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Osterville 4+ bedroom Vacation Rentals, Homes & More - 645 Rentals Available.

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645 Vacation rentals

Filters applied: 4+ Bedrooms

1 / 31

Osterville House

  • 8
  • 20
  • 1 night min
  • Ask about children
  • Pet friendly

$1,875.00

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from $1,875.00 / night

1 / 24

Osterville House

  • 5
  • 12
  • 1 night min
  • Ask about children
  • Ask about pets

$285.00

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from $285.00 / night

1 / 28

Osterville House

  • 6
  • 12
  • 1 night min
  • Swimming pool
  • Ask about children
  • Pet friendly

$3,571.00

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from $3,571.00 / night

1 / 23

Osterville House

  • 5
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$2,857.00

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from $2,857.00 / night

(1)

1 / 38

Osterville House

  • 4
  • 8
  • 1 night min
  • Ask about children
  • Ask about pets

$357.00

Excellent (1 reviews)

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from $357.00 / night

1 / 43

Osterville House

  • 6
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,571.00

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from $2,571.00 / night

1 / 37

Osterville House

  • 5
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,857.00

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from $2,857.00 / night

1 / 29

Osterville House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,072.00

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from $1,072.00 / night

(2)

1 / 20

Osterville House

  • 4
  • 10
  • 1 night min
  • Ask about children
  • Pet friendly

$571.00

Excellent (2 reviews)

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from $571.00 / night

(2)

1 / 19

Osterville House

  • 4
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$271.00

Excellent (2 reviews)

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from $271.00 / night

(1)

1 / 44

Osterville House

  • 5
  • 8
  • 1 night min
  • Ask about children
  • Ask about pets

$1,714.00

Excellent (1 reviews)

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from $1,714.00 / night

(3)

1 / 64

Osterville House

  • 10
  • 22
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,857.00

Excellent (3 reviews)

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from $2,857.00 / night

(1)

1 / 51

Osterville House

  • 9
  • 1
  • 1 night min
  • Ask about children
  • Pet friendly

$4,285.00

Excellent (1 reviews)

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from $4,285.00 / night

(1)

1 / 49

Osterville House

  • 11
  • 20
  • 1 night min
  • Ask about children
  • Pet friendly

$1,928.00

Very Good (1 reviews)

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from $1,928.00 / night

1 / 30

Osterville House

  • 4
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$429.00

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from $429.00 / night

1 / 32

Osterville House

  • 4
  • 8
  • 1 night min
  • Ask about children
  • Ask about pets

$714.00

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from $714.00 / night

(1)

1 / 45

Osterville House

  • 4
  • 9
  • 1 night min
  • Ask about children
  • Ask about pets

$1,028.00

Excellent (1 reviews)

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from $1,028.00 / night

1 / 18

Osterville House

  • 5
  • 12
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,142.00

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from $1,142.00 / night

1 / 43

Osterville House

  • 6
  • 12
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,142.00

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from $2,142.00 / night

1 / 44

Osterville House

  • 6
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,857.00

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from $2,857.00 / night

(1)

1 / 21

Osterville House

  • 5
  • 10
  • 1 night min
  • Ask about children
  • Ask about pets

$714.00

Excellent (1 reviews)

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from $714.00 / night

1 / 50

Osterville House

  • 5
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,571.00

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from $1,571.00 / night

(1)

1 / 33

Osterville House

  • 4
  • 8
  • 1 night min
  • Ask about children
  • Ask about pets

$500.00

Excellent (1 reviews)

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from $500.00 / night

1 / 55

Osterville House

  • 9
  • 12
  • 1 night min
  • Ask about children
  • Pet friendly

$1,857.00

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from $1,857.00 / night

1 / 54

Osterville House

  • 6
  • 14
  • 1 night min
  • Swimming pool
  • Ask about children
  • Pet friendly

$3,571.00

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from $3,571.00 / night

(1)

1 / 43

Osterville House

  • 7
  • 14
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,286.00

Excellent (1 reviews)

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from $1,286.00 / night

1 / 50

Osterville House

  • 5
  • 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,214.00

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from $2,214.00 / night

1 / 29

Osterville House

  • 4
  • 7
  • 1 night min
  • Ask about children
  • Ask about pets

$500.00

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from $500.00 / night

Your search has been expanded 19.6 miles to include more rentals

1 / 23

Vineyard Haven House - 15.8 miles away

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

$429.00

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from $429.00 / night

1 / 12

Oak Bluffs House - 17.4 miles away

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

$295.00

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from $295.00 / night

(2)

1 / 17

Oak Bluffs Cottage - 14.9 miles away

  • 6
  • 10
  • min stay varies
  • Nearest beach 0.2 mi
  • Child friendly
  • Car not necessary

Responds fast! Avg. 47 minutes

“Great house and location! If you are looking for something with space, as well as the ability to walk to the bars and restaurants in Oak Bluffs, this is the house for you! Great location and great porch for those nights when you want to hang in....”
- Review left on 07/20/2014

$573.00

Excellent (2 reviews)

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from $573.00 / night

(5)

1 / 34

Yarmouth House - 9.6 miles away

  • 5
  • 10
  • min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 38 minutes

“My family rented the house for one week. It was exactly as described. We had plenty of room for ourselves and our guests. The beds were comfortable and they provide the linens. With 3 bathrooms and an outdoor shower no one was ever waiting. This is...”
- Review left on 09/08/2016

$343.00

Very Good (5 reviews)

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from $343.00 / night

(5)

1 / 54

Barnstable House - 6.4 miles away

  • 5
  • 10
  • 7 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Ask about children

$572.00

Excellent (5 reviews)

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from $572.00 / night

(4)

1 / 25

Plymouth House - 16.5 miles away

  • 4
  • 8
  • 5 nights min
  • Nearest beach 6 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 33 minutes

$344.00

Excellent (4 reviews)

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from $344.00 / night

(19)

1 / 31

Falmouth House - 13.1 miles away

  • 5
  • 10
  • min stay varies
  • Ask about children
  • Private garden
“The Old Stone Barn is a charming home, with a fantastic view down to Buzzard's Bay and plenty of space for a large family or group of friends to gather. The home is also well appointed and conveniently located with easy access to the bike path, the...”
- Review left on 08/30/2016

$250.00

Excellent (19 reviews)

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from $250.00 / night

(1)

1 / 26

Barnstable Villa - 5 miles away

  • 5
  • 10
  • min stay varies
  • Nearest beach 0.2 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 38 minutes

$366.00

Excellent (1 reviews)

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from $366.00 / night

1 / 15

Brewster House - 19.6 miles away

  • 5
  • 12
  • 7 nights min
  • Child friendly
  • Air conditioning

$285.00

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from $285.00 / night

(1)

1 / 17

Falmouth House - 12.2 miles away

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

$543.00

Excellent (1 reviews)

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from $543.00 / night

(3)

1 / 23

Falmouth House - 9.1 miles away

  • 4
  • 8
  • 1 night min
  • Ask about children
  • Air conditioning
  • Pet friendly

Responds fast! Avg. 3 hours 6 minutes

“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

$430.00

Very Good (3 reviews)

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from $430.00 / night

(1)

1 / 21

Barnstable Villa - 5 miles away

  • 4
  • 10
  • min stay varies
  • Nearest beach 0.1 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 38 minutes

$343.00

Excellent (1 reviews)

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from $343.00 / night