Shelter Island Holiday Homes

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Featured Holiday Homes in Shelter Island

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Holiday Accommodation Shelter Island

You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Shelter Island are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Shelter Island itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.

Shelter Island holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.

If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Shelter Island, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.

Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Shelter Island with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.

Shelter Island Holiday Homes essential information

Accommodation
1536 Holiday Homes
Lowest Price
NZ$134
Highest Price
NZ$857
Popular accommodation
Gorgeous private Hamptons house with pool and volleyball court, Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping, Waterfront Beach House, Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!, Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included, Unobstructed Ocean Views ! A Beautiful Montauk Getaway , Oceanfront Beach House lay in bed and hear the waves, boats , birds, Historic Essex Home w/ Large Yard Near Downtown!, Quaint Family-sized Home w/private beach — 5 minutes from wineries!, Northfork Townhouse- walk to all/ newly renovated, COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach, Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Top trending hotels in Shelter Island

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