Holiday Homes in Winston-Salem

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Winston-Salem holiday homes

Fridge, microwave, oven, stovetop

Chic 2BR/2BA Near Dining & Shops

Chic 2BR/2BA Near Dining & Shops
2.0 star property
Winston-Salem
9.0 out of 10, Wonderful, (4 reviews)
"This house is really fantastic- we had a great stay. Cozy with a great kitchen - ideal location walking distance to several wonderful local establishments with great food options - super nice bathrooms and seriously good space in the bedrooms. We look forward to staying again. "
United States
John L.
The price is €223
includes taxes & fees
18 Jan - 19 Jan
Chic 2BR/2BA Near Dining & Shops
Dining

Downtown Charm, 3 Bdr, Near Rest and Bars

Downtown Charm, 3 Bdr, Near Rest and Bars
Winston-Salem
9.4 out of 10, Exceptional, (20 reviews)
"Wonderful place to stay…ecotourism need!"
United Kingdom
Patricia K.
The price is €214
includes taxes & fees
18 Jan - 19 Jan
Downtown Charm, 3 Bdr, Near Rest and Bars
Fridge, microwave, dishwasher, ice maker

Minimalist Stay

Minimalist Stay
Winston-Salem
10.0 out of 10, Exceptional, (4 reviews)
"Wonderful stay…just what we needed "
United States
Patricia K.
The price is €158
includes taxes & fees
20 Jan - 21 Jan
Minimalist Stay
Interior

Cozy Stay Near DT w/Deck and Fenced Yard

Cozy Stay Near DT w/Deck and Fenced Yard
Winston-Salem
8.0 out of 10, Very good, (2 reviews)
"Clean, quiwt, and close to everything. "
United States
Rebecca G.
The price is €148
includes taxes & fees
16 Jan - 17 Jan
Cozy Stay Near DT w/Deck and Fenced Yard
Exterior

Cozy Winston-Salem Vacation Cabin

Cozy Winston-Salem Vacation Cabin
2.0 star property
Winston-Salem
8.4 out of 10, Very good, (5 reviews)
"Host was prompt with responses and willing to assist. Sleeping for 10 or 12 if required but semi-comfortable seating for maybe 4 people unless you count dining room seating. Water pressure very low. Outdoor area and deck had nice view but old and could use some TLC with a covered are for rain days. We left a day early and went to a hotel."
Canada
John C.
Cozy Winston-Salem Vacation Cabin
Bar (on property)

Vintage Modern Synthesis in the Heart of Winston-Salem

Vintage Modern Synthesis in the Heart of Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (42 reviews)
"Great property, great location and very helpful owners"
United States
Simon P.
The price is €239
includes taxes & fees
20 Jan - 21 Jan
Vintage Modern Synthesis in the Heart of Winston-Salem
Microwave, oven, stovetop, dishwasher

Rosewood Loft I Upper Suite

Rosewood Loft I Upper Suite
Winston-Salem
10.0 out of 10, Exceptional, (1 review)
"The host was very easy to contact. The space was clean and it was very easy to find things that we needed. We really appreciated the necessities towel bundle. The space felt welcoming and comfortable."
United States
Delores C.
Rosewood Loft I Upper Suite
Fridge, microwave, oven, stovetop

Cozy 3BR Home Near Fairgrounds and Downtown

Cozy 3BR Home Near Fairgrounds and Downtown
2.0 star property
Winston-Salem
The price is €204
includes taxes & fees
20 Jan - 21 Jan
Cozy 3BR Home Near Fairgrounds and Downtown
TV, offices

Modern 2BR near WFU Steps to LJVM Coliseum Family-Friendly & Fast WiFi

Modern 2BR near WFU Steps to LJVM Coliseum Family-Friendly & Fast WiFi
2.0 star property
Winston-Salem
The price is €287
includes taxes & fees
18 Jan - 19 Jan
Modern 2BR near WFU Steps to LJVM Coliseum Family-Friendly & Fast WiFi
Terrace/patio

Cozy 2-bedroom bungalow in lovely Winston-Salem

Cozy 2-bedroom bungalow in lovely Winston-Salem
Winston-Salem
9.8 out of 10, Exceptional, (17 reviews)
"Perfect location and will definitely stay there again. Host answered questions promptly."
United States
Donna B.
The price is €225
includes taxes & fees
22 Jan - 23 Jan
Cozy 2-bedroom bungalow in lovely Winston-Salem
Smart TV, books

Three bedroom 5 minutes to state university & town, 10 min to baptist hospital

Three bedroom 5 minutes to state university & town, 10 min to baptist hospital
Winston-Salem
8.4 out of 10, Very good, (15 reviews)
"Great stay with family. "
United States
Tyler J.
The price is €189
includes taxes & fees
19 Jan - 20 Jan
Three bedroom 5 minutes to state university & town, 10 min to baptist hospital
Interior

Urban Escape 3 Bed 2.5 Bath Near Wake Forest

Urban Escape 3 Bed 2.5 Bath Near Wake Forest
Winston-Salem
9.2 out of 10, Wonderful, (9 reviews)
"An outstanding property.Well-appointed, clean, convenient to everything, and most importantly, quiet and peacefulWe are definitely staying again."
United States
Robert B.
Urban Escape 3 Bed 2.5 Bath Near Wake Forest
Exterior

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Winston-Salem
9.6 out of 10, Exceptional, (18 reviews)
"Wonderful stay! "
United States
Hannah J.
The price is €212
includes taxes & fees
16 Jan - 17 Jan
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Fridge, microwave, oven, stovetop

La Casita: A Cozy Retreat Near Wake Forest University"

La Casita: A Cozy Retreat Near Wake Forest University"
Winston-Salem
9.6 out of 10, Exceptional, (51 reviews)
"Great location. Clean and well equipped, will stay here again!"
United States
Greg S.
La Casita: A Cozy Retreat Near Wake Forest University"
Terrace/patio

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

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
Winston-Salem
10.0 out of 10, Exceptional, (50 reviews)
"We had a very relaxing stay here. The hot tub was lovely and the property was very close to a lot of shopping/restaurants. "
United States
Taylor E.
The price is €237
includes taxes & fees
18 Jan - 19 Jan
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
Private kitchen

La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA

La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
2.0 star property
Winston-Salem
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
Fridge, microwave, oven, stovetop

Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown

Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Winston-Salem
9.6 out of 10, Exceptional, (9 reviews)
"Nice location "
United States
Benelli T.
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Fridge, microwave, oven, stovetop

Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
10.0 out of 10, Exceptional, (22 reviews)
"We enjoyed our stay at the house.Found the house to be very clean and well stocked.The area was quiet and plenty of parking for us.Definitely a good value."
United States
gary e.
The price is €229
includes taxes & fees
11 Feb - 12 Feb
Quiet, newly renovated. Near everything!
Microwave, oven, stovetop, dishwasher

Soothing 3-bedroom house with AC in Winston-Salem close to highway restaurants

Soothing 3-bedroom house with AC in Winston-Salem close to highway restaurants
Winston-Salem
10.0 out of 10, Exceptional, (1 review)
"Very nice host with a nice welcoming home. The house is located in a area where it is easy to hit the heart of winston salem and get good food, have fun and enjoy your stay! "
United States
Joseph G.
The price is €310
includes taxes & fees
26 Jan - 27 Jan
Soothing 3-bedroom house with AC in Winston-Salem close to highway restaurants
Exterior

5 mins to downtown 3 Kings Old Salem Sanctuary

5 mins to downtown 3 Kings Old Salem Sanctuary
2.0 star property
Winston-Salem
5 mins to downtown 3 Kings Old Salem Sanctuary
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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Top Winston-Salem Hotel Reviews

Sleep Inn Hanes Mall

Sleep Inn Hanes Mall

10/10 Excellent
"Good breakfast if need anything they were right there. It’s well kept meaning very clean. No complains here I was there from January 9th 2026 til January 11 2026 we’ll be back soon "
Starr 2-night trip
Posted 3 days ago
Sleep Inn Hanes Mall

Find out more about Winston-Salem

Winston-Salem Holiday Homes information

Number of reviews
261
Accommodation
180 Holiday Homes
Lowest Price
€148
Highest Price
€310