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Shelter Island Vacation Rentals with Air Conditioning(83)

83 Results
  • 5 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
(9)
  • 6 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 12
$10,000 - $27,000
per month
30 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 5
30 night minimum stay
$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
$5,600 - $5,950
per week
7 - 31 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 12
7 - 31 night minimum stay
1 Review
$12,500 - $25,000
per month
30 - 31 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
30 - 31 night minimum stay
(3)
  • 6 BR,
  • 7 BA,
  • Sleeps 14
(8)
  • 3 BR,
  • 3 BA,
  • Sleeps 7
14 night minimum stay
(4)
  • 4 BR,
  • 3 BA,
  • Sleeps 7
4 night minimum stay
(4)
$22,000 - $25,000
per month
30 night minimum stay
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 12
30 night minimum stay
(5)
$16,500
per month
14 - 30 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
14 - 30 night minimum stay
$425 - $575
per night
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 night minimum stay
(4)
  • 6 BR,
  • 4 BA,
  • Sleeps 14
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 28 night minimum stay
1 Review
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
1 Review
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
14 night minimum stay
1 Review
$500 - $600
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(3)
$22,500 - $25,000
per month
30 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
30 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
  • 5 BR,
  • 4 BA,
  • Sleeps 10
(4)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(4)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
1 Review
  • 5 BR,
  • 2 BA,
  • Sleeps 12
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(3)
$500 - $1,000
per night
3 - 31 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 9
3 - 31 night minimum stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 8
  • 3 BR,
  • 3 BA,
  • Sleeps 6
$3,000
per week
14 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 3
14 night minimum stay
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Recent Shelter Island Reviews

Everything in the photos - and so much more!

5 of 5
This property is just absolutely stunning and so wonderful. My husband and I got married on Shelter Island and stayed here for 4 nights during our wedding weekend. We had countless numbers of family and friends filtering in and out throughout those days, and the size was more than accommodating. There are so many different spaces for different groups to socialize in, and we just had a blast. And nobody could get over what a beautiful property it was! It’s so well suited and fun for guests of any age, and every single room inside (there are many!), as well as the pool and the grounds outside are so well kept and spotless. And huge! Little touches like the amazing sound system, the on-site laundry services, all of the kitchen amenities, and the bikes in the garage just make you feel even more at home. And the beautiful porches both upstairs and downstairs are so perfect for relaxing. I enjoyed my coffee every morning on the upstairs balcony with a view of the water. The house is also on such a beautiful and quiet block only steps away from the beach, with the occasional deer families stopping by the front lawn. We just had the most fantastic and memorable few days on Shelter Island, and this house was integral to our good time. Andrew was also always so responsive and helpful in answering all of my questions both before our stay, and during. I can’t thank you enough for sharing your beautiful home with us Andrew! We will be back!
  • Submitted: Sep 29, 2014
  • Stayed: Sep 2014

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