Book Luxury Wedding House Rentals in Shelter Island

We selected the 902 homes worth renting in this location

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Home spotlights in Shelter Island

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

Wander Inn is an architect-renovated ranch in a beautiful setting. Built in the sixties, this home is made for relaxation and indulgence.

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

It’s no wonder why a multitude of actors, composers, and artists have hideaways in the Berkshires. This classic Berkshires home, originally built as a schoolhouse in 1866, is steeped in history and rural charm.

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

Pack your bags and gather your favourite friends or family members, it's high time for a trip to the Hamptons. Just A Minute is a comfortable and modern home with easy access to Southhampton, where you can find everything you need from retail therapy to white sandy beaches.

Pine's Reach

Pine's Reach

  • 10 guests

  • 3 bedrooms

Walton Park, Chester

It's back to camp at this lakeside home, which has been designed to make the most of its beautiful surroundings. Wooden floorboards, adjoining cabins, folding doors, and outdoor walkways give the sense of being in a giant – and rather quirky – treehouse.


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

Explore the 902 most perfect homes in our collection

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Most popular homes in Shelter Island

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

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

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

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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