Winston-Salem, North Carolina

Vacation Rentals in Winston-Salem, North Carolina

Discover 183 vacation rental properties in Winston-Salem. From 1 to 7 bedrooms. Average $180/night. 100% have pools.

183 verified listings Book securely on VRBO Prices updated March 2026

183 properties available

Stylish 1BR Apt w/KING Bed in Central Location

Stylish 1BR Apt w/KING Bed in Central Location

1 bed 1 bath
PoolA/CWiFiBalcony
$126/night
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Private & sweet patio level apartment in downtown Winston-Salem

Private & sweet patio level apartment in downtown Winston-Salem

2 beds 1 bath
PoolA/CWiFiBalcony
$117/night
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Cozy guest suite in Winston Salem

Cozy guest suite in Winston Salem

1 bed 1 bath
PoolA/CWiFiBalcony
$50/night
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Cozy! ~5 Min Walk to Hospital

Cozy! ~5 Min Walk to Hospital

1 bed 1 bath
PoolA/CWiFiBalcony
$95/night
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Winston-Salem's Man Cave

Winston-Salem's Man Cave

1 bed 1 bath
PoolA/CWiFiBalcony
$132/night
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Elegant Pet Friendly Ranch Home close to everything!

Elegant Pet Friendly Ranch Home close to everything!

2 beds 1 bath
PoolA/CWiFiBalcony
$211/night
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Quiet, home-style stay in historic Washington Park neighborhood.

Quiet, home-style stay in historic Washington Park neighborhood.

1 bed 1 bath
PoolA/CWiFiBalcony
$100/night
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Cozy Townhome in a Great Location

Cozy Townhome in a Great Location

3 beds 2 baths
PoolA/CWiFiBalcony
$100/night
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The Vista Studio-Close to Downtown Wake Forest Baptist Hospital

The Vista Studio-Close to Downtown Wake Forest Baptist Hospital

1 bed 1 bath
PoolA/CWiFiBalcony
$90/night
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An urban oasis in downtown Winston-Salem

An urban oasis in downtown Winston-Salem

2 beds 1 bath
PoolA/CWiFiBalcony
$117/night
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Captains Quarters - Historical Home Downtown Rental

Captains Quarters - Historical Home Downtown Rental

1 bed 1 bath
PoolA/CWiFiBalcony
$75/night
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Remodeled historic home! Steps away from dining & shops - Easy walk to Old Salem

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

2 beds 2 baths
PoolA/CWiFiBalcony
$175/night
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La Casita! near to WFU. Cozy house. 1 king bed

La Casita! near to WFU. Cozy house. 1 king bed

2 beds 1 bath
PoolA/CWiFiBalcony
$137/night
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The Red Door Cabin

The Red Door Cabin

1 bed 1 bath
PoolA/CWiFiBalcony
$187/night
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Beautiful 2BD Apt @ JamesWay in West End Area!

Beautiful 2BD Apt @ JamesWay in West End Area!

2 beds 1 bath
PoolA/CWiFiBalcony
$80/night
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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!

1 bed 1 bath
PoolA/CWiFiBalcony
$184/night
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Luxury 3BR Townhome - Sleep 6

Luxury 3BR Townhome - Sleep 6

3 beds 3 baths
PoolA/CWiFiBalcony
$126/night
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Vintage Modern Synthesis in the Heart of Winston-Salem

Vintage Modern Synthesis in the Heart of Winston-Salem

2 beds 1 bath
PoolA/CWiFiBalcony
$151/night
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Deacon Stays: The Cottage - Walk to WFU

Deacon Stays: The Cottage - Walk to WFU

2 beds 2 baths
PoolA/CWiFiBalcony
$177/night
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Comfortable, covenient, quaint

Comfortable, covenient, quaint

2 beds 2 baths
PoolA/CWiFiBalcony
$155/night
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Spacious 1BR w/ KING Bed Near Hospital & Downtown

Spacious 1BR w/ KING Bed Near Hospital & Downtown

1 bed 1 bath
PoolA/CWiFiBalcony
$126/night
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Adorable near UNCSA and Downtown

Adorable near UNCSA and Downtown

2 beds 2 baths
PoolA/CWiFiBalcony
$207/night
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Downtown Winston-Salem Condo w/ Private Library!

Downtown Winston-Salem Condo w/ Private Library!

2 beds 2 baths
PoolA/CWiFiBalcony
$268/night
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Mid-Century Modern Cottage in Ardmore Area!

Mid-Century Modern Cottage in Ardmore Area!

2 beds 1 bath
PoolA/CWiFiBalcony
$154/night
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Charming Winston-Salem Studio on Miller Park!

Charming Winston-Salem Studio on Miller Park!

1 bath
PoolA/CWiFiBalcony
$118/night
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Renovated Hidden Gem close to Kernersville

Renovated Hidden Gem close to Kernersville

3 beds 2 baths
PoolA/CWiFiBalcony
$179/night
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Winston-Salem Vacation Rental - Walk Downtown!

Winston-Salem Vacation Rental - Walk Downtown!

2 beds 2 baths
PoolA/CWiFiBalcony
$178/night
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Quiet 2 bed home close to hospitals & universities

Quiet 2 bed home close to hospitals & universities

2 beds 1 bath
PoolA/CWiFiBalcony
$90/night
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Freshly Renovated 1+ Bedroom in Great Downtown Location

Freshly Renovated 1+ Bedroom in Great Downtown Location

1 bed 1 bath
PoolA/CWiFiBalcony
$116/night
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The Blue Door Cabin

The Blue Door Cabin

1 bed 1 bath
PoolA/CWiFiBalcony
$160/night
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Classy Catch in Winston

Classy Catch in Winston

2 beds 1 bath
PoolA/CWiFiBalcony
$154/night
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Hidden GEM 1 king bed &2 queens

Hidden GEM 1 king bed &2 queens

3 beds 1 bath
PoolA/CWiFiBalcony
$116/night
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Single family home near Reynolda Village and Wake Forest University

Single family home near Reynolda Village and Wake Forest University

4 beds 3 baths
PoolA/CWiFiBalcony
$201/night
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Modern, Stylish near UNCSA and Downtown

Modern, Stylish near UNCSA and Downtown

2 beds 1 bath
PoolA/CWiFiBalcony
$151/night
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Upscale City Cottage Getaway

Upscale City Cottage Getaway

2 beds 1 bath
PoolA/CWiFiBalcony
$207/night
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Charming 2/2 condo near Wake Forest with full kitchen and strong Wi-Fi

Charming 2/2 condo near Wake Forest with full kitchen and strong Wi-Fi

2 beds 2 baths
PoolA/CWiFiBalcony
$165/night
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Modern 1BR Near WFU Hospital

Modern 1BR Near WFU Hospital

1 bed 1 bath
PoolA/CWiFiBalcony
$88/night
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Cozy & Clean Home In Ardmore - The Yellow Cottage

Cozy & Clean Home In Ardmore - The Yellow Cottage

1 bed 1 bath
PoolA/CWiFiBalcony
$108/night
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Discover Tranquility: Your Stylish Secret Mountain Retreat in Ardmore

Discover Tranquility: Your Stylish Secret Mountain Retreat in Ardmore

3 beds 2 baths
PoolA/CWiFiBalcony
$206/night
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Eclectic Winston-Salem Home: 3 Mi to Downtown!

Eclectic Winston-Salem Home: 3 Mi to Downtown!

2 beds 2 baths
PoolA/CWiFiBalcony
$132/night
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Deacon Stays: The Polo - Walking Distance to Wake Forest University

Deacon Stays: The Polo - Walking Distance to Wake Forest University

4 beds 2 baths
PoolA/CWiFiBalcony
$401/night
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Deacon Stays: The Brookwood - Walk to WFU

Deacon Stays: The Brookwood - Walk to WFU

4 beds 2 baths
PoolA/CWiFiBalcony
$339/night
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Super Cute Condo- DownTown WS/Free Parking/Pets ok

Super Cute Condo- DownTown WS/Free Parking/Pets ok

1 bed 1 bath
PoolA/CWiFiBalcony
$76/night
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Carolina Cheerful and Charming

Carolina Cheerful and Charming

2 beds 1 bath
PoolA/CWiFiBalcony
$131/night
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2BR - Winston’s - Salem - Casa Nova - Getaway

2BR - Winston’s - Salem - Casa Nova - Getaway

2 beds 1 bath
PoolA/CWiFiBalcony
$116/night
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Cheerful cottage w/work space near hospitals

Cheerful cottage w/work space near hospitals

2 beds 1 bath
PoolA/CWiFiBalcony
$210/night
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Luxury Condo/ Roof Top Pool/Amazing Views In The Heart of Downtown WS!!

Luxury Condo/ Roof Top Pool/Amazing Views In The Heart of Downtown WS!!

1 bed 1 bath
PoolA/CWiFiBalcony
$109/night
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Entire condo in historic downtown Winston-salem building

Entire condo in historic downtown Winston-salem building

2 beds 1 bath
PoolA/CWiFiBalcony
$150/night
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Showing 48 of 183 properties

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