Osterville Rentals

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271 Westwind Cir

Osterville house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$221

Walk To Joshua Pond & Main St. 2 Bedroom Cottage, Central Cape Location

Osterville apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Children under 5

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Price per night from

$524

OSTERVILLE VILLAGE NEWLY RENOVATED ON 6 ACRES CLOSE TO BEACHES

Osterville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Children under 5

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Price per night from

$1,033

236B Smoke Valley Road 153791

Osterville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Children under 5

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Price per night from

$465

Contemporary Gem with Private Pool!

Osterville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Children under 5

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Price per night from

$403

Walk to Joshua Pond Beach & Downtown!

Osterville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$225

Great rentals within 20 miles that match your search

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Children under 5

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Price per night from

$1,967

14 Town Neck

Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$151

Seaside cottage

Falmouth cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Children under 5

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Price per night from

$493

Popponesset Beach-Mashpee, MA. 4 minute walk to pristine beach.

New Seabury house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Children under 5

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Price per night from

$373

3bd 2 bath steps to private association beach

Dennis Port house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Children under 5

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Price per night from

$623

Excellent location on Martha's Vineyard

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$631

Connors Cottage

West Hyannisport house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Children under 5

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Price per night from

$201

In the Heart of Brewster. Min to Bay Beaches

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Children under 5

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Price per night from

$494

Luxurious & Spacious Waterfront Home on Swimmable Private Beach. Pet OK.

Barnstable house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Children under 5

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Price per night from

$1,312

Match: Children under 5

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Price per night from

$783

Barnstable Village Private Pool

Barnstable house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

“Great place to stay” The home was clean and well maintained. The pool was a huge hit with my niece and the rest of the family. We were in a great location, close to a beach, some shops and restaurants.

Match: Children under 5

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Price per night from

$457

Beautiful vacation home for rent

Dennis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Children under 5

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Price per night from

$525

2 BR Cape Cod Vacation Rental

Mashpee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$1,640

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Children under 5

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Price per night from

$603

Waterfront, Quiet 3 BR Cape-Walk to Beach

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Children under 5

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Price per night from

$631

Charming 3 bdrm cottage - walk to beach

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Children under 5

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Price per night from

$247

3 bedroom 2 bath Fully remodeled home

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$316

Charming 3 Bedroom Colonial In Popponesset

Mashpee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Children under 5

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Price per night from

$845

Contemporary 4 Bedroom House One Mile to Beach

New Seabury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Children under 5

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Price per night from

$831

Renovated Cape Cod Home -10 Minutes To Beaches & Ctr

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Match: Children under 5

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Price per night from

$371

2 min walk to the beach - 30 Union Wharf#3

Dennis Port condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Children under 5

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Price per night from

$287

28-2 Greyneck Road Harwich MA

West Harwich condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Children under 5

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Price per night from

$517

405 Lower County Rd Harwich Port MA

Harwich Port condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Children under 5

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Price per night from

$197

The Berry Quaint Cottage

South Dennis cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Children under 5

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Price per night from

$214

Home Away From Home

South Dennis cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

“South Dennis House” The house we rented was perfect for my family. My girls were happy they each had their own bed! The house had everything we needed. We enjoyed the short travel time to all of the Dennis area beaches. The owners were very friendly and helpful. We had a wonderful time.

Responds fast! avg. 2 hours 39 minutes

Match: Children under 5

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Price per night from

$246

Nice clean house 1/4 mile walk to Sesuit Harbor!

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Children under 5

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Price per night from

$517

Quintessential Cape Cod

West Yarmouth house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Children under 5

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Price per night from

$746

Charming Lambert's Cove Beach House

West Tisbury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Children under 5

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Price per night from

$431

Great Place for a Cape Cod Vacation

Barnstable cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Children under 5

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Price per night from

$1,148

Sweet Cottage in Woods Hole Village Steps to Beach

Woods Hole cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Children under 5

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Price per night from

$431

114 Long Pond Rd

Marstons Mills house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Children under 5

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Price per night from

$211

Martha's Vineyard Rental

Edgartown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Children under 5

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Price per night from

$655

Viewing 38 of 883
rentals in Osterville

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