Vacation rentals in Gloucester, VA

Best Vacation rentals and Airbnb offers in Gloucester, VA

Eclectic Apartment- 2-4 friends- Family centered. Safe Neighborhood

Apartment, Gloucester

Eclectic Apartment- 2-4 friends- Family centered. Safe Neighborhood is a apartment in Gloucester, with pool access, parking, and room for a group. This stay gives travelers a comfortable…

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About Eclectic Apartment- 2-4 friends- Family centered. Safe Neighborhood

Eclectic Apartment- 2-4 friends- Family centered. Safe Neighborhood is a apartment in Gloucester, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, parking, onsite parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $971.

From$139/night

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Charming Quiet Retreat on North River in Historic Gloucester, Virginia

Guest House, Gloucester

Charming Quiet Retreat on North River in Historic Gloucester, Virginia is a guest house in Gloucester, with kitchen access and a quieter setting. This stay gives travelers a comfortable…

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About Charming Quiet Retreat on North River in Historic Gloucester, Virginia

Charming Quiet Retreat on North River in Historic Gloucester, Virginia is a guest house in Gloucester, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,006.

From$144/night

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Radiant Gloucester House w/ Private Porch!

Holiday Home, Gloucester

Radiant Gloucester House w/ Private Porch! is a holiday home in Gloucester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch! is a holiday home in Gloucester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,531.

From$148/night

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Relaxing Riverfront Cottage w/ Boat Dock!

Holiday Home, Gloucester

Relaxing Riverfront Cottage w/ Boat Dock! is a holiday home in Gloucester, with parking and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Relaxing Riverfront Cottage w/ Boat Dock!

Relaxing Riverfront Cottage w/ Boat Dock! is a holiday home in Gloucester, with parking and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and non smoking::room.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,722.

From$160/night

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Browse Vacation Rentals with a Pool in Gloucester, VA

Add a pool to the search when you want an easy place to cool off between outings.

Charming 1BR Colonial Condo at Wyndham Kingsgate

Condo, Gloucester

Charming 1BR Colonial Condo at Wyndham Kingsgate is a condo in Gloucester, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Charming 1BR Colonial Condo at Wyndham Kingsgate

Charming 1BR Colonial Condo at Wyndham Kingsgate is a condo in Gloucester, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $793.

From$113/night

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4th OF JULY Special at King's Creek-The Estates1BDR, Min. from Water Country USA

Condo, Gloucester

4th OF JULY Special at King's Creek-The Estates1BDR, Min. from Water Country USA is a condo in Gloucester, with pool access. This stay gives travelers a comfortable base for exploring the…

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About 4th OF JULY Special at King's Creek-The Estates1BDR, Min. from Water Country USA

4th OF JULY Special at King's Creek-The Estates1BDR, Min. from Water Country USA is a condo in Gloucester, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,246.

From$178/night

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Estat - 1BR Unit 1

Holiday Home, Gloucester

Estat - 1BR Unit 1 is a holiday home in Gloucester, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Estat - 1BR Unit 1

Estat - 1BR Unit 1 is a holiday home in Gloucester, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,404.

From$201/night

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Estates - 1BR Unit 2

Holiday Home, Gloucester

Estates - 1BR Unit 2 is a holiday home in Gloucester, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Estates - 1BR Unit 2

Estates - 1BR Unit 2 is a holiday home in Gloucester, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,404.

From$201/night

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Best Gloucester, VA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Williamsburg Executive Rooms near Busch Gardens

Homestay, Gloucester

Williamsburg Executive Rooms near Busch Gardens is a homestay in Gloucester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Williamsburg Executive Rooms near Busch Gardens

Williamsburg Executive Rooms near Busch Gardens is a homestay in Gloucester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $534.

From$65/night

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Charming 2-bedroom house with AC, WiFi in Mathews County Virginia

Holiday Home, Gloucester

Charming 2-bedroom house with AC, WiFi in Mathews County Virginia is a holiday home in Gloucester, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Charming 2-bedroom house with AC, WiFi in Mathews County Virginia

Charming 2-bedroom house with AC, WiFi in Mathews County Virginia is a holiday home in Gloucester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,149.

From$307/night

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Inn at Warner Hall

B & B, Gloucester

Inn at Warner Hall is a b & b in Gloucester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Inn at Warner Hall

Inn at Warner Hall is a b & b in Gloucester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free breakfast, free wifi, parking, paid parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,244.

From$293/night

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Warner Hall

B & B, Gloucester

Warner Hall is a b & b in Gloucester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About Warner Hall

Warner Hall is a b & b in Gloucester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free breakfast, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,285.

From$293/night

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Best Pet-Friendly Vacation Rentals in Gloucester, VA

Bring your pet along with stays that welcome four-legged travelers.

Rooftop Chesapeake Bay Views! Waterfront Retreat

Apartment, Gloucester

Rooftop Chesapeake Bay Views! Waterfront Retreat is a apartment in Gloucester, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for…

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About Rooftop Chesapeake Bay Views! Waterfront Retreat

Rooftop Chesapeake Bay Views! Waterfront Retreat is a apartment in Gloucester, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,531.

From$176/night

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Rooftop Chesapeake Bay Views! Waterfront Retreat

Apartment, Gloucester

Rooftop Chesapeake Bay Views! Waterfront Retreat is a apartment in Gloucester, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for…

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About Rooftop Chesapeake Bay Views! Waterfront Retreat

Rooftop Chesapeake Bay Views! Waterfront Retreat is a apartment in Gloucester, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,258.

From$180/night

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Charming 3-bedroom house / Private Pool + Game Room

Holiday Home, Gloucester

Charming 3-bedroom house / Private Pool + Game Room is a holiday home in Gloucester, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base…

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About Charming 3-bedroom house / Private Pool + Game Room

Charming 3-bedroom house / Private Pool + Game Room is a holiday home in Gloucester, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,570.

From$224/night

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Waterfront Hartfield Vacation Rental w/ Dock!

Holiday Home, Gloucester

Waterfront Hartfield Vacation Rental w/ Dock! is a holiday home in Gloucester, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Waterfront Hartfield Vacation Rental w/ Dock!

Waterfront Hartfield Vacation Rental w/ Dock! is a holiday home in Gloucester, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,607.

From$269/night

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Best Gloucester, VA vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Charming 1BR Colonial Condo at Wyndham Kingsgate

Condo, Gloucester

Charming 1BR Colonial Condo at Wyndham Kingsgate is a condo in Gloucester, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Charming 1BR Colonial Condo at Wyndham Kingsgate

Charming 1BR Colonial Condo at Wyndham Kingsgate is a condo in Gloucester, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $800.

From$114/night

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Charming 1BR Colonial Condo at Wyndham Kingsgate

Condo, Gloucester

Charming 1BR Colonial Condo at Wyndham Kingsgate is a condo in Gloucester, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Charming 1BR Colonial Condo at Wyndham Kingsgate

Charming 1BR Colonial Condo at Wyndham Kingsgate is a condo in Gloucester, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $800.

From$114/night

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Charming 1BR Colonial Condo at Wyndham Kingsgate

Condo, Gloucester

Charming 1BR Colonial Condo at Wyndham Kingsgate is a condo in Gloucester, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

Read more

About Charming 1BR Colonial Condo at Wyndham Kingsgate

Charming 1BR Colonial Condo at Wyndham Kingsgate is a condo in Gloucester, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $800.

From$114/night

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1 Bedroom Estates Suite Village in King's Creek weekly booking 8 days/7 nights.

Holiday Home, Gloucester

1 Bedroom Estates Suite Village in King's Creek weekly booking 8 days/7 nights. is a holiday home in Gloucester, with kitchen access and room for a group. This stay gives travelers a…

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About 1 Bedroom Estates Suite Village in King's Creek weekly booking 8 days/7 nights.

1 Bedroom Estates Suite Village in King's Creek weekly booking 8 days/7 nights. is a holiday home in Gloucester, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,350.

From$193/night

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Our Favorite Family-Friendly Vacation Rentals in Gloucester, VA

Plan a trip with stays that give families more room to spread out.

1 Bedroom Cottage Suite Village in King's Creek weekly booking 8days/7nights.

Cottage, Gloucester

1 Bedroom Cottage Suite Village in King's Creek weekly booking 8days/7nights. is a cottage in Gloucester, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About 1 Bedroom Cottage Suite Village in King's Creek weekly booking 8days/7nights.

1 Bedroom Cottage Suite Village in King's Creek weekly booking 8days/7nights. is a cottage in Gloucester, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,292.

From$185/night

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Relaxing Riverfront Cottage w/ Boat Dock!

Cottage, Gloucester

Relaxing Riverfront Cottage w/ Boat Dock! is a cottage in Gloucester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Relaxing Riverfront Cottage w/ Boat Dock!

Relaxing Riverfront Cottage w/ Boat Dock! is a cottage in Gloucester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,780.

From$194/night

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Relaxing Riverfront Cottage w/ Boat Dock!

Cottage, Gloucester

Relaxing Riverfront Cottage w/ Boat Dock! is a cottage in Gloucester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Relaxing Riverfront Cottage w/ Boat Dock!

Relaxing Riverfront Cottage w/ Boat Dock! is a cottage in Gloucester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,600.

From$229/night

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Waterfront with Private Pier and Tranquil Water views!

Cottage, Gloucester

Waterfront with Private Pier and Tranquil Water views! is a cottage in Gloucester, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Waterfront with Private Pier and Tranquil Water views!

Waterfront with Private Pier and Tranquil Water views! is a cottage in Gloucester, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,737.

From$248/night

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