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Osterville Vacation Rentals & Homes - 875 Rentals Available

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875 Vacation rentals

(2)

1 / 17

Osterville House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$200.00

Excellent (2 reviews)

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from $200.00 / night

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1 / 34

Osterville House

  • 3
  • 8
  • min stay varies
  • Child friendly
  • Air conditioning

$412.00

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from $412.00 / night

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Your search has been expanded 19.4 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

$573.00

Very Good (10 reviews)

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from $573.00 / night

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(10)

1 / 12

Wareham House - 15.8 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“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

$246.00

Very Good (10 reviews)

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from $246.00 / night

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(3)

1 / 21

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. 2 hours 15 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 (3 reviews)

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from $573.00 / 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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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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(8)

1 / 16

Dennis Port Cottage - 13 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“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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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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(6)

1 / 1

South Yarmouth House - 9.2 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“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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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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1 / 8

Sandwich House - 11.2 miles away

  • 3
  • 9
  • 7 nights min
  • Child friendly
  • Pet friendly

$172.00

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from $172.00 / 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 29 minutes

$572.00

Excellent (1 reviews)

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from $572.00 / 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 29 minutes

$516.00

Excellent (1 reviews)

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from $516.00 / 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. 3 hours 37 minutes

$1,064.00

Excellent (1 reviews)

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from $1,064.00 / 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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(3)

1 / 19

Falmouth House - 14.4 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

Responds fast! Avg. 25 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

$916.00

Excellent (3 reviews)

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from $916.00 / night

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(11)

1 / 18

Sandwich House - 14.6 miles away

  • 4
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Ask about children

Responds fast! Avg. 1 hour 56 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

$390.00

Very Good (11 reviews)

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from $390.00 / 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

$230.00

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from $230.00 / night

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(13)

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 29 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 (13 reviews)

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from $572.00 / night

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1 / 10

East Sandwich House - 8.6 miles away

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

$115.00

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from $115.00 / 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 / 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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(4)

1 / 16

Sandwich Cottage - 9.3 miles away

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

$300.00

Average (4 reviews)

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from $300.00 / night

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1 / 30

Forestdale House - 5.2 miles away

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

$286.00

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from $286.00 / night

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(8)

1 / 12

Sandwich House - 11.2 miles away

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

$200.00

Very Good (8 reviews)

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from $200.00 / 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 / 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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(8)

1 / 9

East Sandwich Studio - 8.6 miles away

  • -1
  • 3
  • 7 nights min
  • Child friendly

$122.00

Very Good (8 reviews)

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from $122.00 / 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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(18)

1 / 15

East Sandwich House - 8.9 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$415.00

Very Good (18 reviews)

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from $415.00 / night

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(20)

1 / 10

East Sandwich Cottage - 8 miles away

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

$715.00

Very Good (20 reviews)

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from $715.00 / night

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(4)

1 / 10

Sandwich House - 11.1 miles away

  • 2
  • 5
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$158.00

Excellent (4 reviews)

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from $158.00 / night

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(3)

1 / 14

East Sandwich Cottage - 6.9 miles away

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

$200.00

Very Good (3 reviews)

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from $200.00 / night

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(1)

1 / 10

Falmouth Farmhouse - 9.1 miles away

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

$229.00

Excellent (1 reviews)

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from $229.00 / night

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(1)

1 / 13

East Sandwich Cottage - 8.7 miles away

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

$215.00

Excellent (1 reviews)

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from $215.00 / night

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(1)

1 / 10

Sagamore Beach Cottage - 12.1 miles away

  • 3
  • 6
  • 7 nights min
  • Child friendly

$143.00

Average (1 reviews)

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from $143.00 / 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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