>>> ROMANTIC Beach Getaway! Seclusion, Waterfalls

Open Air Room Overlooking Pond & Pools
Open Air Room Overlooking Pond & PoolsThe European Inspired Zen Like CottageInside Open air room - Doors ClosedBluestone Porch . Beamed with Glass overheadPond with Waterfalls Traverse the PropertyView of Pond and FountainsPond at Tea House CottageBluestone Area, Pond abutsOne of the many waterfallsSide view showing Dipping Pool & Covered outdoor aDipping Pool, More Sliding Doors Outside ShowerFood Bar overlooking Dipping Pool and PondDipping PoolLiving Room Seating areaKitchen Looking out toward 3 Sided Fireplace & OffOffice AreaMaster Bedroom Suite, 2nd LevelBath with Jetted and Heated Jacuzzi Tub. SkylightsCottage Through Gazeebo1 of the Roman 4' Deep Dipping Pool w/waterfall
“ Excellent ”
9 Reviews

From $340 / night



Bedrooms: 2
Bathrooms: 1.5
Sleeps: 6
Type: Cottage
Per night: $340 - $495
Per week: $2,195 - $3,950
Pets allowed: Yes
Internet: Yes
Description of the Shelter Island vacation cottage rental
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 us early for your desired dates.

Desire a peaceful, quiet secluded place to spend your vacation? Our 75' Koi Pond has a 6' Water-Fall, Open one of the 16 Glass French Doors and you can actually sit inside the house while dan gelling your feet in either of the 2 Roman Dipping Pools that abut the house. Located just across street from Waterfront, we have a spectacular semi-private Mile long Beach where you can swim, sun launch your Boat and take in the nightly spectacular sunsets.

Secluded, yet located just across the street is your own semi-private waterfront and beach, the sound and smells of water abound. Relax while you are surrounded by the myriad sounds of the relaxing water features including, 3 waterfalls, fountains, 2 pools the beach or our huge Koi Pond.

There is a waterfall in each of the 2 dipping pools which are abutted directly outside the 3 sided sun filled room. Almost the entire lower level has opening glass doors that create an amazing Zen-Like open-air room.

The Koi pond has a natural rock waterfall a large rushing waterfall. With Koi, Goldfish, a few frogs, occasional turtle and dozens f species of birds, it is like being in your own sanctuary!
Enjoy the outdoors with a private large outdoor shower area.

The Hamptons Shelter Island vacation hideaway is very secluded and was designed and built by an international travel editor to bestow the feeling and essence of being at a secluded Caribbean hideaway. There are 2 levels of blissful living, each with its own multisided gas fireplaces.

Ceramic tiles covers the floors extending outside the open-air room to the hand laid bluestone covered meditation/relaxation area. A full kitchen with dishwasher and glass breakfast area overlooks the pond and dipping pools and waterfalls.

Seeking peace? The Shelter Island Hideaway Beach Vacation Cottage is serenely peaceful - perfect for romance, writer or artists inspiration, inspiration, yoga and meditation, or simply complete relaxation. With it its peaceful outdoor space you will truly be transported. Sit back and enjoy, the large pond with frogs and dozens of species of birds transcends the entire property with rushing stone waterfall.

Sit, talk, listen to music, read or entertain in the living room. The first level is an open floor plan and encompasses the Kitchen, The Glass sliding door enclosed room with cathedral ceilings, the kitchen office and lovely bath.

The Eastern influenced landscaping with beach grasses, mature Russian olive trees and Bamboo add to the ambience. Step from the large open air room enclosed by 3 sides of French Glass window doors to the bluestone floor of the beamed and pergola covered outdoor space to dine or sit and relax, or even sit inside with your feet dangling in one of the two outdoor dipping pools flanking the space. A Royal Dutch Day Bed (sleeps two) sits in the middle of the cathedral ceiling room surrounded by sliding doors creating an "open air room," just inches from water. Bamboo shades close for privacy when desired.

An office area with ethernet and high speed wifi with hand painted Armoire, large glass desk, an iPod/iPhone stereo overlooks the grounds, pond and wading pool through the floor to ceiling wood and glass sliding door. There is a full sized washer and dryer hidden away in a closet.

Up the hand painted spiral staircase is the Master Bedroom Suite. There is a European styled elegant country cottage style area over the Queen bed with skylight above. A magnificent tiled 2-sided gas Fireplace separates the bedroom from the bath.

The bathroom includes the gas fireplace directly across from the large Jetted and heated Jacuzzi bathtub. Twin porcelain Pedestal Sinks are included in the generous bath.

This property is a one of a kind paradise, perfect for honeymooning couples, any one seeking romance, relaxation and sheer European or Caribbean Elegance.

Pet Policy. Please enquire
Area Information
'Un-Hampton' Hampton's is what you will experience while staying our Shelter Island Hideaway Vacation House rental on Shelter Island. Just 100 miles from Manhattan you can vacation as if you were in the French Riviera. Travel just a mile to the cosmopolitan Sunset Beach and Hotel. Sunset Beach's hipster credentials come courtesy of its owner, André Balazs, of Chateau Marmont and Standard Hotel fame. You can yacht and celebrity gaze here if you so desire or simply enjoy this Hamptons area NY area protected Island peaceful nature, surrounded by dozens of Coves and Bays, The Long Island Sound and preserves.

The Hamptons are the Hampton 's, today's playground of wealthy New Yorkers, a more retail oriented version of what the North Fork used to be in the days of Gatsby and before. Shelter Island is located between the forks of Long Island, is a different story, quaint, relatively uncharted territory.

From both Shelter Island NY Vacation homes you can walk to the Perlman Music Camp or to the gorgeous and famous Sunset Beach for the beat of today's Music, Celebrity watching, Yacht gazing and of course swimming, skiing, boating and picnicking. For Independence Day, July 4th Sunset Beach features a fabulous Fireworks display. Shelter Island allows for you to enjoy the quiet streets for biking, rollerblading and the dozens of gentle coves for kayaking and canoeing, fishing and boating... It really doesn't get any better than this!

Shelter Island is just a few minute ferry ride to both the exciting Hampton's, and Greenport. The South Fork has the Hamptons nightlife, while the North Fork has a bountiful selection of top Wineries, Orient Point and Water front bars, Pubs and Eateries; including fantastic Restaurants like the Zagats rated and Conde Naste Hot List restaurants, the Frisky Oyster.

Shelter Island is considered the jewel of the Hampton's. Lulled by the tides of its Peconic, Gardener's and Shelter Island Bays, this NY Vacation Island is an 8,000-acre paradise; Shelter Island offers pristine beaches, breathtaking water views, historic homes and gourmet eateries in a truly unique pristine upscale setting.

Our Vacation home allows you to enjoy the peaceful and quiet streets, Creeks and Bays for kayaking, canoeing, fishing and the Mashomack Park with its multitude trails and nature programs for both children and adults.

More than one-third of the island has been set aside as the Nature Conservancy's Mashomack Nature Preserve, a great destination for hiking and witnessing the island, it 's many species of wildlife and birds, just a as it originally was nearly 400 years ago.

From our Hamptons area Shelter Island Vacation Home rental it is just a short ferry ride to the south's Sag Harbor and East Hampton with its restaurants, Movie Theater and famous shops. The North ferry takes you to The North Fork and Greenport with its Tall Ships, famous Merry-Go-Round, boutique shops, and dozens of Wineries, restaurants and surrounding vineyards.

McArthur airport is just 50 miles west, and just bit further to Kennedy Airport, LaGuardia Airport, and Newark NJ airport. From most areas you can take the Hampton Jitney, or the Long Island railroad directly to Greenport and a $2 ferry ride to Shelter Island.

About the owner

Owner Profile

David Josephson

David Josephson

  • About:

    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...
  • View full profile


Availability Calendar



Begins Ends Week
Weekly Monthly Min
Mar 19 2016 May 07 2016 $340 $395 $2,395 $7,495 3 Nights
May 09 2016 May 27 2016 - - $3,195 $10,850 1 Week
May 27 2016 Jun 02 2018 - - $3,395 - 1 Week
Jun 04 2016 Jun 30 2016 - - $3,695 $12,500 1 Week
Jul 01 2016 Jul 09 2016 - - $3,950 - 1 Week
Jul 09 2016 Sep 03 2016 - - $3,896 $12,350 1 Month
Jul 25 2016 Sep 05 2016 - - $3,950 $12,350 1 Week
Sep 03 2016 Sep 17 2016 - - $2,895 - 1 Week
Sep 15 2016 Oct 03 2016 $435 $495 $2,250 $8,850 3 Nights
Sep 17 2016 Oct 31 2016 $435 $495 $2,195 $7,950 3 Nights
View all periods
Check In: 3 p.m. Check Out: 10 a.m.
Deposits: Please enquire, generally Saturday to Saturday during high season. 2 day minimum all other times
Payment Options: Cashier's Check, Money Order, Personal Check
Other Fees: We NO longer require a large DAMAGE/SECURITY DEPOSIT, instead, a small fee of $89 purchases & a refundable $750 security, policy covers you for the entire stay. The utilities charge $210 weekly covers a weekly pool cleaning servicing, Cable TV, gas and electric and a Groundskeeper that is there 1-2 days a week. If accepted there is an additional required Pet Charge. $235 cleaning charge per week, additional cleaning available and may be required for stays longer than 1 week.



  • Beds

  • 2 Queen Beds
  • 1 Sofa Bed
  • Features

  • Air Conditioning
  • Full Kitchen
  • Linens Provided
  • Pet Friendly
  • Beach Chairs
  • Heating
  • Outdoor Shower
  • Porch
  • Cook
  • High Speed Internet
  • Parking Included
  • Private Pool
  • Deck
  • Lanai
  • Patio
  • View (Water)
  • Fireplace
  • Appliances

  • Alarm Clock
  • Dishwasher
  • Oven
  • TV (Cable/Satellite)
  • Blender
  • Gas Grill
  • Refrigerator (Full)
  • Toaster
  • Charcoal Grill
  • Iron
  • Stereo
  • Washer/Dryer
  • Coffee Maker
  • Microwave
  • Stove
  • Activities

  • Bicycling
  • Sailing
    (<1 mile)
  • Basketball Court
    (2 miles)
  • Movie Theater
    (4 miles)
  • Boating
  • Scuba Diving
    (<1 mile)
  • Gym/Fitness Center
    (2 miles)
  • Winery
    (4 miles)
  • Pool
  • Snorkeling
    (<1 mile)
  • Ice Skating
    (2 miles)
  • Bowling
    (5 miles)
  • Beach
    (<1 mile)
  • Water Skiing
    (<1 mile)
  • Park
    (2 miles)
  • Horseback Riding
    (5 miles)
  • Canoeing
    (<1 mile)
  • Whale Watching
    (<1 mile)
  • Playground
    (2 miles)
  • Miniature Golf
    (5 miles)
  • Fishing
    (<1 mile)
  • Windsurfing
    (<1 mile)
  • Shopping Area
    (2 miles)
  • Deep Sea Fishing
    (8 miles)
  • Hiking
    (<1 mile)
  • Golf
    (1 mile)
  • Snowmobiling
    (2 miles)
  • Ocean
    (10 miles)
  • Jet Skiing
    (<1 mile)
  • Grocery Store
    (1 mile)
  • Tennis
    (2 miles)
  • Surfing
    (10 miles)
  • Kayaking
    (<1 mile)
  • Parasailing
    (1 mile)
  • Racquetball
    (3 miles)
  • Aquarium
    (25 miles)
  • Lake
    (<1 mile)
  • Restaurant
    (1 mile)

Other Vacation Rental Amenities
32' Luxury Sport Cruiser Boat and captain now available!

Our luxury home also has an exclusive addition for the upcoming season! Now your vacation can also include the availability of a 32' luxury Cabin Sport Cruiser boat and captain. You and your party can enjoy a gourmet cruise in the beautiful waterways, durations lasting from 3-6 hours are available. Please contact us for full details, pricing, availability of pictures.

Rental Cribs now available for infants and toddlers.

Shelter Island is a protected Island between the North and South Fork on the tip of Long Island. Located less that 100 miles from Manhattan. The Island is pristine and quiet, but a 5 minute Ferry ride brings you to all the excitement and continuos celeb watching and night life of the Hamptons. The North Ferry's $2 ride brings you to the North Fork, with dozens of top wineries, restaurants, boating and much more.

Reviews (9)

Reviews for this vacation cottage rental in Shelter Island, New York

Have you been a guest of this property? Write a review!
“ Excellent ”
9 reviews


Fairfield, CT

Wonderful Surprise - a Mini Retreat

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.

Stefanie Williamson

Stefanie Williamson

Carle Place, NY

Shelter Island Hideaway, Cottage

July 21, 2010

Wonderful cottage. It was an incredible vacation, the cottage was so secluded, the pond, pools, outdoor shower was incredible. The cottage was completely open, clean and completely accomodated my husband and 2 year old daughter. We cant wait to go back next year!




Shewlter Island Vacation Getaway, Amazing!

July 14, 2010

My wife and I had some of the best days of the summer on July 4th weekend staying in a great, cozy, comfortable, fun cottage. We relaxed by the twin pools that surrounded the sun room, and loved the beautiful beach right across the street. Definitely cant wait to come back there!! Thanks for everything David! See ya soon. Daniel Schonfeld

Ellen & Bob Marin

Ellen & Bob Marin

Westchester County, NY

Truly Romantic

August 2, 2009

While the upstairs could use some refurbishing, it is nevertheless a wonderful place for a couple in love.

Carol and Ron

Carol and Ron

Simsbury, CT

Wonderful hideaway!!

October 8, 2008

My husband and I recently visited for the weekend and absolutely loved the cottage! We so enjoyed exploring the area and can't wait to make another visit. Carol and Ron

Gerri  and Steve

Gerri and Steve

Eatons Neck, NY USA

Great getaway!

August 18, 2008

This was such a peaceful and tranquil setting for our vacation. Anyone wanting to get away from it all should come here. The pools, waterfall and beautiful wildlife make it unique and relaxing. We just left and miss it already! Gerri and Steve

Brenda Shockey

Brenda Shockey

Salt Lake City, Utah

Lovely retreat

August 4, 2008

We enjoyed a very relaxing week at this lovely cottage. It was clean and well-appointed with many lovely european style touches. The pools were refreshing and the ponds and grounds were very nicely maintained. The owner was very responsive to our needs. We will definitely return.

Diane Piegare

Diane Piegare

Glenmont, New York USA

"Your search for paradise has ended"

July 14, 2008

How wonderful to know that a luxurious accomodation in a truly natural setting still exists! The best of both worlds, the rejuvenation of a spa but not closed off from the outdoors, instead you are living among nature. Sounds, sights are so fulfilling . Walk to beach and returning for a dip in the pools. The covered patio was a pleasure, it was a way to enjoy the sound of the rain and still be outside and not worry when the sun would return. Even when you are indoors you are always enjoying a glorious view due to the mulitude of windows. The cleanliness was excellent throughout, top to bottom. A hot and cold running water outdoor private shower. Ahhh... or an upstairs bath/jacuzzi? That was my dilemma for the day.The lovely owners assisited us in any way possible to make our stay stress free. Books abound if you forget your own. The island itself continues the unhurried life style. We will return without a doubt. A+ Sincerely, Diane and Andrew Piegare Albany,New York

Katherine Stevens

Katherine Stevens


Just one word "AHHHHH"

April 21, 2008

Even nicer then described, this cottage was just so [peaceful and relaxing, just what I needed in my escape from the city (NYC). The sound of the waterfalls, the birds and being able to open up the wall of doors made you feel as f you were one with nature. Great place for romance and located across the street from the water was the best, there every day. Highly recommend this property

Owner Supplied Testimonials

From a past Guest of Shelter Island Hideaway:

"Beautiful", that is what I said when the day I arrived! The day I left I asked the the charming owners to "please reserve this week for me next year", I am definitely returning.

Having the waterfront across the street was the best, as was the open air feeling with the 2 dipping pools, waterfalls and the pond. The grounds and outdoor areas were beautiful and just lulled me into the most relaxed state ever.

The worst part, leaving and heading back to work!


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Page Views This month: 45 This year: 216 Since listed: 28,336
Last updated: January 19, 2016

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$340 / night


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Owner Profile

David Josephson

David Josephson

201 693-7773

More about the owner
  • About:

    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...
  • View full profile

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