->HAMPTONS - Shelter Island 4+Bdrm Euro Beach Home

77' Wrap around porch 20' x 40' In Ground PoolEvery Night at the Beach across streetBoat Launch and Beach Across streetVacation Rental, Pencil SketchNew Lower level 4th Bedroom75' Wrap Around Upper & Lower PorchFrench Doors to PorchThe Pool1 of 2 En-Suite Master Main FloorSide Entry to Vacation HomeMusic Room/Reading Room2 of 2 En-Suite Master Bedroom Middle LevelFall House EntranceWrap-a-round 75' PorchLiving Room Middle LevelGreat RoomDeck off of Master Bedroom 2nd FloorUpstairs Master BedroomEat in Kitchen Seats 6+Skylights Great RoomEn-Suite Pedestal Sinks Green Master BedroomCovered Wrap-a-round PorchFrom the Porch Looking in to Kitchen1 Acre Landscaped PropertyBoat Launch and BeachesSpring Bloom 4/26/08Enjoy this Sunset every night on the BeachGourmet Cruise & Capt. on32' Sport CruiserCabin of 32' boat looking aftCabin of 32' Cruiser looking forwardInside cockpit of Sport Cruiser Boat
“ Excellent ”
9 Reviews

From $400 / night



Bedrooms: 4
Bathrooms: 4
Sleeps: 10
Type: Home
Per night: $400 - $795
Per week: $2,500 - $6,950
Pets allowed: Yes
Internet: Yes
Description of the Shelter Island vacation home rental
New for 2011-2012 season. We have just installed Martha Stewart wall to wall carpeting on the entire upper level. The third week of August 2011 we replaced the just 8 year old kitchen with a beautiful new kitchen, including professional level stainless steel side by side refrigerator, a 5 burner convection gas range, new microwave and KitchenAide stainless inside and out dishwasher. The new countertops are solid surface high end SileStone. We now include a large screen new iMac for your use in the office with high speed ethernet and wireless thoughout the property, the computer is situated in the new office that resides on the homes 3rd level added in 2010.

In 2010 we completed a major undertaking that includes some very exciting and huge changes to our Hamptons Beach home. Shelter Island Hideaway beach house now includes a brand new 3rd level with 1100 square feet as well as another 500 square foot of covered outdoor space. This brings the home to over 3,000 square feet of indoor space and 4 1/2 Bedrooms, 3 levels and 4 full baths and over 1200 square feet of covered outdoor porch space.

The additions to Shelter Island Hideaway include a new bedroom, a 4th large luxury marble floored master bath, a large laundry room that include brand new high end Washer and Dryer. An Office/Study, and a 28' x 15' media room with wood floors, a huge Flat screen TV with 1500 Watts 5.1 Surround Sound complete the new additions. The new level also has 12' of French glass doors that lead out to a new (second) covered outside area with slate floors and finished walls and lighting, comfortably furnished. The addition includes over 1,000 sq. feet of interior space and 800 sq. feet of exterior covered porch/patio space.

The newly completed house now has 4 1/2 Bedrooms (2 Ensuite Masters), 2 with their own full bathrooms for a total of 4 full baths, There are also 4 oversized showers as well as 2 oversized heated Jacuzzi soaking baths. There is an additional small loft area off the 3rd floor bedroom with couch bed , it is perfect for a nanny or children.

32' luxury Cabin 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.

Located across street from waterfront, Our new Beach Vacation Home Rental is on the exclusive Shelter Island, "The Jewel of The Hampton's in the Estate Section. It's European Elegance and influence abounds in this custom Vacation Home rental.

Four Master Bedrooms plus Loft area sleeps 10 comfortably and more if needed. Two of the master bedrooms are En-Suite with twin pedestal sinks, Heated Jacuzzi tubs, and additional oversized showers.

Showcased on the 1+ Acre property is a beautiful in-ground 20'x40' Pool. Located just across from Spectacular Waterfront with 3/4 mile long Beach and Boat Launch.

Designed and built by the editor of International travel publication our spectacular 4 bedrooms, 4 bath plus loft home is perfect for entertaining and enjoying the pool, waterfront beach and splendid professionally kept mature landscaping.

The bedrooms are spread out over the 3 floors so no one is on top of anyone else. Three of the Bedrooms have vaulted ceilings 2 with skylights over the beds, imagine stargazing at night! Two of the bedrooms are designed in a Euro style and are en-suite with large jetted heated Jacuzzi tubs, twin pedestal sinks, huge tiled showers and separate pocket door with enclosed water closets.

The third huge bedroom is located upstairs with a separate bath. Enjoy the Island via Skylights above, a sliding 12' wood and glass doors leads to your private deck with water views, you can even hear the the sound of the water and waves lulling you to sleep. The expansive room includes a desk and work area for those type A personalities. Upstairs also includes a fabulous open music room/reading room with a couch bed that could be perfect for a nanny or children. There are more skylights and many windows, bathing the level and home with an abundance of natural light.

The lower level has the 4th bedroom and another full bath, just completed in April of 2010.

The main levels 35' soaring vaulted ceilings adds to the spacious feeling, the Great Room is very bright, showcased by natural light from the three skylights, myriad windows and multiple sets of Glass opening French doors. The French doors open from the Living room, Great room and Kitchen to the grand covered 70' L shaped wrap-around covered porch with multiple sitting areas, lounge couch dinning table, and teak cafe tables.

The porch contains a gazebo area with dining table and mood and rope lighting that overlooks both the beautiful landscaping and the stunning in-ground 20' x 40' pool. Bluestone, expansive lawns and beautiful mature landscaping surround the pool and the property. Most of the property is fenced in, with teak lounge chairs around the pool, an amazing hammock and hammock chair great for reading, snoozing or just relaxing.

The large 1+ Acre property with it's 2 fabulous porch areas offer over 1500 feet of covered outdoor space absolutely perfect for relaxing to cool ocean breezes, entertaining is divine, dining or swinging on the wicker porch swing. Crank up the Weber Gas BBQ or teh Weber Charcoal BBQ if you prefer, blend up a batch of Margaritas, turn up the music - perfect place for friends and family gathering and entertaining.

Across the street is the splendid 3/4 mile waterfront semi private beach. You can launch your boat or Jet Ski from the free boat launch there, gaze at the yachts of all sizes. If you prefer to just relax the privacy and quiet of the semi private beach allows you to just listen to the water without a million people around you. Lie on your blankets or beach lounge and relax to the left on the semi private protected beach.

Bikes may also available for your stay as well as just about everything you may need to get away and have the most memorable vacation of a lifetime/

Rental Cribs for infants and children now also available.

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 across 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
Nov 27 2014 Nov 29 2015 $700 $700 $3,000 - 3 Nights
Nov 30 2014 Dec 14 2015 $400 $525 $2,599 $7,500 3 Nights
Mar 29 2015 Apr 26 2015 $475 $615 $3,250 $8,900 3 Nights
Apr 25 2015 May 16 2015 $550 $650 $3,800 $9,500 3 Nights
May 16 2015 May 23 2015 - - $4,495 $13,500 1 Week
May 23 2015 May 30 2015 - - $5,750 $13,500 1 Week
May 30 2015 Jun 20 2015 - - $6,280 $21,000 1 Week
Jun 20 2015 Jun 27 2015 - - $6,395 $21,000 1 Week
Jun 27 2015 Jul 04 2015 - - $6,950 $22,900 1 Week
Jul 04 2015 Sep 12 2015 - - $6,950 $22,900 1 Week
Sep 10 2015 Sep 20 2015 $745 $795 $5,495 $15,950 4 Nights
Sep 19 2015 Oct 05 2015 $695 $795 $4,495 $13,500 3 Nights
Oct 05 2015 Oct 26 2015 $595 $695 $3,550 $75,000 3 Nights
Oct 26 2015 Nov 16 2015 $425 $525 $2,995 $7,500 2 Nights
Nov 16 2015 Nov 26 2015 $400 $525 $2,500 $7,500 3 Nights
Dec 14 2015 Dec 21 2015 $425 $530 $2,700 $7,500 3 Nights
Dec 21 2015 Jan 04 2016 $595 $695 $3,850 $8,000 5 Nights
Mar 08 2016 Mar 29 2016 $450 $595 $3,100 $7,500 3 Nights
View all periods
Check In: 3 p.m. Check Out: 10 a.m.
Deposits: Deposit required at time of reservation, amounts vary depending upon how much time in advance the reservation is made.
Payment Options: Cashier's Check, Money Order, Personal Check
Other Fees: We require only a DAMAGE/SECURITY DEPOSIT of $750, along with a small fee of $89 purchases a policy that covers you for the entire stay, there is no deductible . There is a utilities charge that covers pool servicing, Cable TV, gas and electric and a groundskeeper that is there 1-2 days a week. If accepted there is an additional required daily Pet Charge and additional security. $235 cleaning charge per stay, additional cleaning available and may be required for stays longer than 1 week.



  • Beds

  • 4 Queen Beds
  • 1 Sofa Bed
  • Features

  • Air Conditioning
  • Fireplace
  • Hot Tub
  • Pet Friendly
  • Balcony
  • Full Kitchen
  • Lanai
  • Porch
  • Beach Chairs
  • Hardwood Floors
  • Linens Provided
  • Private Pool
  • Beach Towels
  • Heating
  • Parking Included
  • View (Water)
  • Deck
  • High Speed Internet
  • Patio
  • Waterfront
  • Appliances

  • Alarm Clock
  • Dishwasher
  • Microwave
  • Stove
  • Blender
  • Gas Grill
  • Oven
  • TV (Cable/Satellite)
  • CD Player
  • Hair Dryer
  • Radio
  • Toaster
  • Charcoal Grill
  • Ice Maker
  • Refrigerator (Full)
  • VCR
  • Coffee Maker
  • Iron
  • Stereo
  • Washer/Dryer
  • DVD Player
  • Activities

  • Beach
  • Sailing
    (<1 mile)
  • Basketball Court
    (2 miles)
  • Movie Theater
    (4 miles)
  • Bicycling
  • Scuba Diving
    (<1 mile)
  • Gym/Fitness Center
    (2 miles)
  • Winery
    (4 miles)
  • Boating
  • Snorkeling
    (<1 mile)
  • Ice Skating
    (2 miles)
  • Bowling
    (5 miles)
  • Pool
  • 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 home rental in Shelter Island, New York

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



Wonderful Family Vacation

October 2, 2011

We stayed at this amazing house from Sep 10-17 and had the best time (we = two couples and two toddlers). The house was perfect. Great location with all the amenities you can imagine inside and outside the house (pool, large back yard, outdoors storage for bikes, grills, 4 bedrooms (one of them a loft), the best kitchen, nice entertainment room, etc. The house was also just 2 minutes away from a very nice beach, totally quiet, literally across the street. The owner was very easy to deal with and everything was done very professionally. We had a small issue with the fridge and called and he responded right away. Problem solved in 5 minutes. There were really no cons. Maybe the fact that you have to bring your own garbage to the local recycling dump but that was not a big deal because we knew about it from all the information that the owner gave us. We would love to come back next year.

Linda Phelan

Linda Phelan

newport center, vt

shelter island home

October 6, 2010

The house was a lovely surprise. It was a classic beachhouse, incredibly equipted and clean,and no musty smell that is typical. The "compound" has 3 houses, each with it's own personality. (We rented the red house.) It is a great place for a family reunion. We had 12 people eating dinner in the dining room and it was a delight! We would definately recommend this rental to anyone.

Ken Weber

Ken Weber

New York


July 19, 2010

My family and I could not ask for a better family vacation at this beautiful and inviting Shelter Island retreat. House is charming, warm and conveniently located to beach. Sunsets were amazing!!! If your looking for a beautiful, private quiet getaway can't go wrong here.



New York, NY

Wedding weekend in Shelter Island

October 22, 2009

What a great house! Had a friend's wedding to attend in Shelter Island and this was the perfect place to stay. Very clean and open. Outdoor porch was spacious and perfect for enjoying a few pre-wedding drinks with friends.

Deb O

Deb O

New York, NY

Perfect Getaway

September 29, 2008

The perfect antidote to city living. Whether it's beautiful weather so you can enjoy the pool or raining and you have the porch as well as fireplaces, this place is truly magical. The house is very comfortable and the cottage is so special. Each has its own special features. The house's kitchen is big enough for a big family to cook together-the hammock is crying "Nap!" and being a block and half away from the water to see the sunset makes it even more inviting. I would definitely recommend this to anyone who wants a beautiful, well-appointed, extremely clean and very private space. I work at Dwell and feel that design is very important. This fits the bill.

Jo Anne Schlesinger

Jo Anne Schlesinger

Manhattan, NY

The Perfect Beach House Experience

September 27, 2008

This is a special place. The main house is lovely -- open, airy, beautifully furnished, comfortable with one of those wide wrap-around porches that beckon you to sit, read, relax, chat. I ended up spending almost a whole day in this incredible spot. The grounds are also lovely -- the pool, the lawn and being one block from a quiet, almost private-feeling beach was incredible. The "cottage" is also an incredible place–a jewel in the crown. It's also an open, airy space with it's own entrance, pool(s) and rock stream. The property is truly a paradise and Shelter Island is really magical. Once you get on the ferry, you really feel that you're "away." I had a wonderful time here.

kathy nannizzi

kathy nannizzi

new york, ny

Lovely Paradise

September 19, 2008

We had such a great time here, and love, love, love this house. Shelter island is a great low-key vacation spot, and this house offers the perfect opportunity to take advantage of it. The pool is great, the hammock is true paradise, and the open nature of the house is great for groups. We had a blast and will recommend it to all of our friends.

Barbara Brown

Barbara Brown

Brooklyn, NY


August 19, 2008

every minute of my time at this beautiful home was enjoyable. the pool is heavenly, as are the grounds. cooking in the kitchen was a dream - everything you could possibly need for a gourmet meal or simple island brunch. Shelter Island is in my heart forever!

Dawn Doherty

Dawn Doherty

New Jersey

Pure Bliss

August 13, 2008

My first visit to Shelter Island was absolutely perfect. The home was spectacular- open, airy with a "wrap around" terrace that we practically lived on all week. Jumping in the refreshing pool between long bike rides, runs to Sunset beach, and shopping in Sag Harbor made the experience that much more enjoyable. If you have not been to Shelter Island before I highly recommend that you do so and this home was a great base for one of the most relaxing vacations I have taken in my life.

Owner Supplied Testimonials

The house is beautiful, the pool is great. Love the huge outdoor covered porch and the fact that the waterfront was across the street. Took kids back to the home for lunch everyday, or if they were in the sun too much.

Very close to everything on the Island, really enjoyed Shelter Island more that the Hamptons.

CR NYC Attorney

Had a fabulous time, the home is beautiful, the Island is wonderful, already booked for next year.

JK Solomon Brothers VP

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Page Views This month: 206 This year: 1,386 Since listed: 31,099
Last updated: April 16, 2015

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Owner Profile

David Josephson

David Josephson

(646) 833-8736

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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