Hi, I'm David!

My wife and I own these two beautiful beach homes on Shelter Island, they were originally build by an international travel writer. The 4+ bedroom home is styled after a European Home and the second house is very Len like smaller Carribean style Cottage. They sit on adjacent properties and for intents and purposes are completely self contained and separate. As an added benefit, there is a hidden gate that can be opened and the two properties connect and become one large compound.

The houses are OUR homes, they are NOT typical rental properties, we also live there and rent to help in paying for these two beautiful beach homes. Insides is decorated tastefully, it is NOT full of cheap furniture or worn out items. We pride ourselves in their style and upkeep, we only rent to couples and families and every year update both homes, even though they are only 8 years old. Last year we installed a beautiful new kitchen update with high end appliances and high solid surface counters. If you read the descriptions, you will see other updates we have made in the last few years. We also update the cottage every year with new furniture etc. A stay at our cottage was actually given away on the Valentines special CBS the Price is Right, chosen out of the thousands of properties out east.

Our homes have some of the highest ratings in the Hamptons and on Shelter Island and as you can see from the ratings, everyone that has stayed has loved it. Please feel free to ask any questions you like and we welcome you to our homes.

Here are my properties:

77' Wrap around porch 20' x 40' In Ground Pool
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Shelter Island Home
4 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

(10)“ Excellent ”10 Reviews

from

$400

/ night

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Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$400 - $795
Per week:$2,500 - $6,950
Pets allowed:Yes
Internet:Yes

DURING THE PEAK MONTHS, THIS HOUSE IS ONLY AVAILABLE BY THE WEEK OR LONGER! We just completed remodeling 2 of the baths and some additional painting. We just had custom plush white leather seating in the eat in kitchen nook as well as the window seat in one of the bedrooms....

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Perfection!

“ Excellent ”
June 9, 2015
This home was absolutely stunning. Photos don't do it any justice. It's grand in person. My girlfriends and I decided to take a mini getaway and we could not have chosen a better home. Super spacious, more than enough room for 8-10 people. Pool area was definitely our favorite place. We lounged out everyday, catching some great sun! The Sonos system Henry has in his home is out of this world ! We had music on all around the clock, it played outdoors by the pool and the patio which was a plus since it's so spacious, the sound was everywhere you wanted it to be. There's a speaker in every room and you can adjust it as needed. Truly a fantastic add to the home. Henry is great as well! He's connected remotely to everything in case something goes wrong. Definitely looking to come back int the fall for a family trip ! :)
Nora Khaled, Brooklyn

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Shelter Island New York Vacation Rentals - Cottage
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Shelter Island Cottage
2 Bedrooms / 1.5 Bathrooms / Sleeps 6
Cottage / 2 Bedrooms / Sleeps 6

(9)“ Excellent ”9 Reviews

from

$325

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:6
Type:Cottage
Per night:$325 - $495
Per week:$2,000 - $3,950
Pets allowed:Yes
Internet:Yes

With it's Caribbean flair, 3 waterfalls, 2 pools and 75' Koi pond, our Vacation home is possibly the most Romantic Hamptons Hideaway Vacation Cottage Home Rental ever. Located in the Estate Section of Shelter Island. Available weekly, monthly or for the entire season contact...

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Wonderful Surprise - a Mini Retreat

“ Excellent ”
July 25, 2010
After many years spent summering on Block Island, it was time for a change. The Shelter Island Hideaway cottage was better than we could have imagined. In an easy trip from CT, we were enticed by the farms and vineyards of the North Fork - reminiscent of Provence with farm stands and fields of lavender and sunflowers. Once on Shelter Island, it is easy to relax and forget about everyday concerns. Reddings and Greeny's Markets provide a wide variety of quality specialty foods to bring back to the cottage. Once there, it is difficult to find reason to leave, except to walk to the nearby beach at sunset. The open sun room flanked by two lap pools brings the outdoors in and the sound of the fountain flowing into the nearby Koi pond provides the perfect soundtrack. If the mood strikes to become social or to head out for a meal, there are good choices to meet most tastes on the island, with the South Fork a brief ferry ride away. Shelter Island Hideaway was the perfect respite for my two teenagers daughter and myself - relaxing and inspiring in a charming, zen-like setting.
Nina, Fairfield, CT

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David Josephson
David Josephson
From Manhattan, New York City
Member since March, 2008