Houses Osterville

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898 houses

271 Westwind Cir

Osterville house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$220

OSTERVILLE VILLAGE NEWLY RENOVATED ON 6 ACRES CLOSE TO BEACHES

Osterville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,031

236B Smoke Valley Road 153791

Osterville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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$464

Contemporary Gem with Private Pool!

Osterville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$402

Walk to Joshua Pond Beach & Downtown!

Osterville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$224

Great rentals within 20 miles that match your search

Martha's Vineyard Rental

Edgartown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$654

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Price per night from

$395

Chatham Beach Chic 5⭐ -5 min Walk to Beach! Cape Escape Hear the waves at Night!

South Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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$395

Glendon Beach Cottage #97 100 yds to the beach

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 9 minutes

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Price per night from

$201

Glendon Beach Cottage #93 100 yds to the beach

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Cozy & private by the sea!” My husband & I were looking to stay somewhere quiet & private for our week get-a-way. We were not looking to be entertained, we were looking to relax. This was the right choice for our vacation!. The cottages are nearby each other but separate from each other providing privacy from the neighboring cottages. We stayed in cottage #93 on the end & felt more "secluded" from the driveway/roadway. The beach was a short walk from the cottage - no need to bring the car! There were a number of trips made in the morning to the pretty beach location coffee in hand or a chair, drink & book later in the day. The beach is a rare find during "high season" since there is no fee to use. The cottage itself is small-ish as expected w/2 bedrooms, 1 bathroom, 1 common area for kitchen/living space & a nice size front deck w/a picnic table. Easy enough for simple vacation living. When we arrived, we encountered a couple of issues @ the cottage that were an indication of the previous inhabitants & their negligent & destructive living habits. One call to Jamie and the issues were handled promptly. The Property Management Team came to the property & addressed all concerns immediately! All in all, my husband & I will surely be looking to return to this cottage for another stay - maybe even bring the grandkids next time!

Responds fast! avg. 9 minutes

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Price per night from

$201

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

New Seabury house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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$373

3bd 2 bath steps to private association beach

Dennis Port house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$622

Cliff Cottage By The Pond

Dennis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$148

Excellent location on Martha's Vineyard

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$630

Connors Cottage

West Hyannisport house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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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

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Price per night from

$493

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

Barnstable house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,309

Raised Split Ranch Single House in South Dennis

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$401

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Price per night from

$781

101 Ploughed Neck Rd

East Sandwich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$250

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.

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$456

Beautiful vacation home for rent

Dennis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$524

2 BR Cape Cod Vacation Rental

Mashpee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$1,637

Glendon Beach Cottage #95 100 yds to the beach

Dennis house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Long Weekend” Great location to beach and local places to eat and drink. Easy access to the rest of the Cape. Pet friendly was a plus. The only downer was it stated it slept 6 but only room for 4, this made for some unhappy campers

Responds fast! avg. 9 minutes

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Price per night from

$201

100 Wing Blvd East

East Sandwich house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$320

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$602

Waterfront, Quiet 3 BR Cape-Walk to Beach

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$630

58 Carman Ave

Sandwich house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$240

Charming 3 bdrm cottage - walk to beach

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 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

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Price per night from

$602

Charming 3 Bedroom Colonial In Popponesset

Mashpee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$843

Contemporary 4 Bedroom House One Mile to Beach

New Seabury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$829

Renovated Cape Cod Home -10 Minutes To Beaches & Ctr

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

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Price per night from

$370

Luxurious Captains Mansion - Waterfront, Town, & Beaches - 5 stars

Edgartown house

  • 12 bedrooms
  • 7 bathrooms
  • sleeps 26

“great trip!” Definately would do it again! Loved the house and the area. Marthas Vineyard is a very special place!

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$903

Cape Cod 2 BD cottage (June $1200wk) private beach in W. Hyannisport

West Hyannisport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Our family enjoyed a memorable reunion week in this beach neighb” We spent the week walking to aves, swimming at Squaw Island, golfing, tennis, and dining out at some great restaurants. This beach house has central air, a new gas grill and outdoor shower. All musts for our vacation rental requests. Nice quiet area with great Cape Cod experiences. The house is clean and comfortable. Great master bed. Near boats to the vineyard and Nantucket. We plan on another family reunion vacation at this beach house again this summer.

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Price per night from

$264

GREAT VACATION HOUSE-GREAT LOCATION TO SOUTH BEACH

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$344

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

Dennis Port walk to beach!

Dennis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

“Adorable beachy cottage” Wonderful little cottage. Comfortable slept 4 of us, all the conveniences of home but must bring your own linens/towels/washcloths. Great location, walk to beach, good restaurants. Fireplace provided good heat.

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$229

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