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Shelter Island Vacation Rentals(63)

63 Results
  • 5 BR,
  • 3 BA,
  • Sleeps 10
7 night min stay
(9)
  • 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,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
14 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
  • 6 BR,
  • 4 BA,
  • Sleeps 12
3 - 5 night min stay
2 Reviews
  • 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 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 night min stay
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 - 28 night min stay
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 30 night min stay
(5)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
(4)
$2,350
per week
7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night min stay
(4)
  • 5 BR,
  • 4 BA,
  • Sleeps 10
3 - 7 night min stay
(7)
$500 - $575
per night
2 - 6 night min stay
  • 4 BR,
  • 1 BA,
  • Sleeps 8
2 - 6 night min stay
1 Review
$257 - $536
per night
5 - 30 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 30 night min stay
(3)
$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
$325 - $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,
  • 1 BA,
  • Sleeps 6
(6)
$750 - $929
per night
13 - 30 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
13 - 30 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 7
14 night min stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(3)
  • 4 BR,
  • 3 BA,
  • Sleeps 9
3 - 31 night min stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 8
37 more choices from the HomeAway Network
$3,600 - $4,300
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 5
7 night min stay
(4)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
3 night min stay
(12)
$2,002 - $4,004
per week
7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 night min stay
(4)
$1,300 - $2,050
per week
7 - 14 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
7 - 14 night min stay
2 Reviews
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Recent Shelter Island Reviews

Absolutely perfect getaway

5 of 5
Our weeklong stay was simply perfect. The house is lovely from top to bottom. I LOVED the lap pool. The pictures just don't do this home justice. Staying here feels like true indoor/outdoor living. The natural light is incredible and when the sliding doors are open, and you get a really nice cross breeze. It's close to the downtown Shelter Heights district with restaurants and shops and there's a quiet beach within walking or biking distance from the house. I really loved getting cocktails at Sunset Beach (at sunset of course) and Rams Head Inn brunch's lobster benedict was impeccable (also only a five minute drive from the house). About half of the nights, we fired up the grill and ate on the back deck, which was a nice feature. Right down the road, there's also this fantastic little mini golf place that's super kitschy but fun. Overall, this property was the perfect getaway for our Shelter Island vaca. I would highly recommend it to anyone traveling or summering on the Island.
  • Submitted: Apr 19, 2015
  • Stayed: Aug 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