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Chilmark 2-bedroom Vacation Rentals, Homes & More - 643 Rentals Available.

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643 Vacation rentals

Filters applied: 2+ Bedrooms

1 / 18

Chilmark House

  • 4
  • 8
  • 7 nights min
  • Ask about children
  • Air conditioning

$700.00

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from $700.00 / night

1 / 17

Chilmark House

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

$215.00

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from $215.00 / night

1 / 24

Chilmark House

  • 5
  • 12
  • 7 nights min
  • Ask about children

$358.00

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from $358.00 / night

1 / 31

Chilmark House

  • 5
  • 10
  • min stay varies
  • Ask about children
  • Air conditioning

$571.00

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from $571.00 / night

1 / 41

Chilmark House

  • 4
  • 8
  • 14 nights min
  • Ask about children
  • Air conditioning

$1,429.00

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from $1,429.00 / night

1 / 26

Chilmark House

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

$572.00

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from $572.00 / night

1 / 37

Chilmark House

  • 5
  • 9
  • 7 nights min
  • Ask about children
  • Air conditioning

$1,265.00

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from $1,265.00 / night

1 / 10

Chilmark House

  • 4
  • 8
  • 14 nights min
  • Swimming pool
  • Ask about children

$1,179.00

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from $1,179.00 / night

1 / 36

Chilmark House

  • 4
  • 7
  • 7 nights min
  • Ask about children
  • Air conditioning

$929.00

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from $929.00 / night

1 / 33

Chilmark House

  • 4
  • 8
  • 7 nights min
  • Ask about children
  • Air conditioning

$786.00

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from $786.00 / night

1 / 41

Chilmark House

  • 5
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning

$572.00

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from $572.00 / night

1 / 34

Chilmark House

  • 4
  • 8
  • 7 nights min
  • Ask about children
  • Air conditioning

$1,072.00

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from $1,072.00 / night

1 / 11

Chilmark House

  • 4
  • 8
  • 7 nights min
  • Ask about children
  • Air conditioning

$179.00

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from $179.00 / night

1 / 19

Chilmark House

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning

$400.00

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from $400.00 / night

1 / 33

Chilmark House

  • 4
  • 9
  • 7 nights min
  • Ask about children

$1,715.00

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from $1,715.00 / night

1 / 23

Chilmark House

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

$429.00

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from $429.00 / night

1 / 11

Chilmark House

  • 4
  • 8
  • min stay varies
  • Ask about children
  • Air conditioning

$179.00

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from $179.00 / night

1 / 28

Chilmark House

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

$436.00

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from $436.00 / night

(1)

1 / 12

Chilmark House

  • 2
  • 4
  • min stay varies
  • Ask about children

$143.00

Very Good (1 reviews)

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from $143.00 / night

1 / 33

Chilmark House

  • 5
  • 8
  • 7 nights min
  • Ask about children
  • Air conditioning

$1,143.00

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from $1,143.00 / night

1 / 19

Chilmark House

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children

$857.00

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from $857.00 / night

1 / 12

Chilmark House

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

$329.00

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from $329.00 / night

1 / 31

Chilmark House

  • 4
  • 8
  • min stay varies
  • Ask about children
  • Air conditioning

$1,430.00

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from $1,430.00 / night

1 / 11

Chilmark House

  • 5
  • 12
  • 7 nights min
  • Ask about children

$500.00

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from $500.00 / night

1 / 23

Chilmark House

  • 6
  • 10
  • 7 nights min
  • Ask about children

$1,215.00

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from $1,215.00 / night

1 / 13

Chilmark House

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

$258.00

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from $258.00 / night

1 / 16

Chilmark House

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$571.00

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from $571.00 / night

1 / 18

Chilmark House

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning

$286.00

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from $286.00 / night

1 / 21

Chilmark House

  • 4
  • 8
  • min stay varies
  • Ask about children

$314.00

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from $314.00 / night

1 / 15

Chilmark House

  • 4
  • 8
  • min stay varies
  • Ask about children
  • Air conditioning

$1,357.00

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from $1,357.00 / night

1 / 43

Chilmark House

  • 4
  • 8
  • 7 nights min
  • Ask about children
  • Air conditioning

$429.00

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from $429.00 / night

1 / 16

Chilmark House

  • 6
  • 10
  • min stay varies
  • Ask about children

$1,071.00

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from $1,071.00 / night

1 / 29

Chilmark House

  • 4
  • 9
  • 7 nights min
  • Ask about children
  • Air conditioning

$1,429.00

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from $1,429.00 / night

1 / 22

Chilmark House

  • 5
  • 8
  • 14 nights min
  • Ask about children

$715.00

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from $715.00 / night

Your search has been expanded 18.6 miles to include more rentals

(3)

1 / 23

Falmouth House - 18.6 miles away

  • 4
  • 8
  • 1 night min
  • Ask about children
  • Air conditioning
  • Pet friendly
“Welcoming place. My family and I had had a good time staying at this place. Bedrooms were good size, layout of the kitchen and living room were nice along with the interior decoration. They had bikes which we took for a good ride to the beach about 2...”
- Review left on 09/14/2015

$375.00

Very Good (3 reviews)

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from $375.00 / night

1 / 12

Edgartown House - 10.8 miles away

  • 4
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden

$328.00

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from $328.00 / night

(3)

1 / 19

Falmouth House - 15.4 miles away

  • 3
  • 8
  • min stay varies
  • Ask about children
  • Air conditioning

Responds fast! Avg. 3 hours 9 minutes

“A wonderful fall get away! Wonderful location and a fabulous house with great amenities. Would definitely return for future vacations...”
- Review left on 10/27/2016

$458.00

Excellent (3 reviews)

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from $458.00 / night

1 / 15

Falmouth House - 16.2 miles away

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

$400.00

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from $400.00 / night

1 / 21

Oak Bluffs House - 12.7 miles away

  • 3
  • 9
  • min stay varies
  • Ask about children
  • Air conditioning

$786.00

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from $786.00 / night

1 / 31

Vineyard Haven House - 10.6 miles away

  • 6
  • 11
  • 7 nights min
  • Ask about children
  • Air conditioning

$300.00

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from $300.00 / night