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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

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

  • Home base for grandaughter's wedding

    "We had a lovely time in this very convenient home. Lois met us on arrival on Monday afternoon and returned the following Monday to wish us well on our return to California. Because the house is on several levels, it was a great choice for those who wished to rise early (we saw the swans out on the creek) and for those who wished to "sleep-in". The pool was wonderful and enjoyed by all. The creek was fun for tubing and paddle-boating. Part of our family stayed in this house and part of the extended family had another vrbo house a couple of miles away. One evening we had dinner for 24 out on deck and up by the pool, and there were dishes and silverware for all. Weather was lovely all week. The rehearsal dinner was at the Yacht club, the wedding was in garden at Sylvester Manor with dinner in a large "circus" tent in the meadow near Gardiner Creek, and the brunch on Sunday after the wedding was served from "Rolling in Dough" food truck (lots of fun with great pizza). My granddaughter was a beautiful bride and we all had a wonderful time. I would recommend this house for a big family gathering or for a small retreat time. We did not have time to read any of Leon Uris' books, but I had read several of them previously. The owners have very eclectic taste and some great posters. So glad I found this property."
    Guest: Grandma Sue Date of Stay: July 2014 Review Submitted: August 13, 2014
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  • This house made our family wedding weekend perfect!

    "We stayed at this home for 4 nights for a family wedding on Shelter Island in mid-September. From the moment we arrived, the house was perfect: we had a large party - several couples, a young child, several adults who wanted their own sleeping spaces - and the house was perfect for accommodating everyone. Moreover, its central but somewhat secluded location, gorgeous water view and ample outdoor seating, not to mention the indoor pool, made it an ideal place for a large family gathering. This house made our wonderful wedding weekend that much more wonderful! Thank you!"
    Guest: LHBLK Date of Stay: September 2014 Review Submitted: October 1, 2014
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  • Shelter Island a magical island experience.

    "This lovely home in a prime location , just next to a private beach with tennis court provided a lovely base for our magical time on shelter island. The house was in a very quiet area, in fact for the week we never heard a siren, car or anything other then the lovely sound of the water, birds and nature. The house was well equipped with all the essentials needed to stay and cook. We cooked or grilled at the house every day, we brought our own bikes for some of the best riding i have ever done. If you are looking for a quiet serene, comfortable place to stay this is a great choice. The owner was available as needed for any questions we had. thanks david we will be back!!!!!!"
    Guest: 10isgal Date of Stay: June 2014 Review Submitted: June 26, 2014
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  • Shelter Island

    "We leased 4 homes on Shelter Island to accommodate family and friends for a wedding. Of the 4, this home was by far the most popular because it was just so livable. We had every bedroom filled with ages 22 - 28 and the guest cottage with a father in his early 70s. The top floor of the main house lends itself to socialization; the fireplace creates its own ambience; there are ample baths for everyone. It's just a fun house; the rest were all more than adequate but stiff, wooden, and formal. This house is just the opposite. It's for fun!"
    Guest: Chris Date of Stay: September 2014 Review Submitted: October 4, 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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