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Essex Vacation Rentals

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50 rentals in Essex.
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Clamshell Landing: Bring your game to its squash & tennis courts!, vacation rental in Essex

Clamshell Landing: Bring your game to its squash & tennis courts!

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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4 Bedroom LUX House/with Pool Next Door, vacation rental in Essex

4 Bedroom LUX House/with Pool Next Door

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quality Accommodations in Quiet Seaside Village, vacation rental in Essex

Quality Accommodations in Quiet Seaside Village

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Oceanfront Home in Estate Setting in Gloucester, vacation rental in Essex

Beautiful Oceanfront Home in Estate Setting in Gloucester

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks-Kayaking, vacation rental in Essex

Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks-Kayaking

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Walk to Good Harbor Beach, pet friendly, family beach home, vacation rental in Essex

Walk to Good Harbor Beach, pet friendly, family beach home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach, vacation rental in Essex

Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Walk to downtown Gloucester & Pavilion Beach!, vacation rental in Essex

Walk to downtown Gloucester & Pavilion Beach!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Romantic SUMMERWIND COTTAGE- Scenic Harbor View, vacation rental in Essex

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW LISTING!~Victorian Getaway Close to Beach, Downtown and Train!, vacation rental in Essex

NEW LISTING!~Victorian Getaway Close to Beach, Downtown and Train!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Welcoming Getway Oasis, vacation rental in Essex

Welcoming Getway Oasis

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA, vacation rental in Essex

Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning SUNSET STUDIO w/Scenic Harbor View, vacation rental in Essex

Stunning SUNSET STUDIO w/Scenic Harbor View

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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La Bohème RETREAT Studio, vacation rental in Essex

La Bohème RETREAT Studio

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Lovely 'Blue Heron Cottage' on Annisquam River!, vacation rental in Essex

Lovely 'Blue Heron Cottage' on Annisquam River!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Coastal, Cute & Cozy|Close to Everything, vacation rental in Essex

Coastal, Cute & Cozy|Close to Everything

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cottage at the Cove: A delightful vacation home close to Plum Cove Beach., vacation rental in Essex

Cottage at the Cove: A delightful vacation home close to Plum Cove Beach.

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Charming apt -2 Bedroom -Close to Beach/Sleeps 6

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
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Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches, vacation rental in Essex

Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ipswich Cottage w/Beautiful Views, 5 Mins to Beach, vacation rental in Essex

Ipswich Cottage w/Beautiful Views, 5 Mins to Beach

4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Annisquam Singing Pines: Private riverfront setting & tidal dock., vacation rental in Essex

Annisquam Singing Pines: Private riverfront setting & tidal dock.

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Sea Fox: Custom-designed home with rights to private Coffins Beach, vacation rental in Essex

Sea Fox: Custom-designed home with rights to private Coffins Beach

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Helena House: European flair, close to Plum Cove Beach., vacation rental in Essex

Helena House: European flair, close to Plum Cove Beach.

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Magnolia Tides: Multi-level waterfront home, vacation rental in Essex

Magnolia Tides: Multi-level waterfront home

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Thurston Point: Waterfront rental with deepwater dock on Annisquam River!, vacation rental in Essex

Thurston Point: Waterfront rental with deepwater dock on Annisquam River!

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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The Cottage, vacation rental in Essex

The Cottage

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Booth Cottage: Walk down a private path to fabled Singing Beach., vacation rental in Essex

Booth Cottage: Walk down a private path to fabled Singing Beach.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom), vacation rental in Essex

Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom)

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sunset Cove: Waterfront home in Goose Cove section of Gloucester, vacation rental in Essex

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perrywinkle: Waterfront on Gloucester’s Rocky Neck., vacation rental in Essex

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Family Tides: Only a half-mile from Good Harbor Beach., vacation rental in Essex

Family Tides: Only a half-mile from Good Harbor Beach.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Waterfront Wonder, vacation rental in Essex

Waterfront Wonder

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf, vacation rental in Essex

Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cedar Ledge Annisquam: Ocean views & traditional New England charm., vacation rental in Essex

Cedar Ledge Annisquam: Ocean views & traditional New England charm.

6 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
More info
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Waterfront Ipswich Escape: 2 Miles to Crane Beach!, vacation rental in Essex

Waterfront Ipswich Escape: 2 Miles to Crane Beach!

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe., vacation rental in Essex

Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Elegant And Expansive Victorian Home -- Weekly Summer, Thanksgiving or Christmas, vacation rental in Essex

Elegant And Expansive Victorian Home -- Weekly Summer, Thanksgiving or Christmas

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Plaisance - Enjoy the best of Gloucester living., vacation rental in Essex

Plaisance - Enjoy the best of Gloucester living.

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Bayview Guest Cottage, vacation rental in Essex

Bayview Guest Cottage

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Squam Light: A newly renovated cottage, nestled in the village of Annisquam., vacation rental in Essex

Squam Light: A newly renovated cottage, nestled in the village of Annisquam.

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Chester Square: Waterfront home in historic Annisquam Village., vacation rental in Essex

Chester Square: Waterfront home in historic Annisquam Village.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Terra Nova Cottage, vacation rental in Essex

Terra Nova Cottage

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck., vacation rental in Essex

Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Mount: Walk to Niles Beach & Rocky Neck from this elegant home., vacation rental in Essex

The Mount: Walk to Niles Beach & Rocky Neck from this elegant home.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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River Watch: Waterfront rental home with views and private dock., vacation rental in Essex

River Watch: Waterfront rental home with views and private dock.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Bray Cottage: A charming cottage close to Wingaersheek Beach., vacation rental in Essex

Bray Cottage: A charming cottage close to Wingaersheek Beach.

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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River's Edge: A charming 2BR riverfront home in Gloucester., vacation rental in Essex

River's Edge: A charming 2BR riverfront home in Gloucester.

3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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