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Shelter Island Rentals(8)

8 Results
$12,500 - $25,000
per month
30 - 31 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
30 - 31 night min stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 - 28 night min stay
1 Review
$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
$250 - $350
per night
2 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night min stay
(5)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
5 night min stay
(10)
$167 - $295
per night
3 - 31 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 31 night min stay
(4)
$22,000 - $25,000
per month
31 night min stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 9
31 night min stay
1 Review
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
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Recent Shelter Island Reviews

Beautiful home, perfect vacation

5 of 5
My wife and I were lucky enough to find this home and spend our July out there. Could not have been a more perfect stay. Home is meticulously designed and decorated, an open sunny home during the day and a warm retreat at night. The garden and pool is a perfect oasis and a great place to forget about day to day life and relax. Shelter Island itself is serene and has everything you could want from a summer vacation. Beaches and boating and barbecues or a short trip to the hamptons and the ocean. Hoping to make it back again next summer!
  • Submitted: Sep 9, 2014
  • Stayed: Jul 2014

Excellent vacation getaway

5 of 5
We had an amazing time in Greenport and love the Siren's Song Carriage House. It's perfectly located on a quiet side street but within walking distance to everything in Greenport. The carriage house is well maintained, comfortable, romantic and spacious. The fenced in back yard is perfect and really nice since we were traveling with our dog. The owner was flexible and was very friendly, even after arriving late at night over an hour late (yikes!). Thank you for making our vacation even better!
  • Submitted: Jul 29, 2014
  • Stayed: Jul 2014

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