Shelter Island Homes for a Fishing Holiday

We selected the 914 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Shelter Island

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

An idyllic escape for all the family, this waterfront home sits in the hamlet of North Sea, part of larger Southhampton, and within an easy drive of a wide selection of restaurants, boutique shops and beautiful beaches. Whether you're here for a weekend or a longer stay, you'll immediately feel relaxed in this quiet spot, surrounded by nature.

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

If you’re in search of a coastal adventure or a relaxing beachfront escape, this home delivers the perfect solution. Nestled in Stonington village, you’ll be spoiled by beautiful views, an expansive two acres of lush grounds, a private pool and a tennis court.

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.

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Escape the frenetic pace of daily life and revel in an unmissable opportunity to relax and recharge at this stunning Shelter Island getaway. Set on a quiet tree-lined street and just a ten-minute walk from the pebble-strewn seashore, the home is perfectly set up for family holidays and weekend retreats with friends.


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

Explore the 914 most perfect homes in our collection

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Most popular homes in Shelter Island

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

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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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