property
8.6 out of 10, Excellent, (1002)
"Staff was helpful and very easy to talk to. My check in was smooth and easy. "
The price is HK$757
HK$871 total
includes taxes & fees
21 May - 22 May
Comfort Suites Hanes Mall
Reception
DoubleTree by Hilton Winston Salem - University
4.0 star property
8.2 out of 10, Very good, (1001)
"M"
The price is HK$796
HK$899 total
includes taxes & fees
9 Jun - 10 Jun
DoubleTree by Hilton Winston Salem - University
Lobby
Best Western Plus University Inn
3.5 star property
7.8 out of 10, Good, (897)
"It seemed the overall building is in need of updating. The breakfast area and the breakfast itself were wonderful. "
The price is HK$524
HK$592 total
includes taxes & fees
21 May - 22 May
Best Western Plus University Inn
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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Frequently asked questions

Can I find holiday rentals in Winston-Salem?

Yes, there are holiday rentals in Winston-Salem close to Forest Hills, 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.

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

Choose from 146 Expedia holiday rentals in Winston-Salem for a memorable holiday.

What can I see and do in Winston-Salem?

Forest Hills and Airbound Trampoline Park are a couple of the family-friendly sights, whereas cultural attractions include Old Salem and Theatre Alliance. 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.

Recent reviews of Winston-Salem properties
Expedia verified reviews

The Historic Brookstown Inn, Trademark Collection by Wyndham

The Historic Brookstown Inn, Trademark Collection by Wyndham

5/5 Excellent
"Beautiful historic hotel, staff was friendly and helpful, clean and comfy"
A verified traveller stayed at The Historic Brookstown Inn, Trademark Collection by Wyndham
Posted 1 day ago
The Historic Brookstown Inn, Trademark Collection by Wyndham