Dappled Sunlight
8 guests
4 bedrooms
Northwest Harbor, East Hampton
Make like a New Yorker and escape to the famous Hamptons. This home has everything you could need for an effortless, laidback break from the city.
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Home spotlights in Shelter Island
The Golden Dawn
4 guests
2 bedrooms
Litchfield, Litchfield County
There are some homes that simply capture your heart from the moment you arrive. And we won’t be surprised if it’s love at first sight when you see this charming Colonial saltbox house.
Hitchbrook
6 guests
3 bedrooms
Sharon, Litchfield County
Built in 1800, Hitchbrook is a quintessential New England home. Surrounded by farmland and rolling hills, this home is a private getaway for those looking for a pastoral retreat.
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 Airbnb Alternatives
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Airbnb is a shot in the dark. We meticulously vet all our homes in Shelter Island to ensure you won’t waste your precious holiday. Every home you'll find on Plum Guide comes fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Before being accepted into our collection, each home much pass a meticulous vetting process, culminating in a personal home visit from an independent Home Critic. Rent one of Plum Guide's luxury Shelter Island Airbnb Alternatives, and enjoy a long or short stay to remember. Should you need any assistance with your booking, our friendly team of experts will be on hand to guide you through the process.
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