Greenport Rentals

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45 Houses

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Waterfront Condo C204 at The Cliffside Resort

Greenport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$459

Great rentals within 20 miles that match your search

Very Private and Tranquil House in wooded estate.

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,148

Bright & clean summer rental plus beach pass two blocks from ocean beach

New London house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$332

Romantic Getaway in Southampton (private room/bathroom)

Southampton private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$356

Mint Southampton Village 5-BR South of the Highway w Heated Pool

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

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Price per night from

$1,721

Amagansett Estate 5 Bedroom 60ft Pool

Amagansett villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$1,607

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,377

SEASHELLS BY THE SEA SHORE

Hampton Bays house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

Responds fast! avg. 1 hour 30 minutes

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Price per night from

$1,221

Shorecrest Beach House, 4 bedroom private beach front, new renovation

Southold house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$917

Ready for Summer 2021

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,723

PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$431

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$1,664

Majestic Southampton Waterfront Estate

Southampton villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

“Incredible home” This was the perfect home for my husband, kids and grandkids. I can't begin to describe how incredible this home was. From the amazing outdoor kitchen, magnificent landscaping, the toasty warm huge pool, with seating enough for our supersized family of 20 with 4 grandbabies. This home was able to house us all comfortably. The inside of the house was clean, spacious and beautifully decorated. The high count sheets were a dream to sleep on (cute pun intended). The air conditioning was set to the perfect temperature. Every day all of us lived in the pool and at night enjoyed the gorgeous sunsets over the bay. To say we loved this home is an understatement. We are still all talking about the amazing vacation. The owner was really really nice to deal with and made us feel welcomed.

Responds fast! avg. 1 hour 30 minutes

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Price per night from

$1,394

Spectacular Family Resort in Hampton Bays, NY

Hampton Bays house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 1 hour 30 minutes

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Price per night from

$852

Amagansett Estate 3 BR 60ft Pool

Amagansett house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$1,148

Newly remodeled mid century modern

East Hampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$574

Quaint Seaside Retreat With Full Gym

Hampton Bays house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,377

Perfect vacation home minutes to bay and ocean beaches

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,434

Cottage european charm private beach in Southampton, North Sea

Southampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$541

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Price per night from

$987

Serene and peaceful beach getaway!

Hampton Bays house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$746

Vacation home in Artistic / Historic area of East Hampton, NY

Springs house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,530

piece of Heaven

Mattituck house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$1,721

Luxurious living on a bucolic alpaca farm

Lyme house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$230

Great 4 bedroom family home walking distance to the beach and village

Sag Harbor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,377

Responds fast! avg. 14 minutes

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Price per night from

$689

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Price per night from

$574

4BR Waterfront + Dock Family Retreat in Southampton

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 29 minutes

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Price per night from

$1,033

Chic 3 Bed Cottage w/Modern Pool, 5 Mins from Town

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$660

Harbor view oasis

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$2,378

Hamptons Getaway on the water with gorgeous sunsets

East Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$775

Southampton Village home/Heated Pool/July availability

Water Mill house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$2,639

Beech Tree Cottage

Sag Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“The cottage experience was relaxing and peaceful with a short wa” Enchanting cottage, very comfortable, enjoyed a little interaction with the owner's family and dog. Very sweet.

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Price per night from

$689

Peace Barn in the heart of the CT River Valley

Deep River house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$345

Shore Drive Oasis by the Bay

Waterford house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$343

Hamptons Lofty Beach Barn - Pet Friendly

Water Mill house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 38 minutes

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Price per night from

$1,721

Idyllic Getaway on the CT Shore - Quiet, Peaceful, Stylish

Westbrook house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$307

Magnificent private Southampton Estate

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$5,163

Viewing 38 of 45
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