Rent Boutique Hotel Alternatives in Shelter Island

We selected the 936 homes worth renting in this location

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Age 13+

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Children

Age 1 to 12

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Pets

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Home spotlights in Shelter Island

Magic in The Hamptons

Magic in The Hamptons

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

This beautiful home is set within dense woodland on the northern East Hampton Coast, just two blocks from a private beach looking out over Gardiners Bay. Inside, there are beautiful hardwood floors, a cosy fireplace for cool evenings and cathedral-like ceilings over the dining area.

Technicolour Dreamland

Technicolour Dreamland

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

This colourful Hamptons home has a laid back, friendly feel that would be perfect for a group of friends or family. In a quiet part of the Northwest Woods area of East Hampton, the house is surrounded by trees which guarantees peace, quiet and privacy to enjoy your trip.

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Built in 1800, Hitchbrook is a quintessential New England home. Surrounded by farmland and rolling hills, this home is a private getaway for those looking for a pastoral retreat.

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Set within an acre of lush green grounds, this seriously charming home is just a twenty-minute drive from the centre of Sag Harbour - undoubtedly one of New York State's best-kept secrets. This centuries-old seaside village may be known as one of the most family-friendly places in the Hamptons, but its strictly adults-only activities include a visit to the nearby Wölffer Estate vineyards to sample their famed rosé cider.


We selected the top 3% holiday homes in Shelter Island Boutique Hotel Alternatives

Explore the 936 most perfect homes in our collection

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Most popular homes in Shelter Island

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

Whale Watching

Whale Watching

  • 8 guests

  • 4 bedrooms

Sag Harbor, Southampton

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

When In Bloom

When In Bloom

  • 6 guests

  • 3 bedrooms

Southampton, The Hamptons

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

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Frequently asked questions

If you're on the hunt for the finest Boutique Apartment Rentals on offer in Shelter Island, then you've come to the right place. We are meticulous in our approach here at Plum Guide, accepting only the top 3% of homes in any given location, so explore our exclusive range today. Every home you see has been systematically reviewed, and comes fully furnished with all linens and essential bathroom toiletries included, as well as an expertly-equipped kitchen. Stay in one of the most remarkable Shelter Island Boutique Hotel Alternatives, and guarantee yourself a trip to remember. Don't hesitate to contact our team of experts either, because they love nothing more than helping you discover your dream home.

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