Rent Boutique Hotel Alternatives in Shelter Island

We selected the 936 homes worth renting in this location

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Home spotlights in Shelter Island

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

At the bottom of the garden, you’ve got direct access to the serene waters of Noyack Bay, with kayaks, paddleboards and bicycles provided by your host. It’s a fifteen to twenty-minute walk (or five-minute cycle) to the restaurants and grocery store of Noyack, just along the coast from Sag Harbour.

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Live your best East Hampton life at this light-filled, mid-century architectural gem, just a seven-minute drive from the beach. With its private pool and hot tub, grassy lawns backed by juniper trees for post-pool games (table tennis, anyone?

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

Nestled in the woodlands, this cabin provides cosy comfort and stylish charm. The outdoor area is the perfect place to keep toasty by the fire and eat delicious meals.

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

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

Whale Watching

Whale Watching

  • 8 guests

  • 4 bedrooms

Sag Harbor, Southampton

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

When In Bloom

When In Bloom

  • 6 guests

  • 3 bedrooms

Southampton, The Hamptons

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, North Fork

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

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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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