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Shelter Island Vacation Rentals(93)

93 Results
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
14 night min stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 7
3 - 14 night min stay
(4)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night min stay
(6)
  • 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,
  • 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
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night min stay
  • 6 BR,
  • 7 BA,
  • Sleeps 14
3 night min stay
(8)
$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 10
3 - 28 night min stay
1 Review
$2,275
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 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
$335 - $564
per night
2 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 7 night min stay
(6)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night min stay
$1,500 - $3,500
per week
7 - 31 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
7 - 31 night min stay
$2,650 - $6,250
per week
7 - 14 night min stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 14 night min stay
1 Review
  • 5 BR,
  • 2 BA,
  • Sleeps 12
7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
7 night min stay
(6)
$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
$2,350
per week
7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night min stay
(4)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 - 30 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

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