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Osterville 4+ bedroom Vacation Rentals, Homes & More - 298 Rentals Available.

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298 Vacation rentals

Filters applied: 4+ Bedrooms

Your search has been expanded 19.8 miles to include more rentals

(6)

1 / 23

East Sandwich House - 8.4 miles away

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

$429.00

Very Good (6 reviews)

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from $429.00 / night

(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

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

1 / 12

Oak Bluffs House - 17.4 miles away

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

$328.00

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from $328.00 / night

(5)

1 / 48

Falmouth House - 12.6 miles away

  • 5
  • 15
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly

$1,546.00

Very Good (5 reviews)

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from $1,546.00 / night

1 / 15

East Sandwich House - 8.3 miles away

  • 4
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

$221.00

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from $221.00 / night

(15)

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

$1,071.00

Excellent (15 reviews)

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from $1,071.00 / night

(11)

1 / 18

Sandwich House - 14.6 miles away

  • 4
  • 10
  • min stay varies
  • 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

(1)

1 / 16

West Yarmouth House - 8.1 miles away

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

$950.00

Excellent (1 reviews)

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from $950.00 / night

(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. 46 minutes

$516.00

Excellent (1 reviews)

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from $516.00 / night

(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. 46 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

(2)

1 / 21

Chatham House - 18.6 miles away

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

$372.00

Excellent (2 reviews)

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from $372.00 / night

(2)

1 / 15

Chatham House - 18.6 miles away

  • 4
  • 11
  • 7 nights min
  • Ask about children
  • Air conditioning

$571.00

Excellent (2 reviews)

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from $571.00 / night

1 / 34

Chatham House - 18.8 miles away

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

$643.00

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from $643.00 / night

(4)

1 / 25

Chatham House - 19.6 miles away

  • 4
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$929.00

Excellent (4 reviews)

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from $929.00 / night

(1)

1 / 41

South Chatham House - 18.5 miles away

  • 4
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning

$886.00

Excellent (1 reviews)

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from $886.00 / night

(1)

1 / 24

Chatham House - 18.7 miles away

  • 4
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning

$343.00

Excellent (1 reviews)

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from $343.00 / night

1 / 16

Chatham House - 19.5 miles away

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

$372.00

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from $372.00 / night

(3)

1 / 33

Chatham House - 19 miles away

  • 4
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning

$243.00

Excellent (3 reviews)

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from $243.00 / night

1 / 25

South Chatham House - 18.7 miles away

  • 4
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning

$472.00

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from $472.00 / night

(3)

1 / 30

Chatham House - 19.4 miles away

  • 5
  • 12
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$557.00

Very Good (3 reviews)

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from $557.00 / night

(1)

1 / 38

South Chatham House - 18.8 miles away

  • 4
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning

$1,143.00

Very Good (1 reviews)

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from $1,143.00 / night

1 / 27

Chatham House - 19.6 miles away

  • 6
  • 12
  • 7 nights min
  • Ask about children
  • Air conditioning

$743.00

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from $743.00 / night

1 / 26

South Chatham House - 19 miles away

  • 4
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning

$586.00

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from $586.00 / night

(4)

1 / 23

Chatham House - 18.5 miles away

  • 4
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning

$358.00

Excellent (4 reviews)

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from $358.00 / night

1 / 19

South Chatham House - 19.2 miles away

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

$843.00

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from $843.00 / night

1 / 42

Harwich Port House - 16.7 miles away

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

$901.00

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from $901.00 / night

1 / 28

South Chatham House - 19.1 miles away

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

$800.00

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from $800.00 / night

(1)

1 / 35

South Chatham House - 19.1 miles away

  • 4
  • 12
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$901.00

Very Good (1 reviews)

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from $901.00 / night

(2)

1 / 41

Chatham House - 19.8 miles away

  • 4
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$2,030.00

Excellent (2 reviews)

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from $2,030.00 / night

(1)

1 / 47

Harwich Port House - 16.3 miles away

  • 6
  • 12
  • 7 nights min
  • Ask about children
  • Air conditioning

$1,571.00

Excellent (1 reviews)

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from $1,571.00 / night

(3)

1 / 29

Chatham House - 19.7 miles away

  • 4
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning

$657.00

Excellent (3 reviews)

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from $657.00 / night

1 / 28

South Chatham House - 18.8 miles away

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

$120.00

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from $120.00 / night

1 / 38

South Chatham House - 19.8 miles away

  • 6
  • 10
  • min stay varies
  • Child friendly
  • Pet friendly

$264.00

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from $264.00 / night

1 / 45

Harwich Port House - 16.4 miles away

  • 5
  • 14
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

$525.00

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from $525.00 / night

1 / 39

Brewster House - 17.5 miles away

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

$180.00

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from $180.00 / night

1 / 28

South Chatham House - 19.4 miles away

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

$187.00

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from $187.00 / night

1 / 35

Brewster House - 17 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly
  • Pet friendly

$120.00

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from $120.00 / night

1 / 39

South Chatham House - 18.7 miles away

  • 4
  • 11
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

$156.00

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from $156.00 / night

1 / 47

South Chatham House - 19.1 miles away

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

$134.00

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from $134.00 / night