Book Luxury Wedding House Rentals in Shelter Island

We selected the 920 homes worth renting in this location

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Home spotlights in Shelter Island

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.

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

This home's architecture, interiors and colourful prints all share a mid-century modern style, but its woodland surroundings are more Hansel and Gretel than Gilbert and George. In a tiny hamlet in upstate New York, it’s surrounded by mountains, lakes and forest – great for skiers, hikers and wild swimmers alike.

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

If you need a base for a friendly get-together or a family reunion, then look no further than this abode in the heart of Westchester County. Thanks to the games room, gym and cinema room, there’s never a dull moment here – and that’s just what’s inside the home.

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

This delightful cottage, nestled in the picturesque mountains of New York State’s famous Shawangunk Ridge, is an ideal spot for a cosy country escape. As the last property before the entrance to a protected nature reserve, this home offers unmatched tranquillity and proximity to nature.


We selected the top 3% holiday homes in Shelter Island Wedding House Rentals

Explore the 920 most perfect homes in our collection

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Most popular homes in Shelter Island

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Cottontail Creek

Cottontail Creek

  • 4 guests

  • 2 bedrooms

Shandaken, New York

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

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Check upcoming rates & availability for Shelter Island Wedding House Rentals


Frequently asked questions

Treat yourself to a luxury stay in one of the finest Wedding House Rentals that Shelter Island has to offer. Your special day deserves a special venue, so book your stay today for the experience of a lifetime. Here at Plum Guide, we are meticulous in our approach, testing everything in a home from Wifi speed to a space's design, so no stones are left unturned in our pursuit for perfection. Each listing in our collection comes fully furnished too, with a brilliantly-equipped kitchen, essential bathroom toiletries, and all linen included. Reserve one of the top Private Homes to Rent for a Wedding in Shelter Island today, and celebrate in style. Get in touch with our team of experts, who can guide you through the booking process and ensure that the home you choose is absolutely perfect for you and your loved ones.

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