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Osterville 4+ bedroom Vacation Rentals, Homes & More - 315 Rentals Available.

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315 Vacation rentals

Filters applied: 4+ Bedrooms

Your search has been expanded 19.4 miles to include more rentals

(2)

1 / 17

Oak Bluffs Cottage - 14.9 miles away

  • 6
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly

Responds fast! Avg. 20 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

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(3)

1 / 23

Falmouth House - 9.1 miles away

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“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

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(16)

1 / 27

Sandwich House - 6 miles away

  • 6
  • 22
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Our group of 17 recently held a family reunion for one week at this property. The group included young children, teens and adults, and everyone was sad to leave as the week went far too fast. Beautiful property that was extremely well maintained by...”
- Review left on 08/18/2015

$1,285.00

Excellent (16 reviews)

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from $1,285.00 / night

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(1)

1 / 16

West Yarmouth House - 8.1 miles away

  • 4
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Responds fast! Avg. 1 hour 48 minutes

$1,064.00

Excellent (1 reviews)

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from $1,064.00 / night

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1 / 24

Barnstable House - 7.3 miles away

  • 5
  • 8
  • 6 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$573.00

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from $573.00 / night

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(11)

1 / 18

Sandwich House - 14.6 miles away

  • 4
  • 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Ask about children

Responds fast! Avg. 2 hours 2 minutes

“A couple of friends and I decided to rent a house for New Years last minute. After searching for hours, we found, and secured, this house within three days. The owner is cool, very organized, and understanding. Along with that, the house was a great...”
- Review left on 01/19/2016

$367.00

Very Good (11 reviews)

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from $367.00 / night

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(12)

1 / 38

South Yarmouth House - 8.9 miles away

  • 5
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

Responds fast! Avg. 1 hour 5 minutes

“The landlord Alex was very gracious. Everything we needed was provided which was very convenient since we traveled so far. The house was clean and spacious. Centrally located on the cape so we could travel easily in both directions. The beach is only...”
- Review left on 10/20/2016

$572.00

Excellent (12 reviews)

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from $572.00 / night

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1 / 12

Oak Bluffs House - 17.4 miles away

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

$401.00

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from $401.00 / night

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(6)

1 / 23

East Sandwich House - 8.4 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$458.00

Very Good (6 reviews)

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from $458.00 / night

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(1)

1 / 21

Barnstable Villa - 5 miles away

  • 4
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

Responds fast! Avg. 1 hour 5 minutes

$516.00

Excellent (1 reviews)

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from $516.00 / night

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1 / 57

South Chatham House - 19.4 miles away

  • 4
  • 10
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

$248.00

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from $248.00 / night

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1 / 15

East Sandwich House - 8.3 miles away

  • 4
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

$229.00

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from $229.00 / night

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(8)

1 / 21

Sandwich House - 7.6 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$215.00

Excellent (8 reviews)

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from $215.00 / night

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(5)

1 / 19

Sagamore Beach House - 12.7 miles away

  • 7
  • 15
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$358.00

Very Good (5 reviews)

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from $358.00 / night

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(12)

1 / 14

East Sandwich House - 7.2 miles away

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

$229.00

Very Good (12 reviews)

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from $229.00 / night

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(6)

1 / 14

Marstons Mills House - 4.3 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$215.00

Excellent (6 reviews)

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from $215.00 / night

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(7)

1 / 14

Sagamore Beach House - 13.7 miles away

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

$215.00

Excellent (7 reviews)

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from $215.00 / night

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1 / 10

Sandwich House - 11 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$172.00

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from $172.00 / night

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(1)

1 / 19

East Sandwich House - 9.3 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

$429.00

Average (1 reviews)

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from $429.00 / night

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1 / 12

Sandwich House - 11 miles away

  • 5
  • 10
  • 7 nights min
  • Child friendly

$429.00

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from $429.00 / night

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1 / 14

Barnstable House - 6.4 miles away

  • 5
  • 11
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$315.00

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from $315.00 / night

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1 / 13

Sandwich House - 11 miles away

  • 4
  • 9
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$258.00

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from $258.00 / night

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(3)

1 / 14

East Sandwich Cottage - 6.9 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning

$201.00

Very Good (3 reviews)

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from $201.00 / night

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1 / 16

Sandwich House - 11.2 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Pet friendly

$534.00

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from $534.00 / night

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1 / 23

Wareham House - 16.5 miles away

  • 7
  • 20
  • 7 nights min
  • Child friendly
  • Pet friendly

$1,072.00

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from $1,072.00 / night

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1 / 24

Sandwich House - 11.1 miles away

  • 5
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly

$343.00

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from $343.00 / night

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1 / 25

Sandwich House - 11.2 miles away

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$172.00

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from $172.00 / night

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1 / 15

East Sandwich House - 6.1 miles away

  • 4
  • 10
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

$343.00

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from $343.00 / night

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(1)

1 / 26

Barnstable Villa - 5 miles away

  • 5
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly

Responds fast! Avg. 1 hour 5 minutes

$572.00

Excellent (1 reviews)

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from $572.00 / night

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1 / 27

East Sandwich House - 8.6 miles away

  • 4
  • 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly

$486.00

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from $486.00 / night

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1 / 27

East Sandwich House - 7.3 miles away

  • 5
  • 9
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

$258.00

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from $258.00 / night

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(5)

1 / 22

Dennis Port House - 12.8 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning

$129.00

Very Good (5 reviews)

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from $129.00 / night

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1 / 48

West Dennis House - 11.9 miles away

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

$285.00

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from $285.00 / night

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1 / 40

South Yarmouth House - 11.6 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly
  • Air conditioning

$350.00

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from $350.00 / night

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(2)

1 / 30

West Dennis House - 11.9 miles away

  • 4
  • 12
  • 7 nights min
  • Child friendly
  • Air conditioning

$258.00

Very Good (2 reviews)

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from $258.00 / night

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1 / 24

Dennis Port House - 13.1 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning

$358.00

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from $358.00 / night

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(3)

1 / 15

Dennis House - 12.9 miles away

  • 4
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning

$143.00

Very Good (3 reviews)

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from $143.00 / night

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(3)

1 / 20

Dennis Port House - 12.7 miles away

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

$458.00

Average (3 reviews)

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from $458.00 / night

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1 / 37

West Dennis Apartment - 11.9 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning

$315.00

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from $315.00 / night

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(1)

1 / 26

Dennis Port House - 12.3 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning

$229.00

Excellent (1 reviews)

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from $229.00 / night

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