Shelter Island Two Bedroom Homes

We selected the 580 homes worth renting in this location

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Home spotlights in Shelter Island

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Set across seven private acres on Shelter Island’s Menantic Peninsula, this waterside property epitomises tranquillity. Wake up to views on one of the home's two private balconies, before whipping up breakfast in the state-of-the-art kitchen and sipping your morning coffee as you paddle in the sea.

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

If you need a base for a friendly get-together or a family reunion, then look no further than this abode in the heart of Westchester County. Thanks to the games room, gym and cinema room, there’s never a dull moment here – and that’s just what’s inside the home.

Whale Watching

Whale Watching

  • 8 guests

  • 4 bedrooms

Sag Harbor, Southampton

Arriving at this effortlessly chic seaside home from the city is a shockingly swift affair – you can be in Manhattan for breakfast and Sag Harbour for lunch. With its white-washed interiors and beachy accents, the home is ideal for a family of weekenders or those looking for a long-term change of scenery.

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Minutes away from East Hampton Village, this beautiful Sag Harbor home is ideal for sun worshippers and golfers alike. The Sag Harbor Golf Course is a stone's throw, and Havens Beach, among others, is reachable by car in minutes.


We selected the top 3% holiday homes in Shelter Island Two Bedroom Homes

Explore the 580 most perfect homes in our collection

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Most popular homes in Shelter Island

Technicolour Dreamland

Technicolour Dreamland

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

When In Bloom

When In Bloom

  • 6 guests

  • 3 bedrooms

Southampton, The Hamptons

Pine's Reach

Pine's Reach

  • 10 guests

  • 3 bedrooms

Walton Park, Chester

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

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Frequently asked questions

Spacious 2 bedroom homes in Shelter Island. Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short or extended stay in the best 2 bedroom homes that Shelter Island has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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