Osterville Rentals

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267 Houses

271 Westwind Cir

Osterville house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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$220

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

Osterville apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$523

236B Smoke Valley Road 153791

Osterville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$464

Great rentals within 20 miles that match your search

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

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. 8 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

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

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

60 Ploughed Neck Rd.

East Sandwich farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$214

Charming Lambert's Cove Beach House

West Tisbury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$430

Great Place for a Cape Cod Vacation

Barnstable cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$1,145

114 Long Pond Rd

Marstons Mills house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$210

64 Ploughed Neck Rd.

East Sandwich farmhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$200

Martha's Vineyard Rental

Edgartown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$654

36 Salt Marsh Rd.

East Sandwich cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$250

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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Price per night from

$395

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Price per night from

$395

Glendon Beach Cottage #97 100 yds to the beach

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 8 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. 8 minutes

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Price per night from

$201

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$1,963

14 Town Neck

Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$150

Seaside cottage

Falmouth cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$492

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

New Seabury house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$373

244 Phillips Rd

Sagamore Beach cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$170

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

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

131 North Shore Blvd Unit 7

East Sandwich apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$170

99B North Shore Blvd

East Sandwich cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Wonderful” Our stay at north shore Blvd was wonderful. The view was spectactular, the location was great and the house was very nice. There was a small issue of previous damage with the refrigerator drawer, but we called the office right away and reported it to them. Would I rent this location again? Absolutely!!! : )

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Price per night from

$279

99 North Shore Blvd

East Sandwich house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Ideal family cottage” We have stayed in tis cottage for the past few years and it is ideal for our family set up (mother downstairs us and kids upstairs) and is a good value for the price. Although not ocean front it's close enough that it doesn't bother us. We needed to call Sand Dollar because there was no propane tank and they made sure to bring us one the next day. The back entrance was totally overgrown with shrubs and bushes and could not be used-they brought us small pruning shears but they weren't big enough to do the job so hopefully was taken care of for the next renters coming in. The cottage was very clean upon chek in. Overall a very nice vacation and we plan to stay here again next summer.

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Price per night from

$200

Beachland 12

East Sandwich cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Perfect for our Family!” We have stayed in many cottages in East Sandwich and this one is by far our favorite. The view off the back deck is beautiful. It was wonderful having coffee out there in the morning. Also, the breeze you get coming off the marsh is wonderful. The cottage was clean and bright and was perfect for our family of 4! We can't wait to come back and stay again and again and again!

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Price per night from

$150

Beachland K

East Sandwich cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$150

5 Captain Crocker

East Sandwich cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

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Price per night from

$857

14 Benedict Rd

Bourne house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Never Bored in Bourne” This three bedroom home on a tree lined secluded lot offers spectacular views! A large deck facing lush, green tidal pools offer relaxing views. Kitchen/Dining area with loads of counter space allow for lots of family cooking and dining. We had a great time !

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Price per night from

$214

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