Vacation Rentals By Owner In Gloucester, MA

Ocean front and 3 beaches across,parks, short walk to historic downtown!

Gloucester, Massachusetts, United States

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Exceptional(212)

$141.86

4 Bedroom LUX House/with Pool Next Door

Gloucester, Massachusetts, United States

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Exceptional(12)

$448.9

Walk To Good Harbor, OCEAN VIEWS, Open All Year!

Gloucester, Massachusetts, United States

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Exceptional(50)

$460.76

Newly Renovated Luxury 5BR Home + Office, Walk to Beach & Town

Gloucester, Massachusetts, United States

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Exceptional(9)

$859.56

Mill Pond Cottage: Timeless Gloucester Elegance

Gloucester, Massachusetts, United States

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Exceptional(63)

$316.67

Single Level Home - Steps to Downtown Gloucester & A/C throughout

Gloucester, Massachusetts, United States

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Exceptional(8)

$516.73

Walk to Good Harbor and Long Beach -Vacation Home

Gloucester, Massachusetts, United States

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Exceptional(28)

$688.3

Clean Waterfront Classic Cottage with Private Beach

Gloucester, Massachusetts, United States

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Exceptional(14)

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Historic cottage is steps from the beach on a glorious seaside estate!

Gloucester, Massachusetts, United States

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Exceptional(26)

$611.93

Downtown Dahlias fully remodeled in the heart of Gloucester

Gloucester, Massachusetts, United States

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Exceptional(15)

$1696.72

Stay at Rocky Neck

Gloucester, Massachusetts, United States

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Exceptional(7)

$1051.87

Sea for Miles: Ocean Views in Lanesville

Gloucester, Massachusetts, United States

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Exceptional(12)

$204.29

Beach Gem overlooking Stage Fort Park, Tablet Rock & Cressy's Beach!!!

Gloucester, Massachusetts, United States

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Sleeps

Exceptional(3)

$138.51

Gloucester Large 2-Room Studio, Full Kitchen, Deck

Gloucester, Massachusetts, United States

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Sleeps

$247.97

Harbor View Apartment located in the heart of downtown Gloucester

Gloucester, Massachusetts, United States

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Sleeps

Exceptional(28)

$384.85

Cottage

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

Gloucester, Massachusetts, United States

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Sleeps

$421.11

Cottage

Private Cottage with AC & wifi, Steps to the Beach

Gloucester, Massachusetts, United States

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Sleeps

Exceptional(9)

$1146.05

Stay at Little River

Gloucester, Massachusetts, United States

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Exceptional(3)

$990.78

Beautiful Harbor View Walk to Beach 3b2bKings4beds

Gloucester, Massachusetts, United States

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$1178.63

View 149 Private vacation home

Long Beach House: Large, comfortable home just 285 ft from the white sands!

Gloucester, Massachusetts, United States

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Rent a place that suits your needs

Private vacation home

Most popular vacation rentals in Gloucester

$442.89

1 Mi to Beach! Family Gloucester Gem w/ Yard

Gloucester, Massachusetts, United States

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$473.33

Stay at Niles Beach

Gloucester, Massachusetts, United States

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$459.65

Newly Renovated Luxury 5BR Home + Office, Walk to Beach & Town

Gloucester, Massachusetts, United States

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Sleeps

$454.99

Seaside Village of Lanesville - North Gloucester, MA

Gloucester, Massachusetts, United States

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Sleeps

$452.01

Seaside Escape just steps to Good Harbor beach in Gloucester

Gloucester, Massachusetts, United States

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$443.45

Cape Ann Reset

Gloucester, Massachusetts, United States

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$429.89

2BR/3 BA Harbor Home • Wake up to Ocean Views

Gloucester, Massachusetts, United States

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$399.83

Beautifully renovated home walk to boulevard, town & train

Gloucester, Massachusetts, United States

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$411.56

Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

Gloucester, Massachusetts, United States

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Bath

Sleeps

$483.26