Osterville Rentals

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669 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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$464

Contemporary Gem with Private Pool!

Osterville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$402

Walk to Joshua Pond Beach & Downtown!

Osterville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$224

Great rentals within 20 miles that match your search

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$395

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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$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

In the Heart of Brewster. Min to Bay Beaches

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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$493

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$781

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

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$602

High End-suite style cottage 5 min bike ride to amazing Craigville Beach.

Centerville cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$344

3 bedroom 2 bath Fully remodeled home

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$315

Charming 3 Bedroom Colonial In Popponesset

Mashpee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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$843

Contemporary 4 Bedroom House One Mile to Beach

New Seabury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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$829

103 North Shore Blvd unit 3

East Sandwich apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$157

34 Salt Marsh Rd

East Sandwich cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

“Perfect Cape Vacation Experience” This was a waterfront property with marsh across the street, on a quiet private beach. The photos are very true to life, and the house was well equipped with pots and pans, cups, even bug spray. There were great views from the house, and it was truly relaxing to see and hear the waves from anywhere on the property. The rental company was excellent - key was ready for us, linens and chairs waiting on the porch when we arrived. Very close to 6a - grocery, restaurants, ice cream :) - but also remote location without any public traffic in the neighborhood. I could not have asked for a better house or location for our Cape vacation - we will be returning next year!

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$370

Beachland I

East Sandwich cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Clean, good location, family friendly” We loved being so close to bay. Very family friendly. Very clean. Would come here again. Our only complaint is the "trundle bed" was not a true trundle with another twin bed under. It was drawers. Thank goodness we brought an extra air mattress!!

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$170

Oceanside 1

East Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Peaceful” Beauifully decorated very clean house. Great location. Tiny but all we needed! Very quiet area.

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$132

89-2 Salt Marsh Rd

East Sandwich cottage

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“A piece of heaven!” This was our second year renting this house. It is airy, comfortable,and it's proximity to the beach is ideal. We really enjoyed the upstairs deck and the living room upstairs. The kitchen is well equipped. We grill a lot and had to fill the propane tank on the grill for the second time this year. That might be something to check before renters arrive. Location is close to shopping, laundry facilities, and restaurants. We didn't leave much because we loved it there. We enjoyed playing games on the beach, and taking daily runs, walks on the road and beach. Plenty of games, puzzles, etc. in the house which our kids took advantage of. We rented kayaks from Ride away Kayaks and they were great- delivered them and picked them up. We kayaked every day. Overall, one of our best vacations. Sand Dollar Realty was great to work with. Very professional, organized, and made arrival and departure very smooth.

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$210

Dune Tootin Unit 1

East Sandwich cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Life is good!!” We had three generations traveling with us. These cottages were perfect. We had our privacy and we could be together when we wanted. They were well equipped. Location was wonderful. Time just went too fast!!!

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$214

Heated Pool, AC, WiFi, Sleeps 18, 2 mi to beach!

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

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$6,870

Vineyard Haven Guest House - Sleeps 4, A/C, Walk to Town

Vineyard Haven house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“great stay in Vineyard Haven” We enjoyed staying in David's guest house. It was clean, well situated (a short walk from downtown Vineyard Haven), and made for a relaxing few days on the Vineyard. David was easy to reach and very responsive to any of our needs. I would highly recommend you stay at the guesthouse.

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$264

Waterfront home - Spectacular Sunsets

Bourne house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

“Peace & Tranquility” I have stayed here 4+ times, and I come home relaxed and rejuvenated. It's centrally located in the middle of the western cape, the sunsets are perfect, we usually have meals out on the expansive deck, we bring our kayaks, watch the shipping entering the canal, walk/run/bike the canal path(both sides), cook or grill fresh seafood from local stores, enjoy the wine tastings at the Belfry, jump over to the vineyard for the day, and did I mention the sunsets? The home is roomy, light and airy, plenty of parking, just perfect for us.

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Price per night from

$630

“Great time!!” This wonderful home was great for our Cape vacation! The home is beautiful and the owner's pride and love for their home shows throughout the property. The owners were excellent to work with, very professional and very responsive to inquiries. The house is beautifully decorated and extremely well stocked with everything we needed to make our vacation perfect. We appreciated all the amenities - inside and out, the huge rear deck was one of our favorite places to relax and enjoy the quiet area and the beautiful landscaping, we could even hear the waves at night. The location was very convenient to restaurants, shops and beaches and is centrally located to exploring anywhere on the Cape. We are looking forward to calling this our "home away from home" again!!!

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$395

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$733

Beautiful Home - Great Price, Wi Fi, Flat Screen

Yarmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$201

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 34 minutes

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Price per night from

$229

Waterfront Resort in Falmouth - 5/31/24 - 6/7/24

Falmouth apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$172

Katama House "CLOSE TO THE BEACH"

Acushnet house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$311

Great Family Home, Close to South Beach, And Town

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

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