Osterville Rentals

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289 Houses

271 Westwind Cir

Osterville house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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$220

Great rentals within 20 miles that match your search

Excellent location on Martha's Vineyard

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$630

In the Heart of Brewster. Min to Bay Beaches

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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$493

Raised Split Ranch Single House in South Dennis

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$401

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$781

Beautiful vacation home for rent

Dennis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$524

2 BR Cape Cod Vacation Rental

Mashpee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$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

Charming 3 Bedroom Colonial In Popponesset

Mashpee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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$843

Renovated Cape Cod Home -10 Minutes To Beaches & Ctr

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

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$370

5 Captain Crocker

East Sandwich cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

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$857

173C North Shore Blvd

East Sandwich cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Great cottage! Clean, updated, cair, laundry, outside shower. Hi” This is a wonderful a very comfortable cottage. Great for a family of up to 5. Very modern, hardwood floors, central air, laundry, storage space for bikes, fishing equipment, etc. Quick walk to a very quiet beach. The low tides are awesome! Surrounding cottages are very nice. The town of East Sandwich is very quiet. Great restaurants, ice cream, antiques, etc.

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$210

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

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

41 Cranberry Trail

East Sandwich house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“most relaxing getaway ever.” My friends and I needed a break from the city this spring and this house served us incredibly well. It's spacious and, even with a house full of people, offers an incredible amount of privacy. The large kitchen is perfect for cooking group meals, and a back deck and side-yard tennis court make for ample opportunities to soak up the nature. Set on a private drive, the house is just a 5-minute walk to the beach, past beautiful cranberry bogs. Even though we were there in the early spring rather than prime beach-going weather, our time spent outdoors was time well spent--quiet, calm, and relaxing. We can't wait to go back.

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$229

20 Chadwell Ave

Sandwich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Convenient location and great fenced in yard” We enjoyed being able to bring our dog and the very large fenced in yard was perfect for her. The location of the home is great and close to the store and anywhere else you want to travel to. The house needs to be aired out and freshened up a bit. I didn't feel I could use the dressers because of the musty smells. It did have all the necessities of home for cooking and cleaning so that was great.

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$257

18 Great Hill Rd.

Sandwich house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$171

Quarterboard 4

East Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$120

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

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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$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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$264

GREAT VACATION HOUSE-GREAT LOCATION TO SOUTH BEACH

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$344

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$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 26 minutes

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$229

High-end Brewster ,Mass. Bay view town home

Brewster apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$409

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

Falmouth apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$172

Clean, comfortable ranch with lots of amenities

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$544

Great Martha's Vineyard Island Cottage!

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$344

Great Family Home, Close to South Beach, And Town

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$344

Vineyard House - South Beach Down The Street

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$344

Katama House "CLOSE TO THE BEACH"

Acushnet house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$311

“A thoroughly enjoyably experience!” Dave was wonderful to work with and offered advise on where some of the best areas to kayak might be found... saw several ospreys and other wildlife. The cottage has all new appliances and was clean. Sitting on the waterfront in the morning with coffee and the afternoon with a toddy was a great way to start and end each day.

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Price per night from

$344

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