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Osterville Vacation Rentals & Homes - 979 Rentals Available

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979 Vacation rentals

1 / 29

Osterville House

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

$172.00

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from $172.00 / night

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(2)

1 / 17

Osterville House

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

$140.00

Excellent (2 reviews)

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from $140.00 / night

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1 / 18

Osterville House

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

$300.00

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from $300.00 / night

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Your search has been expanded 19.6 miles to include more rentals

(10)

1 / 38

Onset House - 16 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
“we just wanted a relaxing vacation for my 85 year old mother. we couldnt have picked a more perfect home.. so beautiful sitting on the deck right on the water!! the house was very clean & so comfortable..would love to come back next year...”
- Review left on 08/01/2016

$360.00

Very Good (10 reviews)

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from $360.00 / 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

$220.00

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from $220.00 / 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

$328.00

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from $328.00 / night

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(6)

1 / 1

South Yarmouth House - 9.2 miles away

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

Responds fast! Avg. 3 hours 7 minutes

“This house was spacious, clean and affordable. It is an easy walk to the beach and is close to many attractions on the Cape. We plan on renting next year...”
- Review left on 08/08/2016

$221.00

Excellent (6 reviews)

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from $221.00 / night

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(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. 17 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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1 / 24

Barnstable House - 7.3 miles away

  • 5
  • 8
  • 14 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$409.00

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from $409.00 / night

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(8)

1 / 16

Dennis Port Cottage - 13 miles away

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

Responds fast! Avg. 3 hours 25 minutes

“We rented this cottage without seeing it. It was really nice to be so pleasantly surprised, everything was perfect. Great location, close to beaches and all Dennis activities and restaurants. It was immaculate, the central air conditioning was...”
- Review left on 08/14/2016

$221.00

Excellent (8 reviews)

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from $221.00 / night

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(7)

1 / 13

Chatham Cottage - 19.6 miles away

  • 2
  • 5
  • 7 nights min
  • Nearest beach 0.85 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 0 minutes

“The cottage was located only about 1/2 mile from Cockle Cove Beach. It sits in a small private, loop road, surrounded by trees and beyond the trees is the beginnings of a salt marsh. The kitchen is very functional and there's a nice sized dining...”
- Review left on 09/30/2016

$131.00

Very Good (7 reviews)

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from $131.00 / night

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(8)

1 / 12

Wareham House - 15.8 miles away

  • 3
  • 6
  • min stay varies
  • Ask about children
  • Air conditioning
  • Private garden
“I and my family of 7 have enjoyed staying here for our second, precious, annual summer getaway and we're looking forward to our third. It's just perfect. Clean, comfortable, air conditioned. Morning coffee watching the sun rise from the spacious deck...”
- Review left on 09/25/2015

$197.00

Very Good (8 reviews)

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from $197.00 / night

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(1)

1 / 16

Falmouth House - 8.8 miles away

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$430.00

Excellent (1 reviews)

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from $430.00 / night

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(5)

1 / 49

Falmouth House - 12.6 miles away

  • 5
  • 15
  • 4 nights min
  • Nearest beach 0.5 mi
  • Child friendly
  • Air conditioning

$1,546.00

Very Good (5 reviews)

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from $1,546.00 / night

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(3)

1 / 19

Falmouth House - 14.4 miles away

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

Responds fast! Avg. 2 hours 34 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

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(11)

1 / 25

Sandwich House - 6 miles away

  • 6
  • 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“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 (11 reviews)

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from $1,071.00 / 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

$870.00

Excellent (1 reviews)

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from $870.00 / night

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1 / 41

West Dennis House - 10.9 miles away

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

$329.00

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from $329.00 / night

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(12)

1 / 18

Mashpee House - 6.6 miles away

  • 3
  • 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“This is my 7th visit to the Cape and by far the nicest places we have stayed, absolutely perfect in every way. The house is large, spacious and homely, situated on the edge of St Johns Cove which lends itself to the most spectacular sunrises and...”
- Review left on 11/03/2016

$361.00

Excellent (12 reviews)

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from $361.00 / night

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(2)

1 / 30

West Dennis House - 11.9 miles away

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

$215.00

Very Good (2 reviews)

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from $215.00 / night

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1 / 19

West Dennis House - 12.1 miles away

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

$143.00

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from $143.00 / night

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1 / 18

Dennis Port House - 13.6 miles away

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

$72.00

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from $72.00 / night

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1 / 26

Dennis Port House - 13 miles away

  • 3
  • 6
  • 7 nights min
  • Child friendly

$122.00

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from $122.00 / night

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1 / 27

Dennis House - 12.9 miles away

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

$236.00

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from $236.00 / night

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1 / 23

West Dennis Apartment - 11.8 miles away

  • 6
  • 12
  • 7 nights min
  • Child friendly
  • Air conditioning

$251.00

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from $251.00 / night

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1 / 12

West Dennis House - 10.8 miles away

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

$172.00

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from $172.00 / night

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1 / 23

Dennis Port House - 12.9 miles away

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

$129.00

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from $129.00 / night

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(5)

1 / 12

Dennis Port House - 12.7 miles away

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$97.00

Excellent (5 reviews)

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from $97.00 / night

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(2)

1 / 22

Dennis Port House - 12.9 miles away

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

$143.00

Average (2 reviews)

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from $143.00 / night

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(4)

1 / 14

South Dennis House - 12.7 miles away

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

$115.00

Very Good (4 reviews)

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from $115.00 / night

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1 / 25

East Dennis House - 13.6 miles away

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

$143.00

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from $143.00 / night

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1 / 13

Dennis Port House - 12.6 miles away

  • 1
  • 4
  • 7 nights min
  • Child friendly
  • Air conditioning

$115.00

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from $115.00 / night

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(2)

1 / 16

Dennis Port House - 12.6 miles away

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

$93.00

Average (2 reviews)

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from $93.00 / night

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(4)

1 / 13

Dennis Port House - 13.2 miles away

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

$229.00

Very Good (4 reviews)

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from $229.00 / night

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1 / 19

West Dennis House - 11.9 miles away

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

$200.00

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from $200.00 / night

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1 / 18

Dennis Port House - 12.5 miles away

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

$122.00

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from $122.00 / night

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(1)

1 / 12

Dennis Port House - 13.2 miles away

  • 2
  • 4
  • 7 nights min
  • Child friendly

$100.00

Average (1 reviews)

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from $100.00 / night

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(1)

1 / 14

West Dennis House - 11.9 miles away

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

$115.00

Very Good (1 reviews)

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from $115.00 / night

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1 / 22

Dennis House - 12.3 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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1 / 19

Dennis Port House - 13.3 miles away

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

$164.00

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from $164.00 / night

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