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Shelter Island Vacation Rentals with Online Booking(24)

24 Results
14 - 30 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
14 - 30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
  • 5 BR,
  • 3 BA,
  • Sleeps 10
2 - 3 night minimum stay
  • 6 BR,
  • 7 BA,
  • Sleeps 14
(7)
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(3)
$2,275 - $3,500
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(3)
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
1 Review
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 - 14 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
1 Review
6 - 28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
1 Review
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
1 Review
31 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
  • 6 BR,
  • 4 BA,
  • Sleeps 14
2 Reviews
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
(5)
$2,002 - $4,004
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
(3)
4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 7 night minimum stay
  • 3 BR,
  • Sleeps 5
$1,700
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
1 Review
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Recent Shelter Island Reviews

BEAUTIFUL, CHARMING HOME

5 of 5
We had the pleasure of spending 10 wonderful days at this fully updated, charming farmhouse. The house was extremely well maintained and the English gardens are spectacular. The beds were extremely comfortable, with crisp white bedding and the kitchen was well stocked. The children spent hours in the large, private pool. The home is extremely well located to walk to sunset (crescent) beach and Shelter Island Heights and is also close to the central part of town. There are so many great things to do in Shelter Island: beach, hiking, biking, kayaking, mini-golf, farmer's market, great restaurants and all of it was just minutes away. The owner was very responsive and helpful and made us feel at home. We would love to rent this house again.
  • Submitted: Jul 9, 2014
  • Stayed: Jun 2014

STUNNING, FABULOUS LOCATION, GREAT HOUSE

5 of 5
What can I say except I am VERY picky when it comes to rental homes and this property is even better in person than any picture would do it justice, and it hands down beat my high expectations. Each room has been decorated in stunning furnishings, lighting, the right balance of classic and modern. The screened in porch was a great place to start the day with coffee and baked goods purchased on the island, and NOTHING beats getting on the ferry for the short crossing, its like all the stress goes away. I will for sure be renting this property again!
  • Submitted: May 6, 2014
  • Stayed: May 2014

ABSOLUTELY STUNNING!!

5 of 5
Beautiful light filled house, wonderfully decorated, all the comforts of home, close to the water and yet minutes to the shops and harbor cafes! We couldn't have wished for more, and can't reccomend it highly enough. Jane and Benjamin
  • Submitted: Apr 25, 2014
  • Stayed: Apr 2014