Shelter Island Bed and Breakfast Alternatives

We selected the 928 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Shelter Island

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

This quintessential clapboard home in Sag Harbor is sure to pique the interest of travellers looking for a relaxing stay in the Hamptons. With its close proximity to the coast, including Haven's beach, the home is conveniently located for exploring the area.

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

A luxurious harbour-front villa overlooking the serene Noyack Bay, this home's stylish interior boasts elegance and sophistication. Huge, panoramic windows display the beautiful surroundings while flooding the space with light.

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

This NYT-featured Catskills home is not quite the cabin it seems to be. What looks like a single storey home from one angle is actually built over a creekside slope, and we think it's one of the most interesting places we've seen for a peaceful stay in the woods.

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.


We selected the top 3% holiday homes in Shelter Island Bed and Breakfast Alternatives

Explore the 928 most perfect homes in our collection

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Most popular homes in Shelter Island

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

When In Bloom

When In Bloom

  • 6 guests

  • 3 bedrooms

Southampton, The Hamptons

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

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Check upcoming rates & availability for Shelter Island Bed and Breakfast Alternatives


Frequently asked questions

Looking for bed and breakfast style accommodation 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 bed and breakfasts 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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