Book Luxury Wedding House Rentals in Shelter Island

We selected the 914 homes worth renting in this location

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Home spotlights in Shelter Island

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Dating back to the eighteenth century, it’s safe to say that The Whaler’s Cottage is steeped in history. It has a wonderful garden with lots of room for relaxing, and the interiors are stunning.

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.

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Live your best East Hampton life at this light-filled, mid-century architectural gem, just a seven-minute drive from the beach. With its private pool and hot tub, grassy lawns backed by juniper trees for post-pool games (table tennis, anyone?

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.


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

Explore the 914 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

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

Cottontail Creek

Cottontail Creek

  • 4 guests

  • 2 bedrooms

Shandaken, New York

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

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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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