Gloucester, Virginia

Vacation Rentals in Gloucester, Virginia

Discover 19 vacation rental properties in Gloucester. From 1 to 5 bedrooms. Average $235/night. 100% have pools.

19 verified listings Book securely on VRBO Prices updated March 2026

19 properties available

Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

2 beds 2 baths
PoolA/CWiFiBalcony
$226/night
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"Bee Haven" Cottage Retreat Near Colonial Williamsburg

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

2 beds 1 bath
PoolA/CWiFiBalcony
$105/night
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Relaxing Riverfront Cottage w/ Boat Dock!

Relaxing Riverfront Cottage w/ Boat Dock!

2 beds 1 bath
PoolA/CWiFiBalcony
$187/night
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Charming Quiet Retreat on North River in Historic Gloucester, Virginia

Charming Quiet Retreat on North River in Historic Gloucester, Virginia

2 beds
PoolA/CWiFiBalcony
$132/night
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Welcome to this Waterfront Home with Amazing Views

Welcome to this Waterfront Home with Amazing Views

3 beds 2 baths
PoolA/CWiFiBalcony
$151/night
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Historic Cottage on Ware River Estate

Historic Cottage on Ware River Estate

1 bed 1 bath
PoolA/CWiFiBalcony
$151/night
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Riverside farm cottage with pool

Riverside farm cottage with pool

2 beds 1 bath
PoolA/CWiFiBalcony
$201/night
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Bee Humble Cottage w/in 20mins to Public Beaches

Bee Humble Cottage w/in 20mins to Public Beaches

2 beds 1 bath
PoolA/CWiFiBalcony
$99/night
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A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**

A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**

3 beds 2 baths
PoolA/CWiFiBalcony
$216/night
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Right on Main St! Shops, Arts, Dining and More!

Right on Main St! Shops, Arts, Dining and More!

1 bed 1 bath
PoolA/CWiFiBalcony
$131/night
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Beautiful & Peaceful House Overlooking the River. Pets Welcome!

Beautiful & Peaceful House Overlooking the River. Pets Welcome!

3 beds 3 baths
PoolA/CWiFiBalcony
$406/night
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Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!

2 beds 1 bath
PoolA/CWiFiBalcony
$211/night
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Waterview & Water Access, Luxurious Retreat

Waterview & Water Access, Luxurious Retreat

4 beds 2 baths
PoolA/CWiFiBalcony
$257/night
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Squeaky Shores Gloucester, VA Waterfront York River Oasis

Squeaky Shores Gloucester, VA Waterfront York River Oasis

5 beds 4 baths
PoolA/CWiFiBalcony
$498/night
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Gloucester Retreat w/ Backyard Oasis & Pier!

Gloucester Retreat w/ Backyard Oasis & Pier!

4 beds 2 baths
PoolA/CWiFiBalcony
$415/night
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Amazing Waterfront Getawaylong Term Renters are Welcome!

Amazing Waterfront Getawaylong Term Renters are Welcome!

3 beds 2 baths
PoolA/CWiFiBalcony
$385/night
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Renovated Retreat on The York River

Renovated Retreat on The York River

3 beds 2 baths
PoolA/CWiFiBalcony
$352/night
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Cozy Gloucester Getaway w/ Porch & Sunroom!

Cozy Gloucester Getaway w/ Porch & Sunroom!

2 beds 1 bath
PoolA/CWiFiBalcony
$174/night
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Cozy Country setting with comforts of home

Cozy Country setting with comforts of home

3 beds 2 baths
PoolA/CWiFiBalcony
$175/night
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