Ossipee Rentals

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131 Houses

Skip to beach! Condo across from beach!

Dennis Port condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 26 minutes

Match: Sea view

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Price per night from

$172

Ocean View Condo across from Beach with pool!

Dennis Port condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 26 minutes

Match: Sea view

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Price per night from

$172

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 18 minutes

Match: Sea view

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Price per night from

$245

Topside MainHouse

South Orleans house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Sea view

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Price per night from

$1,225

Condo: Ocean View Private Beach w/ Towels, Linens, Bedding and Air Conditioning

North Truro apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect for two couples” Great place for a one week stay! We went down there as two couples and we found it perfectly comfortable. The kitchen was nice, the den/second bedroom was comfortable, had a rustic feel to it and the master bedroom was very cozy. The bathrooms were a little small, only shower space, no bath, but perfect for a beach vacation. Not directly on the beach, but 30 second walk across the parking lot and right there. The view from the front is great, you do see the bay and you can see Provincetown lit up at night. It was a nice quiet place. Thank you so much Jean!

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Price per night from

$284

Palace / MerVeille

Biddeford cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$189

Hillside Ocean View 2BR with Private Beach Access

Ipswich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$189

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Price per night from

$281

Spectacular Private Waterfront and Beachfront Home

Wellfleet cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Unforgettable” Heaven on earth at Drew and Heather's ! Very pleasant house, with all facilities, and a hudge sundeck. High tide, and it's like a private pool at 30 ft. Low tide, and a wonderful sandbeach appears 6 hours for fantastic walks. Can you imagine nicer bike rides very early in the morning to PB's restaurant and baker at highway 6 (about 20 mn ), for a wonderful croissant breakfast ! So much to say about the stay at Wellfleet, Just come and see by yourself. It's sure, I'll be back (from France)

Match: Sea view

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Price per night from

$309

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Price per night from

$900

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.

Match: Sea view

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Price per night from

$629

Summer Rental - Marguerite- Biddeford Pool ME

Biddeford Pool cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Sea view

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Price per night from

$491

Private Safe Beach Community

Hampton apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Sea view

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Price per night from

$572

Family House on Short Sands at York Beach

York Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$401

AFFORDABLE WATER VIEW Cape Cod

Pocasset cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$172

REXHAME BEACH, MARSHFIELD, MA OCEANFRONT BUNGALOW

Marshfield bungalow

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Match: Sea view

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Price per night from

$595

Ocean Front Cottage, Harpswell, ME

Harpswell cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$253

Dune Tootin Unit 3

East Sandwich apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Wonderful!” Everything was wonderful, from the rental cottage to the weather.

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Price per night from

$186

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Price per night from

$229

Topside BoatHouse on Pleasant Bay

South Orleans boathouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$491

Cape Cod 2 BR Condo at the Beach August 5-12 !

Dennis Port hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Sea view

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Price per night from

$245

Beautiful Seaside Island Home

Long Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$458

Ocean Front Condo on Hampton Beach

Hampton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$327

Spacious, ocean view, residential beach cottage near historic Plymouth, MA

Plymouth cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

“Perfect location” Quaint cottage. Has Everything you need in the pantry to cook or grill. Porch is relaxing after a day at the private beach.

Match: Sea view

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Price per night from

$343

165 North Shore Blvd

East Sandwich cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Love the Two-Family Capability of This Property!” We stayed here the last week of June and it was fantastic! Our family of four (with two small sons) stayed in the side cabin while my in-laws stayed in the larger home. It couldn't have been more perfect. Both homes were immaculate and well-stocked (dishes, pots, pans, flatware) so we were able to cook full meals during our stay. Our favorite part of our week was the amazing beach. Our boys waited each day for the sandbars to appear, and then would spend hours playing ball and wading in the cold bay water. We appreciate the owners sharing their lovely property with us and would be honored to stay there again in the future!

Match: Sea view

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Price per night from

$310

Bohemia RETREAT Studio

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$258

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!

Match: Sea view

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Price per night from

$370

Oceanfront Condo with Awesome Views

Old Orchard Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$138

“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.

Match: Sea view

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Price per night from

$343

Slice of Paradise at Hampton Beach, NH

Hampton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Sea view

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Price per night from

$269

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!!! : )

Match: Sea view

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Price per night from

$279

Oceanside 2

East Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$200

GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM

Rockport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Match: Sea view

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Price per night from

$281

“Surf View” - Oceanfront

Hampton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Sea view

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Price per night from

$343

Waterfront, Quiet 3 BR Cape-Walk to Beach

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Sea view

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Price per night from

$629

Andy's Retreat - Heated outdoor pool, Hot Spring jacuzzi, central AC, BBQ

Falmouth house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$686

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.

Match: Sea view

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Price per night from

$210

Exclusive Lifestyle near the Ocean

Marblehead house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$916

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