Home Vacation Rentals By Owner In Gloucester, MA

Showing 20 Of 211 Vacation Rentals
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Exceptional(18)

$596.48

/ Nightly
Cottage

Amazing Waterfront/Access 4BDRM in Riggs Point

Gloucester, Massachusetts, United States

Bed 4

Bed

Bath 1

Bath

Sleep 8

Sleeps
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Exceptional(47)

$829.29

/ Nightly
Private Vacation Home

Cape Ann, Annisquam panoramic ocean views from every room.

Gloucester, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 11

Sleeps
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$573.3

/ Nightly
Private Vacation Home

Stay in Central Gloucester

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 11

Sleeps
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$656.8

/ Nightly
Private Vacation Home

Stay at Good Harbor Beach

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(15)

$376.83

/ Nightly
Private Vacation Home

Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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$2242.42

/ Nightly
Private Vacation Home

Edgemoor Estate - 11 Bed/6.5 Bath l Sleeps 32 - Pool, Hot Tub, Walk to Beach

Gloucester, Massachusetts, United States

Bed 11

Bed

Bath 7

Bath

Sleep 32

Sleeps
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$111.12

/ Nightly
Apartment

Walk to MBTA Station! Gloucester Extended Stay

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(118)

$221.54

/ Nightly
Cottage

Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach

Gloucester, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(107)

$394.31

/ Nightly
Private Vacation Home

Walk to Good Harbor Beach. 3BR home, NEW Kitchen

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(2)

$991.9

/ Nightly
Private Vacation Home

Stunning, contemporary 2300 sq ft home with breathtaking views of Ipswich Bay

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$375.57

/ Nightly
Private Vacation Home

House on tidal river, spacious deck, private yard

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(82)

$880.2

/ Nightly
Private Vacation Home

Perfect Good Harbor Beach vacation home for large and/or extended family getaway

Gloucester, Massachusetts, United States

Bed 5

Bed

Bath 6

Bath

Sleep 16

Sleeps
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$1530.82

/ Nightly
Private Vacation Home

Oceanfront Luxury on Gloucester's Back Shore

Gloucester, Massachusetts, United States

Bed 5

Bed

Bath 5

Bath

Sleep 10

Sleeps
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$1089.79

/ Nightly
Private Vacation Home

Stay at Windward Point

Gloucester, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(2)

$252.84

/ Nightly
Private Vacation Home

Seaside Community, Charming Year Round Home, Plum Cove Cottage

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(6)

$357.94

/ Nightly
Private Vacation Home

Stroll to SeaView/Beach; Great Yard

Gloucester, Massachusetts, United States

Bed 4

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(81)

$316.56

/ Nightly
Private Vacation Home

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

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
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$503.95

/ Nightly
Private Vacation Home

Oceanside Estate: Main House & Apt w/beach access

Gloucester, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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$508.24

/ Nightly
Apartment

Guest House on Private Estate with Beach

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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$390.96

/ Nightly
Condo

Stay at the Marina

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Home Rent a place that suits your needs

Private vacation home

Private vacation home

View 149 Private vacation home

Home Most popular vacation rentals in Gloucester

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$442.89

/ Nightly
Private vacation home

1 Mi to Beach! Family Gloucester Gem w/ Yard

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$473.33

/ Nightly
Private vacation home

Stay at Niles Beach

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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$459.65

/ Nightly
Private vacation home

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

Gloucester, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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$454.99

/ Nightly
Apartment

Seaside Village of Lanesville - North Gloucester, MA

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$452.01

/ Nightly
Private vacation home

Seaside Escape just steps to Good Harbor beach in Gloucester

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 0

Bath

Sleep 5

Sleeps
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$443.45

/ Nightly
Private vacation home

Cape Ann Reset

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 0

Bath

Sleep 6

Sleeps
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$429.89

/ Nightly
Private vacation home

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

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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$399.83

/ Nightly
Private vacation home

Beautifully renovated home walk to boulevard, town & train

Gloucester, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 9

Sleeps
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$411.56

/ Nightly
Apartment

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

Gloucester, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$483.26

/ Nightly
Private vacation home

Family Friendly Townhouse 75 steps from Long Beach

Gloucester, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps

Most Popular Cities in Massachusetts