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Gloucester Holiday Rentals

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50 rentals in Gloucester.
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Cottage on a Private Island in the York River, holiday rental in Gloucester

Cottage on a Private Island in the York River

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg, holiday rental in Gloucester

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

2 bedrooms
2 bathrooms
Sleeps 4
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A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**, holiday rental in Gloucester

A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Quiet Retreat on North River in Historic Gloucester, Virginia, holiday rental in Gloucester

Charming Quiet Retreat on North River in Historic Gloucester, Virginia

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Waterview & Water Access, Luxurious Retreat, holiday rental in Gloucester

Waterview & Water Access, Luxurious Retreat

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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'Bee Haven' Cottage Retreat Near Colonial Williamsburg, holiday rental in Gloucester

'Bee Haven' Cottage Retreat Near Colonial Williamsburg

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront Home with Pier, 2bds/1ba, holiday rental in Gloucester

Waterfront Home with Pier, 2bds/1ba

2 bedrooms
1 bathroom
Sleeps 4
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Stay on Historic Gloucester Main Street!, holiday rental in Gloucester

Stay on Historic Gloucester Main Street!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Craving small town comfort. Private riverfront for miles, beach, nature for all, holiday rental in Gloucester

Craving small town comfort. Private riverfront for miles, beach, nature for all

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Updated Waterfront Farmhouse on 3 Acres, holiday rental in Gloucester

Updated Waterfront Farmhouse on 3 Acres

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Chesapeake Bay Waterfront Cottage Pool, Pier, Kayaks, Wifi 2 Bd/2 Ba, Mini Golf, holiday rental in Gloucester

Chesapeake Bay Waterfront Cottage Pool, Pier, Kayaks, Wifi 2 Bd/2 Ba, Mini Golf

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Exquisite Riverfront Living! Newly renovated;  convenient to historic sites., holiday rental in Gloucester

Exquisite Riverfront Living! Newly renovated; convenient to historic sites.

5 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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A 1763 Georgian Manor near Williamsburg and Virginia's Historic Triangle, holiday rental in Gloucester

A 1763 Georgian Manor near Williamsburg and Virginia's Historic Triangle

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Chesapeake Bay Waterfront: Kayaks, Fire Pit, Wifi, Bikes, Dog-friendly, holiday rental in Gloucester

Chesapeake Bay Waterfront: Kayaks, Fire Pit, Wifi, Bikes, Dog-friendly

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to The Cottage at Jameslin, holiday rental in Gloucester

Welcome to The Cottage at Jameslin

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Chesapeake Bay Cottage, Private Pool, Pier and Kayaks, holiday rental in Gloucester

Chesapeake Bay Cottage, Private Pool, Pier and Kayaks

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Historic Sea Captain’s Haven on Mobjack Bay, holiday rental in Gloucester

Historic Sea Captain’s Haven on Mobjack Bay

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private Waterfront Retreat, holiday rental in Gloucester

Private Waterfront Retreat

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Historic River Cottage at Glebefield, holiday rental in Gloucester

Historic River Cottage at Glebefield

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Townes at King's Creek Plantation... 4 bedrooms, 2 sunrooms, and more!, holiday rental in Gloucester

The Townes at King's Creek Plantation... 4 bedrooms, 2 sunrooms, and more!

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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King's Creek Plantation: 2-Bedrooms, 2 Baths, Sleep 6, Full Kitchen, holiday rental in Gloucester

King's Creek Plantation: 2-Bedrooms, 2 Baths, Sleep 6, Full Kitchen

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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King's Creek Plantation- 3-Bedroom, Sleeps 10, holiday rental in Gloucester

King's Creek Plantation- 3-Bedroom, Sleeps 10

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spacious 4 bedroom Estate at Kings Creek, holiday rental in Gloucester

Spacious 4 bedroom Estate at Kings Creek

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful 3 bedroom safe and secure, holiday rental in Gloucester

Beautiful 3 bedroom safe and secure

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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The Estates of Kings Creek 3 Bedroom, holiday rental in Gloucester

The Estates of Kings Creek 3 Bedroom

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Charming 3 bedroom in The Cottages at King's Creek Plantation. Click to book!, holiday rental in Gloucester

Charming 3 bedroom in The Cottages at King's Creek Plantation. Click to book!

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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2 bedroom Estate Home safe and secure, holiday rental in Gloucester

2 bedroom Estate Home safe and secure

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Mobjack Bay Cottage Overlooking East River & Mobjack Bay, holiday rental in Gloucester

Mobjack Bay Cottage Overlooking East River & Mobjack Bay

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Cape Cod Located Close to Williamsburg, holiday rental in Gloucester

Charming Cape Cod Located Close to Williamsburg

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Hot fun in the summertime...bring family and friends...plenty of room, holiday rental in Gloucester

Hot fun in the summertime...bring family and friends...plenty of room

4 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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2 Bedroom Townhouse at Kings Creek Plantation Resort, holiday rental in Gloucester

2 Bedroom Townhouse at Kings Creek Plantation Resort

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Restored 1920's Cottage on 1 Acre w/ Fire Pit, holiday rental in Gloucester

NEW! Restored 1920's Cottage on 1 Acre w/ Fire Pit

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Williamsburg Deluxe Cabin, holiday rental in Gloucester

Williamsburg Deluxe Cabin

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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King's Creek Plantation: 1-Bedroom / Sleeps 4 / Full Kitchen, holiday rental in Gloucester

King's Creek Plantation: 1-Bedroom / Sleeps 4 / Full Kitchen

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Williamsburg, VA (Kings Creek) July 2021 rental, holiday rental in Gloucester

Williamsburg, VA (Kings Creek) July 2021 rental

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Kings Creek Plantation Resort - 2 Bedroom Cottage (Week 27), holiday rental in Gloucester

Kings Creek Plantation Resort - 2 Bedroom Cottage (Week 27)

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3 bedroom cottage in beautiful Williamsburg, holiday rental in Gloucester

3 bedroom cottage in beautiful Williamsburg

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful and spacious 1 bedroom in Williamsburg, holiday rental in Gloucester

Beautiful and spacious 1 bedroom in Williamsburg

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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2 Bedroom Estate in beautiful Williamsburg, holiday rental in Gloucester

2 Bedroom Estate in beautiful Williamsburg

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 bedroom within minutes of all Williamsburg has to offer!, holiday rental in Gloucester

2 bedroom within minutes of all Williamsburg has to offer!

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Estates- 2 Bedrooms, holiday rental in Gloucester

The Estates- 2 Bedrooms

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spacious, Comfortable & Relaxing Condo, holiday rental in Gloucester

Spacious, Comfortable & Relaxing Condo

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Mobjack Bay Beach House in Gloucester!, holiday rental in Gloucester

Waterfront Mobjack Bay Beach House in Gloucester!

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Amazing sunsets! Modern amenities on pristine Piankatank, holiday rental in Gloucester

Amazing sunsets! Modern amenities on pristine Piankatank

7 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Waterfront Modern Farmhouse on 22 Private Acres, holiday rental in Gloucester

Waterfront Modern Farmhouse on 22 Private Acres

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Cottages at Kings Creek, holiday rental in Gloucester

The Cottages at Kings Creek

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Cottages at Kings Creek, holiday rental in Gloucester

The Cottages at Kings Creek

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Townes at King Creek, holiday rental in Gloucester

The Townes at King Creek

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Townes at King Creek, holiday rental in Gloucester

The Townes at King Creek

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Kings Creek Cottages, holiday rental in Gloucester

The Kings Creek Cottages

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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