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Shelter Island Vacation Rentals with Parking Included(88)

88 Results
  • 5 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
(9)
  • 6 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 12
  • 5 BR,
  • 3 BA,
  • Sleeps 10
$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
$3,500 - $3,850
per week
14 - 30 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
14 - 30 night minimum stay
$450 - $898
per night
2 - 3 night minimum stay
  • 6 BR,
  • 7 BA,
  • Sleeps 14
2 - 3 night minimum stay
(8)
$12,500 - $25,000
per month
30 - 31 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
30 - 31 night minimum stay
(3)
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 12
4 night minimum stay
(5)
  • 4 BR,
  • 3 BA,
  • Sleeps 7
(4)
  • 3 BR,
  • 3 BA,
  • Sleeps 7
14 night minimum stay
(4)
$425 - $575
per night
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 8
6 - 28 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 - 30 night minimum stay
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(3)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(4)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
  • 5 BR,
  • Sleeps 12
3 - 7 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(3)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
14 night minimum stay
1 Review
$22,500 - $25,000
per month
30 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
30 night minimum stay
$335 - $395
per night
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 7 night minimum stay
1 Review
$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
3 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

Stunning House in Perfect Location

5 of 5
Thank you Jean-Sebastion. Your house and fittings were of a very high standard and contributed to a wonderful stay for the 6 of us. The house was very comfortable and in a nice quiet location. We loved Shelter Island, it is a unique environment and perfect location for our vacation from Australia to attend a family wedding.
  • Submitted: Sep 24, 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