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Shelter Island Vacation Rentals with Online Payment(42)

42 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
  • 6 BR,
  • 7 BA,
  • Sleeps 14
(8)
$425 - $575
per night
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 night minimum stay
(5)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 30 night minimum stay
(5)
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
1 Review
$2,275 - $2,450
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 28 night minimum stay
1 Review
$500 - $600
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night minimum stay
  • 6 BR,
  • 4 BA,
  • Sleeps 14
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(3)
$1,750 - $2,350
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
(4)
  • 3 BR,
  • 3 BA,
  • Sleeps 7
  • 5 BR,
  • 3 BA,
  • Sleeps 10
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
30 night minimum stay
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 8
  • 5 BR,
  • 2 BA,
  • Sleeps 12
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
  • 4 BR,
  • 3 BA,
  • Sleeps 8
20 more choices from the HomeAway Network
$3,600 - $4,300
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
(4)
$250 - $450
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
3 night minimum stay
(12)
$1,550 - $2,050
per week
7 - 14 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
7 - 14 night minimum stay
2 Reviews
$500 - $1,000
per night
1 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
1 - 7 night minimum stay
1 Review
$375 - $843
per night
3 - 7 night minimum stay
  • 3 BR,
  • 4 BA,
  • Sleeps 8
3 - 7 night minimum stay
$168 - $275
per night
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 7 night minimum stay
(21)
$2,002 - $4,004
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
(4)
$3,000 - $4,950
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(3)
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Recent Shelter Island Reviews

LOVELY HOME - WONDERFUL LOCATION!

4 of 5
Lovely views of the harbor and very close to restaurants, cafes and shops - A great house and it was very comfortable for our 'girlfriends' weekend, we were five women who enjoyed relaxing on the front porch chatting with a glass of wine - We did cook one meal and it was great to have access to fresh herbs and tomatoes from the garden in the yard - The caretaker, Tom, even brought us peppers from his own garden that were delicious - Thank you Tom! This is a 5-star property but I gave it a 4-star rating only because of the constant traffic in front of the house going to the ferry - We were there in October so it was considerably less than it must be in the summer months - Even after saying that, I would definitely stay there again! (One suggestion would be to have a full length mirror somewhere in the bedroom area)
  • Submitted: Oct 29, 2014
  • Stayed: Oct 2014

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