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.

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Reminiscent of something from a Laura Ingalls Wilder novel, this picturesque cabin is a haven surrounded by peace and quiet and lush woodland. Although you can count on a serene stay here, you’re also just a five-minute drive from the quaint town of Old Chatham where you can find some local amenities, or a ten-minute drive from Chatham Town, which has several excellent restaurants and plenty of charming local shops.

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.

Technicolour Dreamland

Technicolour Dreamland

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

This colourful Hamptons home has a laid back, friendly feel that would be perfect for a group of friends or family. In a quiet part of the Northwest Woods area of East Hampton, the house is surrounded by trees which guarantees peace, quiet and privacy to enjoy your trip.


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

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

Pine's Reach

Pine's Reach

  • 10 guests

  • 3 bedrooms

Walton Park, Chester

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

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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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