Home Vacation Rentals By Owner In Gloucester, MA

Showing 80 Of 211 Vacation Rentals
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Exceptional(1)

$1263.07

/ Nightly
Private Vacation Home

Gull's Nest - Ocean Views from the Living Room

Gloucester, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(55)

$175.93

/ Nightly
Apartment

Walk to the ocean, very private. Secluded, woodsy location.

Gloucester, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(26)

$586.23

/ Nightly
Private Vacation Home

Short Walk to Cape Ann's Best Beaches!

Gloucester, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(15)

$351.3

/ Nightly
Apartment

Blue Magnolia - A quiet apartment in a quaint Gloucester MA village

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(6)

$673.75

/ Nightly
Private Vacation Home

The Haabah Beach Retreat—4 Minute Walk to Beach

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(5)

$1232.05

/ Nightly
Cottage

1886 Captains Carriage House Secluded Luxury Eastern Point Gloucester MA

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(3)

Select Dates for Price
Private Vacation Home

Stay at Good Harbor Beach

Gloucester, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 13

Sleeps
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Exceptional(11)

$247.42

/ Nightly
Cottage

Beautiful cottage on lovingly landscaped property just 5 minute walk to ocean!

Gloucester, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(2)

$981.78

/ Nightly
Private Vacation Home

Squam Light: Nestled in the heart of Annisquam

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 9

Sleeps
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$502.15

/ Nightly
Cottage

cottage close to long beach and good harbor

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(13)

$418.99

/ 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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Exceptional(5)

$931.09

/ Nightly
Private Vacation Home

Wingaerchic: Woodsy retreat right by the beach

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(52)

$341.16

/ Nightly
Private Vacation Home

Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(60)

$580.89

/ Nightly
Cottage

Dog-Friendly, Waterfront Home with Washer and dryer & Two Decks

Gloucester, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(3)

$305.51

/ Nightly
Private Vacation Home

Centrally located charmer with expansive patio, board games, & central AC

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(13)

$383.92

/ Nightly
Private Vacation Home

Peaceful centrally located home: w/ yard & walking distance to town

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(42)

$426.07

/ Nightly
Private Vacation Home

Coastal retreat steps to the beach with smart TVs, desk, grill, children's items

Gloucester, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$2985.62

/ Nightly
Private Vacation Home

Private beachfront escape on Coffins Beach w/ amazing views & private beach

Gloucester, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(27)

$364.89

/ Nightly
Apartment

Centrally located open concept apartment with parking, central AC, & W/D

Gloucester, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(2)

$394.8

/ 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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View 149 Private vacation home

Home Most popular vacation rentals in Gloucester

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Exceptional(2)

$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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Exceptional(2)

$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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Exceptional(2)

$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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Exceptional(2)

$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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Exceptional(2)

$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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Exceptional(2)

$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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Exceptional(2)

$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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Exceptional(2)

$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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Exceptional(2)

$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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Exceptional(2)

$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