Holiday Homes in Winston - Salem

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Featured Holiday Homes in Winston - Salem

Barn Loft with Mountain Views, minutes from Hanging Rock State Park

10.0 out of 10, Exceptional, (107)
"The stay here was wonderful. Laurel was great at getting us setup for the stay, prompt in responding to questions and very detailed with instructions & helpful tips. The location was quaint and cozy. It has a great view of mountain foliage in the day. It also is a perfect place for stargazing at night. It was perfect for our weekend getaway! ThThe location has "
Barn Loft with Mountain Views, minutes from Hanging Rock State Park

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 AU$187
includes taxes & fees
25 Nov - 26 Nov
The Cook's Wall Cabin

Deacon Stays: The Cottage - Walk to WFU

10.0 out of 10, Exceptional, (13)
"I was pleasantly suprised by this place, the location was close to anything you need, and the house itself was perfect! Super clean, all the latest tech, huge tv, surround speakers throughout! Great spot, will certainly return! Why pay $450 a night for a hotel suite, when you can stay here in a house all to yourself!!"
Deacon Stays: The Cottage - Walk to WFU

Quiet, newly renovated. Near everything!

9.6 out of 10, Exceptional, (4)
"The duplex is charming and comfortable. There isn’t really a yard to take pets out in, you have to walk down the street to a green area. The host is extremely quick to respond. Amazing supply of everything you can think of to make your stay an easy one. Highly recommend"
The price is AU$413
includes taxes & fees
25 Nov - 26 Nov
Quiet, newly renovated. Near everything!

Pinnacle Cottage - 2 bedroom/1.5 bath - near Pilot Mountain State Park

10.0 out of 10, Exceptional, (20)
"The home is so inviting and comfortable. It is convenient to Pilot Mountain (you can see it from the front door) and hiking trails! There are plenty of good restaurants nearby. My wife and I found it to be a great get away and hope to return soon. "
Pinnacle Cottage - 2 bedroom/1.5 bath - near Pilot Mountain State Park

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

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

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 AU$353
includes taxes & fees
25 Nov - 26 Nov
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

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 AU$634
includes taxes & fees
26 Nov - 27 Nov
The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!

The Charming Getaway

10.0 out of 10, Exceptional, (12)
"The house was beautiful and easy to find. We really enjoyed our stay as it felt like home. I highly recommend this home."
The Charming Getaway

Spacious Salem-Winston Home w/ Deck!

9.8 out of 10, Exceptional, (8)
"We came together at Winston Salem since our daughter is attending g a local college there. Cole was wonderful with communicating with us and quick to reply with any questions we had. My aunt forgot several things at the house and he even went out of his way to ship them back home to her. The house is beautiful and stocked with comforts of home. They allowed us to have our two dogs with us so we truly felt like the whole family was all together. The only real downfall was that we didn’t realize...
Spacious Salem-Winston Home w/ Deck!

Cozy and Peaceful Tiny House on a 100-acre Farm

10.0 out of 10, Exceptional, (14)
"We had a great time visiting with the goats and chickens. The tiny house was very cute with everything we needed. The location was so peaceful!"
Cozy and Peaceful Tiny House on a 100-acre Farm

Mins from PTI Airport/Triad Park/market

9.6 out of 10, Exceptional, (7)
"We moved our daughter in for senior year at Highpoint University and this was located about 15 minutes away. It was clean. It was comfortable. The beds are amazing, we slept great! The owner was excellent with communication. "
Mins from PTI Airport/Triad Park/market

Sunlight facing entire Townhome with 2 BR & 2.5 Bath

8.4 out of 10, Very good, (11)
"Overall this wasn’t a bad place. Communication was great. You have to use your own login to watch Netflix etc. Bathrooms needed to be cleaned a bit better due to hair, dirt rings in the tub and where the soap bottles were. Just needs a few tweaks."
Sunlight facing entire Townhome with 2 BR & 2.5 Bath

Comfortable, covenient, quaint

10.0 out of 10, Exceptional, (18)
"Absolute excellent location and peaceful just what this exhausted mother needed! Thank you!"
Comfortable, covenient, quaint

Updated 1BR cottage on private acre+ lot

10.0 out of 10, Exceptional, (3)
"The place was supuer nice and clean! "
The price is AU$260
includes taxes & fees
9 Dec - 10 Dec
Updated 1BR cottage on private acre+ lot

Carolina Cheerful and Charming

9.6 out of 10, Exceptional, (5)
"This was a great little house convenient to all that we were doing in town. I was there for the ardmore artwork and we like visiting Old Salem and downtown. Very walkable area but several loose dogs which was scary with our dog. I understand the property owner can not control this but it was quite a problem a few times."
Carolina Cheerful and Charming

Treetop - 3 King Suites- sister property next door #1559015

10.0 out of 10, Exceptional, (12)
"This home was perfect location for my family to stay during the wedding of my niece at Nana-Mac’s Meadow. Being able to have a place to rest after rehearsal and the wedding on Saturday we great. The bed are so comfortable and eveyone rested great both nights. We loved everything about the home. The little personal touches by the owner meant a lot. Although we didn’t have time to enjoy the firepit it was nice that the owner made sure wood was available upon our arrival. It was like home away...
The price is AU$895
includes taxes & fees
2 Dec - 3 Dec
Treetop - 3 King Suites- sister property next door #1559015

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

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 AU$599
includes taxes & fees
25 Nov - 26 Nov
Secluded close to everything!
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 property types in Winston - Salem

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 AU$187
includes taxes & fees
25 Nov - 26 Nov
The Cook's Wall Cabin

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 AU$420
includes taxes & fees
25 Nov - 26 Nov
The Red Door Cabin

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 AU$318
includes taxes & fees
25 Nov - 26 Nov
Quaint 2 bed 1 bath cottage style home
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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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.