Holiday Homes in Winston-Salem

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 June - 14 June
In three months
10 July - 12 July
In four months
7 Aug - 9 Aug

Our top choices for Winston-Salem holiday homes

Fridge, microwave, oven, stovetop

Updated 1BR cottage on private acre+ lot

Updated 1BR cottage on private acre+ lot
Winston-Salem
10.0 out of 10, Exceptional, (21 reviews)
"Such a great place to stay. Everything we needed, we had. I would highly recommend this and would stay again. "
United States
Zack W.
The price is AU$201
includes taxes & fees
29 Apr - 30 Apr
Updated 1BR cottage on private acre+ lot
Smart TV, fireplace

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

The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!
Winston-Salem
9.8 out of 10, Exceptional, (36 reviews)
"Perfect size, very clean and great location!"
United States
Laron A.
The price is AU$730
includes taxes & fees
4 May - 5 May
The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!
2 bedrooms, iron/ironing board, WiFi, bed sheets

Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds

Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds
Winston-Salem
10.0 out of 10, Exceptional, (1 review)
The price is AU$356
includes taxes & fees
30 Apr - 1 May
Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds
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
9.8 out of 10, Exceptional, (51 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 AU$385
includes taxes & fees
20 Apr - 21 Apr
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
Fridge, microwave, oven, stovetop

Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
10.0 out of 10, Exceptional, (24 reviews)
"The property was clean, and comfortable in a nice neighborhood close to amenities."
United States
Maria H.
The price is AU$375
includes taxes & fees
20 Apr - 21 Apr
Quiet, newly renovated. Near everything!
Interior

Hartman Casita! Quiet neighborhood.1 king Bed!

Hartman Casita! Quiet neighborhood.1 king Bed!
Winston-Salem
9.8 out of 10, Exceptional, (20 reviews)
"The house was just what we need in terms of travel time to our event, comfort and peace! Would definitely recommend and stay again! "
United States
Stefanie H.
The price is AU$701
includes taxes & fees
4 May - 5 May
Hartman Casita! Quiet neighborhood.1 king Bed!
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
Winston-Salem
The price is AU$294
includes taxes & fees
20 Apr - 21 Apr
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
Interior

Rosewood Loft I Lower Suite

Rosewood Loft I Lower Suite
Winston-Salem
The price is AU$322
includes taxes & fees
16 Apr - 17 Apr
Rosewood Loft I Lower Suite
TV

Chic 2BR/2BA Near Dining & Shops

Chic 2BR/2BA Near Dining & Shops
Winston-Salem
9.6 out of 10, Exceptional, (7 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 AU$364
includes taxes & fees
16 Apr - 17 Apr
Chic 2BR/2BA Near Dining & Shops
Interior

Cozy Stay Near DT w/Deck and Fenced Yard

Cozy Stay Near DT w/Deck and Fenced Yard
Winston-Salem
9.4 out of 10, Exceptional, (6 reviews)
"Clean, quiwt, and close to everything. "
United States
Rebecca G.
The price is AU$251
includes taxes & fees
16 Apr - 17 Apr
Cozy Stay Near DT w/Deck and Fenced Yard
Outdoor dining

La Casita .

La Casita .
Winston-Salem
10.0 out of 10, Exceptional, (3 reviews)
"Overall a great place to stay. Super cozy! "
United States
Darren L.
The price is AU$267
includes taxes & fees
16 Apr - 17 Apr
La Casita .
Fridge, microwave, oven, stovetop

Cozy 3BR Home Near Fairgrounds and Downtown

Cozy 3BR Home Near Fairgrounds and Downtown
Winston-Salem
The price is AU$342
includes taxes & fees
4 May - 5 May
Cozy 3BR Home Near Fairgrounds and Downtown
Smart TV, books

High Ceilings | King Beds | 85” TV | Near Downtown

High Ceilings | King Beds | 85” TV | Near Downtown
Winston-Salem
7.6 out of 10, Good, (15 reviews)
"Lovely and affordable apartment with incredibly attentive and responsive host. Would totally stay again!"
United States
Caleb W.
The price is AU$345
includes taxes & fees
20 Apr - 21 Apr
High Ceilings | King Beds | 85” TV | Near Downtown
Living area

4 Beds | King | 85” TV | 5min to WSSU & Downtown

4 Beds | King | 85” TV | 5min to WSSU & Downtown
Winston-Salem
9.0 out of 10, Wonderful, (4 reviews)
"We enjoyed our short stay, house is very cute and cozy and well put together "
United States
Anonymous traveller
The price is AU$360
includes taxes & fees
29 Apr - 30 Apr
4 Beds | King | 85” TV | 5min to WSSU & Downtown
Terrace/patio

Luxury 3BR Townhome - Sleep 6

Luxury 3BR Townhome - Sleep 6
Winston-Salem
9.2 out of 10, Wonderful, (46 reviews)
"Excellent amenities. Very clean and we had wonderful stay. "
United States
Akiko C.
Luxury 3BR Townhome - Sleep 6
Exterior

Cozy Winston-Salem Vacation Cabin

Cozy Winston-Salem Vacation Cabin
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.
The price is AU$641
includes taxes & fees
28 Apr - 29 Apr
Cozy Winston-Salem Vacation Cabin
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 AU$339
includes taxes & fees
16 Apr - 17 Apr
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Fridge, microwave, oven, stovetop

New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University

New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
Winston-Salem
10.0 out of 10, Exceptional, (2 reviews)
"We thoroughly enjoyed our stay; very nicely furnished, bed was comfortable and it was very clean and inviting, would not hesitate to rent again in the future"
United States
Catherine D.
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
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)
"We were there for a conference, so this location is ideal! So close to the convention center, comfortable, clean and spacious. We loved it!"
United States
Terrie H.
The price is AU$442
includes taxes & fees
19 Apr - 20 Apr
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
TV, video games

Spacious Historical Home 3 mins from Downtown

Spacious Historical Home 3 mins from Downtown
Winston-Salem
The price is AU$573
includes taxes & fees
20 Apr - 21 Apr
Spacious Historical Home 3 mins from Downtown
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

Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

8/10 Good
"Great location to the university. Staff was very accommodating. "
Mary 1-night trip
Posted 2 hours ago
Hawthorne Inn and Conference Center

Find out more about Winston-Salem

Winston-Salem Holiday Homes information

Number of reviews
187
Accommodation
185 Holiday Homes
Lowest Price
AU$201
Highest Price
AU$730