Chesapeake, Virginia

Vacation Rentals in Chesapeake, Virginia

Discover 15 vacation rental properties in Chesapeake. From 1 to 4 bedrooms. Average $242/night. 100% have pools.

15 verified listings Book securely on VRBO Prices updated March 2026

15 properties available

Beautifully appointed, spacious ranch style home located in Greenbrier!

Beautifully appointed, spacious ranch style home located in Greenbrier!

3 beds 2 baths
PoolA/CWiFiBalcony
$231/night
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First Class Lvng - 2BR, 2BA, cool & cozy

First Class Lvng - 2BR, 2BA, cool & cozy

2 beds 2 baths
PoolA/CWiFiBalcony
$98/night
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Bright Chesapeake Home Near Shopping & Dining

Bright Chesapeake Home Near Shopping & Dining

2 beds 1 bath
PoolA/CWiFiBalcony
$159/night
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Comfortable Home | Long Stay Discount Available

Comfortable Home | Long Stay Discount Available

3 beds 1 bath
PoolA/CWiFiBalcony
$165/night
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Stylish 3 Bedroom Townhome w/ King Bed & Private Lake Access!

Stylish 3 Bedroom Townhome w/ King Bed & Private Lake Access!

3 beds 2 baths
PoolA/CWiFiBalcony
$263/night
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Great Studio | Pool & Hot Tub. Your Next Vacation

Great Studio | Pool & Hot Tub. Your Next Vacation

1 bath
PoolA/CWiFiBalcony
$240/night
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Convenient to all 7 cities

Convenient to all 7 cities

3 beds 2 baths
PoolA/CWiFiBalcony
$226/night
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Fully renovated and Modernized home in Chesapeake

Fully renovated and Modernized home in Chesapeake

3 beds 2 baths
PoolA/CWiFiBalcony
$257/night
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Ultimate Vacation Home

Ultimate Vacation Home

4 beds 3 baths
PoolA/CWiFiBalcony
$725/night
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King Guest Suite - A TOGAR Vacation Rental

King Guest Suite - A TOGAR Vacation Rental

1 bed 1 bath
PoolA/CWiFiBalcony
$91/night
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1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 bath
PoolA/CWiFiBalcony
$240/night
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Historical section of Chesapeake. Propertie nice and groomed quiet neighborhood.

Historical section of Chesapeake. Propertie nice and groomed quiet neighborhood.

1 bed 1 bath
PoolA/CWiFiBalcony
$251/night
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Country Escape Home in the Woods- Chesapeake VA

Country Escape Home in the Woods- Chesapeake VA

3 beds 1 bath
PoolA/CWiFiBalcony
$159/night
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King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

1 bed 1 bath
PoolA/CWiFiBalcony
$274/night
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Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

1 bed 1 bath
PoolA/CWiFiBalcony
$251/night
View Details → Book on VRBO

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