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Search 105,200+ Vacation Rentals

Gloucester 2-bedroom Apartments, Vacation Rentals & More - 52 Rentals Available.

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52 Vacation rentals

Filters applied: 2+ Bedrooms

1 / 31

Gloucester Cottage

  • 7
  • 12
  • 3 nights min
  • Ask about children

$1,549.00

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from $1,549.00 / night

1 / 16

Gloucester Apartment

  • 2
  • 4
  • 7 nights min
  • Ask about children

$340.00

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from $340.00 / night

1 / 20

Gloucester House

  • 3
  • 8
  • 3 nights min
  • Child friendly

$944.00

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from $944.00 / night

1 / 44

Gloucester House

  • 4
  • 10
  • 6 nights min
  • Child friendly

$886.00

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from $886.00 / night

1 / 24

Gloucester House

  • 5
  • 9
  • 3 nights min
  • Child friendly

$1,324.00

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from $1,324.00 / night

1 / 47

Gloucester House

  • 5
  • 10
  • 3 nights min
  • Child friendly
  • Air conditioning

$1,280.00

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from $1,280.00 / night

1 / 33

Gloucester House

  • 4
  • 7
  • 3 nights min
  • Child friendly

$935.00

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from $935.00 / night

1 / 29

Gloucester Cottage

  • 3
  • 7
  • 3 nights min
  • Child friendly

$542.00

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from $542.00 / night

1 / 56

Gloucester House

  • 4
  • 10
  • 3 nights min
  • Child friendly
  • Air conditioning

$1,639.00

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from $1,639.00 / night

1 / 22

Gloucester House

  • 2
  • 6
  • 3 nights min
  • Child friendly
  • Pet friendly

$443.00

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from $443.00 / night

1 / 20

Gloucester House

  • 5
  • 10
  • 6 nights min
  • Child friendly
  • Pet friendly

$708.00

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from $708.00 / night

1 / 36

Gloucester House

  • 2
  • 6
  • 3 nights min
  • Child friendly
  • Air conditioning

$707.00

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from $707.00 / night

1 / 28

Gloucester House

  • 3
  • 8
  • 3 nights min
  • Child friendly
  • Air conditioning

$857.00

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from $857.00 / night

1 / 33

Gloucester House

  • 3
  • 6
  • 6 nights min
  • Ask about children
  • Pet friendly

$736.00

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from $736.00 / night

1 / 53

Gloucester House

  • 6
  • 16
  • 7 nights min
  • Child friendly
  • Air conditioning

$1,362.00

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from $1,362.00 / night

1 / 23

Gloucester House

  • 3
  • 8
  • 6 nights min
  • Child friendly

$560.00

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from $560.00 / night

1 / 14

Gloucester House

  • 3
  • 9
  • 3 nights min
  • Ask about children

$656.00

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from $656.00 / night

1 / 23

Gloucester House

  • 3
  • 7
  • 3 nights min
  • Child friendly
  • Pet friendly

$345.00

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from $345.00 / night

1 / 16

Gloucester Apartment

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Air conditioning

$429.00

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from $429.00 / night

1 / 35

Gloucester House

  • 3
  • 6
  • 3 nights min
  • Child friendly
  • Air conditioning

$698.00

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from $698.00 / night

1 / 40

Gloucester House

  • 3
  • 8
  • 3 nights min
  • Child friendly
  • Air conditioning

$734.00

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from $734.00 / night

1 / 19

Gloucester Condo

  • 2
  • 4
  • 3 nights min
  • Child friendly

$423.00

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from $423.00 / night

1 / 39

Gloucester House

  • 4
  • 10
  • 3 nights min
  • Child friendly
  • Air conditioning

$1,060.00

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from $1,060.00 / night

1 / 44

Gloucester House

  • 6
  • 14
  • 3 nights min
  • Child friendly

$1,286.00

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from $1,286.00 / night

1 / 35

Gloucester House

  • 3
  • 6
  • 3 nights min
  • Child friendly
  • Air conditioning

$600.00

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from $600.00 / night

1 / 17

Gloucester House

  • 4
  • 8
  • 3 nights min
  • Ask about children

$1,285.00

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from $1,285.00 / night

(1)

1 / 27

Gloucester House

  • 2
  • 5
  • 3 nights min
  • Ask about children

$445.00

Excellent (1 reviews)

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from $445.00 / night

1 / 34

Gloucester House

  • 3
  • 6
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$724.00

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from $724.00 / night

(1)

1 / 21

Gloucester House

  • 4
  • 8
  • 3 nights min
  • Ask about children

$1,410.00

Very Good (1 reviews)

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from $1,410.00 / night

1 / 27

Gloucester House

  • 3
  • 6
  • 3 nights min
  • Ask about children

$5,649.00

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from $5,649.00 / night

Your search has been expanded 5.7 miles to include more rentals

(4)

1 / 46

Rockport House - 3.1 miles away

  • 4
  • 14
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

$593.00

Excellent (4 reviews)

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from $593.00 / night

1 / 21

Rockport House - 4 miles away

  • 2
  • 4
  • 3 nights min
  • Ask about children

$511.00

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from $511.00 / night

1 / 23

Manchester-by-the-Sea House - 5.7 miles away

  • 4
  • 8
  • 6 nights min
  • Ask about children

$857.00

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from $857.00 / night

1 / 35

Rockport House - 4.6 miles away

  • 5
  • 9
  • 3 nights min
  • Child friendly
  • Air conditioning

$1,197.00

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from $1,197.00 / night

1 / 43

Rockport House - 4.8 miles away

  • 4
  • 10
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$1,084.00

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from $1,084.00 / night

1 / 64

Rockport House - 3.8 miles away

  • 6
  • 10
  • 3 nights min
  • Child friendly

$2,452.00

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from $2,452.00 / night

1 / 28

Rockport House - 3.9 miles away

  • 4
  • 10
  • 5 nights min
  • Child friendly
  • Air conditioning

$776.00

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from $776.00 / night

1 / 21

Rockport House - 4 miles away

  • 7
  • 14
  • 3 nights min
  • Child friendly

$1,306.00

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from $1,306.00 / night

1 / 29

Rockport House - 4.8 miles away

  • 4
  • 7
  • 3 nights min
  • Child friendly
  • Pet friendly

$767.00

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from $767.00 / night

1 / 39

Rockport House - 2.6 miles away

  • 4
  • 7
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$639.00

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from $639.00 / night