Vacation Rentals & Homes in Sag Harbor

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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

$687

East Hampton/Sag Harbor Village Fringe

Sag Harbor house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$3,442

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Price per night from

$987

Sag Harbor Village Fringe, Great Location

Sag Harbor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$2,289

The Seashell House

Sag Harbor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$975

no longer avail property Sold !

Sag Harbor cottage

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,033

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

Why Share? Beautiful guest house! Hamptons - Sag Harbor

Sag Harbor guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$401

Great rentals within 20 miles that match your search

Brand New Southampton Condo

Southampton condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$493

A One Of A Kind Beach Vacation Rental

Montauk house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$1,033

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

Airy, Woodsy, Walk to Beach, New Saltwater Pool!

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$1,066

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

East Hampton Summer Rental

East Hampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$1,148

Architect Designed Home in Waterfront Village

Greenport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$410

Ready for Summer 2021

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,721

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

Fantasy Bay Front Country French Villa

Southampton villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$2,295

Hip & Stylish East Hampton Getaway

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Airy & beautiful home!” We had a wonderful stay at this beautiful East Hampton home. The floor plan is open and makes for an easy flow between the airy living space and kitchen and dining area. The bedrooms are large and well appointed with comfortable beds and fresh linens. The setting of the house is on a wooded acre with incredible views out over the trees and the swimming pool below. The huge deck affords an outdoor dining area perfect for summer entertaining. We will definitely be back for another visit to this amazing get away.

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Price per night from

$984

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. 3 hours 16 minutes

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Price per night from

$1,393

Great Rates in 2019- No Increases In Rates and Over Holiday Weeks

Hampton Bays house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great time in Hamptons” Jackie and al's place is in a great location. Block away from the canal. Minutes away from the beach. Very Nice house. Looking forward to next summer.

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Price per night from

$459

Classic Hamptons Home in beautiful Water Mill - Minimum 2 week rental

Water Mill house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 13

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Price per night from

$1,721

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Price per night from

$780

Spectacular Family Resort in Hampton Bays, NY

Hampton Bays house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 3 hours 16 minutes

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Price per night from

$852

Waterfront Condo C204 at The Cliffside Resort

Greenport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$459

East Hampton shingle style home

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$861

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

Beautiful Estate home in the Hamptons, New York

Water Mill villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 10

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Price per night from

$6,883

Amagansett Estate 5 Bedroom 60ft Pool

Amagansett villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$1,606

Bishops Pond Southampton NY

Southampton townhouse

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 8

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Price per night from

$147

SOUTHAMPTON NEW YOK LUXURY RENTAL

Southampton house

  • 4 bedrooms
  • 11 bathrooms
  • sleeps 8

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Price per night from

$2,049

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,377

Southampton Water Front Retreat

Southampton cottage

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 10

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Price per night from

$3,278

Amagansett House with Pool near Village & Beach

Amagansett house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,312

SOUTHAMPTON POOL & TENNIS

Southampton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$3,278

Viewing 38 of 95
rentals in Sag Harbor

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