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Shelter Island Rentals(81)

81 Results
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 14 night min stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 7
3 - 14 night min stay
(4)
  • 5 BR,
  • 3 BA,
  • Sleeps 10
7 night min stay
(9)
$5,000 - $7,800
per week
7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 night min stay
1 Review
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night min stay
(6)
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 14 night min stay
1 Review
$5,600 - $6,000
per week
7 - 31 night min stay
  • 5 BR,
  • 3 BA,
  • Sleeps 12
7 - 31 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
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night min stay
$12,500 - $25,000
per month
30 - 31 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
30 - 31 night min stay
(3)
$22,000 - $25,000
per month
30 night min stay
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 12
30 night min stay
(5)
$425 - $575
per night
2 - 6 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 6 night min stay
(6)
$500 - $575
per night
2 - 6 night min stay
  • 4 BR,
  • 1 BA,
  • Sleeps 8
2 - 6 night min stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(5)
  • 5 BR,
  • 4 BA,
  • Sleeps 10
3 - 7 night min stay
(7)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 night min stay
(4)
$350 - $571
per night
2 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 8
2 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night min stay
  • 5 BR,
  • 2 BA,
  • Sleeps 12
7 night min stay
$286 - $536
per night
4 - 30 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 30 night min stay
(3)
  • 6 BR,
  • 4 BA,
  • Sleeps 12
3 - 5 night min stay
2 Reviews
$750 - $929
per night
13 - 30 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
13 - 30 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 - 30 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(3)
  • 4 BR,
  • 3 BA,
  • Sleeps 9
5 night min stay
1 Review
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night min stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
7 - 14 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
30 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 7
14 night min stay
(4)
  • 5 BR,
  • 3 BA,
  • Sleeps 10
14 night min stay
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Recent Shelter Island Reviews

Perfect kid friendly getaway

5 of 5
We spent a week there last Summer with our two young children (4 and 1) and loved the house. Very spacious, with a nice playroom in the basement. The pool is gorgeous : big enough to swim and for children to have fun. It was spotless, well equipped (including for small children) and decorated with a lot of taste. With two small children we ended up spending a lot of time in and around the house and never got bored. The outside terrace and bbq are perfect for lunch and dinner by the pool. Also close to the beach, Sunset Beach (nice cocktails), Reddings (now Marie Effeil I think) for nice coffee, bread, cheese and viennoiseries. Mashomack Preserve nearby is gorgeous and they provide strollers for kids! You can also walk/jog to the beach from the house. Stefan and Sabrina are very nice, professional and responsive. All in all a perfect place to relax. So nice that we are planning to go back there this Summer with my sister and her family.
  • Submitted: Apr 24, 2015
  • Stayed: Sep 2014

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

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