Shelter Island Homes for a Fishing Holiday

We selected the 918 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

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Pets

An extra fee may apply

0

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.

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.

Swan's Nest

Swan's Nest

  • 7 guests

  • 4 bedrooms

Bridgehampton, Southampton

You don't even need to step out of this home to take in the view of Sam’s Creek and Mecox Bay, with the sea stretching out in the distance. At this cottage by the water, built up on stilts, you’ll be able to watch it all from the comfort of home.

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Sea Aster sits in an ideal spot for exploring beach and town life. Sag Harbor Main Street, with its restaurants, boutiques and artisan bakeries, is less than fifteen minutes’ walk away, and you can get to Haven’s Beach – a perfect spot to watch the sun set – in ten.


We selected the top 3% holiday homes in Shelter Island Homes for a Fishing Holiday

Explore the 918 most perfect homes in our collection

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Most popular homes in Shelter Island

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

The Mortar & Pestle

The Mortar & Pestle

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

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Check upcoming rates & availability for Shelter Island Homes for a Fishing Holiday


Frequently asked questions

Discover our collection of home for a fishing holiday in Shelter Island. All of our Plum Guide homes are fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included, so all you have to worry about is remembering the bait. Book your trip to Shelter Island today and enjoy staying in one of our best fishing holiday homes. Our friendly team of experts is on hand 24/7 if you need anything.

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