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Shelter Island Waterfront Vacation Rentals Vacation Rentals(31)

31 Results
  • 5 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
(9)
$357 - $893
per night
3 - 14 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 14 night minimum stay
1 Review
$5,000
per week
14 - 30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
14 - 30 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(4)
  • 4 BR,
  • 3 BA,
  • Sleeps 7
4 night minimum stay
(4)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
14 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night minimum stay
$500 - $600
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night minimum stay
$22,500 - $25,000
per month
30 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
30 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
(4)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
1 Review
  • 5 BR,
  • 2 BA,
  • Sleeps 12
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
(6)
$500 - $1,000
per night
3 - 31 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 9
3 - 31 night minimum stay
1 Review
  • 3 BR,
  • 3 BA,
  • Sleeps 6
16 more choices from the HomeAway Network
$250 - $450
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
3 night minimum stay
(12)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
6 night minimum stay
1 Review
  • Studio,
  • 1 BA,
  • Sleeps 14
  • 5 BR,
  • 2 BA,
  • Sleeps 9
(3)
  • 3 BR,
  • Sleeps 8
3 - 7 night minimum stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 7
3 night minimum stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 12
(5)
$500
per night
3 - 31 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 9
3 - 31 night minimum stay
1 Review
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 16
14 night minimum stay
2 Reviews
$15,000
per month
30 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
30 night minimum stay
(3)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(6)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 7 night minimum stay
$750 - $2,250
per night
3 - 90 night minimum stay
  • 3 BR,
  • 4 BA,
  • Sleeps 6
3 - 90 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 9
1 Review
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Recent Shelter Island Reviews

It was overall a lovely

5 of 5
We had an ecstatic sojourn at the Shelter Island Cottage, nothing short of a beautiful experience. The beach house has got some stellar sights, especially its serene & huge Koi pond. We just fell in love with the whole place that looks not just quiet & secluded but gives you a wonderful Caribbean flair to reminisce. Our room was very comfortable and spacious – nattily arranged with sheer white sheets and a pristine look. It was overall a lovely and unforgettable experience.
  • Submitted: Sep 20, 2014
  • Stayed: Sep 2014

Beautiful Serene Retreat

5 of 5
The pictures don't capture what a lovely and surprising home this is nor how spectacular its setting. The landscaping, the views of the creek, the subtle winningness of the architecture...a great experience. We found the house warm and artfully arranged with stylish and comfortable furniture and good artwork. The overall effect is clean and organized but in an unfussy way, plus a great kitchen that would please a serious chef, all perfect for an enlightened beach house. It was such a treat to wake up to the dreamy views of the creek after a night of restful sleep on the exceptionally comfortable king-size bed. Though the weather during our stay was great - and there is plenty to do on Shelter Island/Hamptons - at times we enjoyed just lounging around the house and deck, reading, cooking, paddling around in the canoe & kayaks...we had to motivate ourselves to leave. On the one rainy day, we were happily occupied with various fun activities in the house - playing games, exercising in the basement workout room and browsing through the wonderful selection of movies on the Roku TV system. We can only imagine how cozy it would be to huddle around the fireplace in the winter months! Meanwhile, the location - minutes from ferry, beaches, shops and restaurants - could not be more convenient. The house is an easy 5-minute drive from the famed Vine Street Café and a short ferry ride away from wineries on the North Fork and the lovely, low-key town of Sag Harbor on the South Fork. The owners are super pleasant and accommodating. They left well-written notes detailing their home and Shelter Island attractions which certainly made our lives a lot easier. This is a dream of a vacation home. We look forward to our return.
  • Submitted: Sep 9, 2014
  • Stayed: Aug 2014

Charming Cottage and Terrific Owners

5 of 5
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!
  • Submitted: Aug 24, 2014
  • Stayed: Jun 2014