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Shelter Island Waterfront Vacation Rentals(30)

30 Results
  • 5 BR,
  • 3 BA,
  • Sleeps 10
7 night min stay
(9)
  • 4 BR,
  • 3 BA,
  • Sleeps 7
3 - 14 night min stay
(4)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
14 night min stay
1 Review
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 14 night min stay
1 Review
$5,000 - $5,833
per week
14 - 31 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
14 - 31 night min stay
$2,350
per week
7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night min stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
3 - 7 night min stay
(7)
  • 5 BR,
  • 2 BA,
  • Sleeps 12
7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
7 night min stay
(6)
$325 - $564
per night
2 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 7 night min stay
(6)
$750 - $929
per night
13 - 30 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
13 - 30 night min stay
$500 - $600
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 9
5 night min stay
1 Review
  • 5 BR,
  • 3 BA,
  • Sleeps 10
14 night min stay
14 more choices from the HomeAway Network
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
3 night min stay
(12)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
6 night min stay
1 Review
$900 - $1,167
per night
15 night min stay
  • 5 BR,
  • 2 BA,
  • Sleeps 9
15 night min stay
(3)
$500
per night
3 - 31 night min stay
  • 5 BR,
  • 2 BA,
  • Sleeps 9
3 - 31 night min stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 12
(5)
  • 3 BR,
  • Sleeps 8
3 - 7 night min stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 7 night min stay
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 16
14 night min stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 7
3 night min stay
1 Review
  • Studio,
  • 1 BA,
  • Sleeps 14
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(6)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
7 night min stay
$45,000 - $100,000
per month
30 - 90 night min stay
  • 3 BR,
  • 4 BA,
  • Sleeps 6
30 - 90 night min stay
$2,000 - $3,300
per week
7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
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Recent Shelter Island Reviews

Best Service Provider !!

5 of 5
Shelter Island Hideaway offers luxurious accommodation in a truly natural setting. It clean, serene, comes with a Jacuzzi, pool, and private beach across the road. It’s a true piece of paradise for any discerning vacationer.
  • Submitted: Apr 10, 2015
  • Stayed: Feb 2015

It’s wonderful

4 of 5
It’s wonderful to know that Shelter Island Hideaway has everything you need in a vacation rental. You get the best of both nature and the relaxation of a spa. The walk to the beach is a short one while the multitude of windows is enough to tickle your senses even when you remain indoors.
  • Submitted: Apr 9, 2015
  • Stayed: Mar 2015

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