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VRBO is part of the HomeAway family, the world leader in vacation rentals with over 1 million listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More

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This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation

Recent Shelter Island reviews

  • Charming Cottage and Terrific Owners

    "We had a wonderful multi-week stay here. The house is as charming as advertised. We swam off the dock every day. Also kept my 20' sailboat at the dock and had great fun sailing in Gardner's bay. Topping it all off, the owners were a delight to deal with as we settled in and got our bearings. If you're considering this property give it a go, you'll be glad you did!"
    Guest: Ellen Date of Stay: June 2014 Review Submitted: August 25, 2014
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  • Wonderful place

    "Beautiful and very comfortable house. Cherry on the cake : the house is deeply clean and Maureen, the owner, very nice and helpful. We spent a relaxing stay in this quiet place."
    Guest: Pascale P. Date of Stay: May 2014 Review Submitted: May 27, 2014
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  • Fabulous Stay

    "Had a great time in charming home on Shelter Island. It was perfect for my husband, and parents. We enjoyed all the amenities the house offered, including great backyard, deck and grill. Perfectly located on the island, with easy access to beaches and restaurants. Can't wait for next year!!!"
    Guest: Melissa G Date of Stay: July 2014 Review Submitted: August 6, 2014
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  • Perfect Vacation

    "The house was perfect . Renting was simple and easy with lots of recommendations of places to visit . Very clean. Beds were comfortable with lots of towels and blankets . Our favorite place was the deck . We had breakfast and dinner on the deck each day . Nice view of the water but grassy property was just as nice . Walked to The Mashamack Preserve from the beach. It was an amazing walk and the kids loved exploring the beach . We tried the out door shower. water was hot but still too chilly out side for it each night. We found plenty of pots and pans for cooking breakfast and dinner each night. we even baked cup cakes with all the equipment there to use .The grill was perfect for the burgers and hot dogs . very quite beach . If you want company and to meet new people this is not the beach to do it on . very good price for the house . We will rent again when going visit Greenport and wineries. too."
    Guest: 2girls320 Date of Stay: May 2014 Review Submitted: June 6, 2014
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Shelter Island Travel Tips

You Will Love Shelter Island Vacation Rentals

Shelter Island vacation rentals are so great, you will recommend them to friends for years after your visit to the area! From adorable shack-like cafes to charming mom n' pop restaurants, you will find unique establishments in Shelter Island that are unlike anything you have experienced before! Enjoy a day strolling along the waterfront, observing the native wildlife, or visit the Mashomack Preserve to see 2,100 acres of Nature Conservancy. Either way, you will be touched by the efforts of the locals to preserve the natural elegance and charm of their neighborhood.

Summer Homes in Shelter Island Couldn't Be More Lovely

Summer homes in Shelter Island are so lovely, they could not be improved upon. Enjoy great beaches like Sailors' Haven, for days of sunbathing and picnicking on the sand, or spend your days indoors. The great thing about Shelter Island summer homes is that you can relax, enjoy the privacy, and spend time working on your novel or catching up on letter writing. Take a day trip to Long Island for hip clubs, five star restaurants, and high-end shopping, or stroll through The Hamptons star watching for frequent visitors like Gwyneth Paltrow and Jerry Seinfeld.

House Rentals in The Hamptons Are Something You'll Never Forget

House rentals in The Hamptons are not just a place to live for a few weeks each summer, they're an experience that you will remember forever. Rub elbows with celebrities like Paul McCartney, or get away from the crowds and visit Dead Man's Hill on Corona Avenue. Go clamming on the beach, or pick raspberries inland. There are quaint activities to be done in Shelter Island, and all over The Hamptons, that will make you feel relaxed and happy. You will love your trip to The Hamptons, and always remember it as the place where you had the best peaches in the world!

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