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Book Online or call VRBO Booking Assistance: 888-829-7076
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Winner of Best of Citysearch- Beach/Pool, 4+ Bedroom Hamptons Vacation

Bedrooms 5
Space 3,000 sq. ft.
Property type house
Minimum Stay 3 - 7 nights


About the property

4 Bedrooms + Loft, 4 Full Baths, New Kitchen, Sleeps up to 10, 3 Levels, 3 Porch

The Property was voted as Winner of Best of Citysearch!.

Shelter Island Hideaway is amongst the best summer getaway Vacation destination. The most confusing part is deciding whether you treat yourself to a relaxing for a Week, Month or the entire season!

We have thought of most everything to assure your stay will be beyond comfortable and enjoyable, luxuriate in One of The Hamptons highest ranked vacation homes located on Bucolic and Beautiful Shelter Island. Shelter Island is often called 'The Jewel of The Hampton's, drive your car on to the Ferry, just 8 minutes from The North Fork, or 3 minutes from Sag Harbor, on the South Fork of Long Island.

Our three story Beach Vacation Home Rental is located just across the street from a ½ mile stretch of a semi-private beach. Located in the exclusive Shelter Island Estate Section, privacy abounds.

Your private estate Vacation home has 3,000'+ square feet of indoor space. Light and bright with multiple Skylights and Walls of French Glass doors means you're bathed in open, bright indoor space. But, that's not all, open the French doors on either of the two levels and walk right to covered wrap around porch overlooking the huge pool. The center level has a wrap large wrap-around porch where you can dine read, relax on the oversized Papasan chairs, lounge on the new high-end outdoor sectional sofa.

The lower level has its outdoor sitting area; kids love the space as they have their own sectional and some privacy, right outside of the opening French doors. Direct access to the pool from either outdoor space via a couple of stairs.

The Upper floor has it;s own Juliet balcony right off the bedroom, just open the French doors and enjoy the fresh Shelter Island breezes and views of the water and treed areas. With a combined outdoor porch space exceeding 1,500 square feet, the days biggest decision may be where to relax.

Your beautiful vacation home was designed and built in 2007 by Editor of International travel publication, each of the four distinct oversized bedrooms can be considered "Masters." There are two very large bedrooms on the center level with vaulted 20'+ ceilings and designed in a European fashion and are En-suite, & the privacy of water closet. The upper level has another very large bedroom with an attached reading room/music room area with a sleeper couch as an optional sleeping area. The lower level has a new large bedroom as well.

There are four full fabulous baths, 2 of which include both a shower and amazing Oversize heated Jacuzzi soaking tubs, Tubs. The lower level bathroom is brand new, comprised of marble flooring, two windows, twin glass and wood vanities each with a vessel sink. The shower is an oversized shower with glass tile and glass doors. The upper bathroom has a single pedestal sink, commode and tiled shower with a skylight above. Just beyond the beach is a closed glass door laundry room with new high-end LG Oversized Washer, Dryer and sink.

Your vacation home is the perfect place for getting away from the city craziness, designed to allow for both profound relaxations as well as entertaining. Like to swim, just steps from the first two levels is a private, fenced in landscaped property with the 20x40 pool where there is a second dining table as well as multiple teak lounge chairs. Also and a short stroll across to the waterfront where you will find your semi-private beach, more than a ½ mile long. This semi-private beach is perfect for watersports of all kinds as well swimming and snorkeling, or just relax and work on your tan. The beach faces West, so every clear night you'll enjoy spectacular Shelter Island sunsets, be sure to bring your camera. Pack a picnic or bring any of your favorites Martini, Wine, Beer or Margaritas (plastics of every variety available at the house for your use). Prefer a "Town Beach"? 1 mile down the road is Sunset Beach, also know as Crescent Beach. There are lifeguards there, a restaurant and yachts up 300' Barry Diller's come from all around the Hamptons.

The new media room is quite large, measuring 28 feet by 15 feet. Two couches and lots of floor pillows for watching movies on the 70' High Definition LED flat screen TV, films and excellent with the hidden Kevlar end in-ceiling speakers, subwoofer, Blu-Ray and DVD Players are driven by a 1500 watt of 5.1 Sound system. From here, you again have access to the wonderful outdoors of Shelter Island, just open the 12' of French doors.

Just off the media room, even though this is your vacation. You'll find you may need to to do a little work; there is an office area with Wi-Fi as well as hard-wired Ethernet high-speed Internet access and a desk with a daylight lamp and comfortable rolling chair.

The new first-floor level also includes 12' of French glass doors that lead out to the second covered outside area with slate floors and finished walls and lighting, comfortably furnished for your to lounge, grab a bike or a pool toy.

We are constantly upgrading the Shelter Island Hideaway Vacation Home! Last year we bought a new Media room TV, going from 55' to 70'. We recently installed Martha Stewart wall-to-wall carpeting on the entire upper level. The kitchen though just ten years old was completely remodeled and updated, with all professional stainless steel side by side refrigerator, a five burner Professional convection gas range with warming drawer, new Professional Series Microwave Convection and a super quite Kitchen Aide stainless inside and out the dishwasher. For easy cleanup and beauty, you're sure to enjoy the solid surface high-end Silestone countertops and the glass tile backsplash.

Shelter Island Hideaway will provide you with that much-needed vacation to remember. Spend your time relaxed, enjoying the company of friends and family, watching and listening to the dozens of species of birds, smiling as the the bunnies hop by, the sunset views of passing deer and take in the natural professionally landscaped and maintained property and grounds. No need to do anything, allow Mariano, our Grounds person, to take care of the property on the weekend, the pool company to come in and professionally service and clean the pool every week. We have set up a system so if you require an additional cleaning while at home, you can easily arrange one (payment is your responsibility).

Everything you need is here at Shelter Island Hideaway Your vacation home is equipped with 2, BBQ's, if you prefer charcoal, there is a Weber grill for your use, or if you prefer gas, just fire up the Gas Weber grill. Weprovidehave a few loaner bicycles on the premise, there are pool floats and more, remember, this is your time to relax, so just do it!

New Feature: Dreaming of getting out on the water? Our 30' Cruiser may be available for fishing, sightseeing, cruising around the Island or Hamptons or even Charter Gourmet Cruise. Just ask, and we will do our best to accommodate your needs.

The Hampton's Shelter Island Description: 'Un-Hampton' Hampton's are 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 Shelter Island Hamptons Home you can walk to the Perlman Music Camp.

More Details

David Josephson
Member since: 2008
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
July 18, 2017

About David Josephson

The owner of two beautiful house on Shelter Island the Hamptons, our homes are NOT your typical rental homes and are decorated and furnished as "our homes'".

I am the CEO of an Online Marketing and Web Development company on Wall Street, Manhattan NY.

David Josephson purchased this house in 2008

Why David Josephson chose Shelter Island

Fell in love with the beauty of the property, the proximity to the water and Shelter Island, had to have it!

What makes this house unique

Highly rated, everything you need, close to everything. Winner of Best of Citysearch!


Silver Beach House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 3000 sq. ft.
House Rules:
  • Check-in: 4:00 PM / Check-out: 11:00 AM
  • Max. occupancy: 10
  • Minimum Age Limit for Renters ...
  • pets considered ...
  • children welcome
  • non smoking only
Location Type:
  • Beach ...
  • Beachfront ...
  • Near The Ocean ...
  • Resort ...
  • Town ...
  • Waterfront ...
  • Waterfront ...
  • Away From It All
  • Family
  • Romantic
  • Tourist Attractions
  • Activities Guide
  • Air Conditioning ...
  • Alarm Clock
  • Basic Soaps
  • Clothes Dryer ...
  • Filtered Water
  • Fireplace ...
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Laundry Soap
  • Linens Provided ...
  • Living Room ...
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Parking ...
  • Parking Off Street ...
  • Parking On Street
  • Sofa Bed
  • Telescope
  • Toilet Paper
  • Towels Provided ...
  • Washing Machine ...
  • Water Cooler
  • Wireless Internet ...
  • Blender
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Freezer ...
  • Grill
  • Kitchen ...
  • Lobster Pot
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Stove
  • Toaster ...
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 4 Bathrooms
  • Blue Room En-Suite Master Bath - toilet , shower , jetted tub , European Elegance
    Green Room En-Suite Master Bath - toilet , shower , jetted tub , European Elegance
    Upstairs Bath - toilet , shower , European Elegance
    Lower Level Marble and Glass Tile Bath - toilet , shower , Twin Sinks Contemporary Designer Bath
  • The Blue Room En-Suite Master Bath and the Green Room En-Suite Master Bath each include a heated jetted Soaker Jacuzzi tubs, separate Italian Tiled oversized Showers, twin pedestal porcelain sinks and a separate water closet contained with pocket doors. The House 3rd Master Bedroom Suite has a bath with Italian Tiled shower. The new 3rd Level has a beautiful designer series bath with Marble tiled floor, Glass Tiled oversized shower, 2 beautiful vessel sinks.
  • 5 Bedrooms, Sleeps 10
  • The Blue Room En-Suite - 1 queen , Large Master 14 windows. Heated Large Jacuzzi Tub & Shower
    The Green Room En-Suite - 1 queen , Large Master Skylight. Heated Large Jacuzzi Tub & Shower
    Bedroom 3 - 1 queen , 1 sleep sofa /futon , On Lower level, Access to Huge Marble Bath + Air Mattress av
    Convertible Bonus Room Open - 1 double , Not private our loft room is perfect for Kids/Nanny
    bedroom 4. Upstairs Huge Bedroom - 1 queen , Huge Master Suite with private Bath, Deck, open to below
  • The home is comprised of 4 Master Bedroom suites. Two of Bedrooms have vaulted ceiling with skylights over the beds, imagine stargazing at night! These are designed in a Euro style and are en-suite with large jetted heated Jacuzzi tubs, twin pedestal sinks, huge tiled showers & separate pocket door with enclosed water closets. The third huge bedroom is located up al stair with a separate bath. Skylights above, a sliding wood and glass door leads to your private deck with water views & the sound of waves. The expansive room includes a desk and work area Upstairs also includes a fabulous open music room/reading room with a couch bed. New for 2010 a completely new level of 1000' sq. Includes a Bedroom, Media Room, Marble and Glass Tile Bathroom, Laundry room, study and 600' of covered outdoor space. Need more space? A second private home on adjacent property available, Can become compound by opening secret locked gate in tall fence between properties, see listing #3513499.
  • Books ...
  • CD Player
  • DVD Player ...
  • Games ...
  • Music Library ...
  • Radio
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Toys ...
  • VCR
  • Video Games ...
  • Video Library ...
  • Balcony ...
  • Barbecue
  • Beach Towels
  • Bicycles ...
  • Boat ...
  • Deck / Patio ...
  • Golf ...
  • Kayak / Canoe ...
  • Lawn / Garden ...
  • Motorboat
  • Outdoor Grill ...
  • Outdoor Grill Gas
  • Patio
  • Porch / Veranda
  • Raft
  • Small Cooler
  • Tennis ...
  • Terrace
  • Unscreened Porch / Veranda
  • Walkway to Water
  • Wood Deck
  • 1 bicycles
  • 8 garden chairs
  • Long-term Renters Welcome
  • Low Allergen Environment
  • suitable for elderly or infirm
  • wheelchair inaccessible ...
Pool / Spa:
  • Heated Pool
  • Hot Tub ...
  • Jacuzzi
  • Outdoor Pool
  • Private Pool ...
  • Spa Whirlpool
  • Whirlpool
  • Whirlpool
  • autumn foliage
  • bay/sound
  • churches
  • cinemas
  • festivals
  • forests
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
  • synagogues
  • water parks
  • waterfalls
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • horseback riding
  • outlet shopping
  • paddle boating
  • photography
  • scenic drives
  • sight seeing
  • sledding
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • hiking
  • ice skating
  • jet skiing
  • mountain biking
  • paragliding
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • skiing
  • snorkeling
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
Highly rated, Winner of Best of Citysearch! this is not your 'typical' rental house. This is our home that we also rent. Furniture, amenities, art all first class. House is maintained weekly by a grounds person. The property is landscaped and manicured weekly. The 20x40 inground pool is cleaned weekly. The Semi-Private mile long beach is great for any wanter activities, super clean water for swimming, fishing, snorkeling and more. Picnic here, watch the among nightly sunsets.


Exceptional! 5/5 -
(9 traveler reviews)

Winner of Best of Citysearch- Beach/Pool, 4+ Bedroom Hamptons Vacation
average rating of 5.0 based on 9 reviews

Beautiful, Peaceful, Comfortable everything A++

  • 5 of 5

This house was the best rental property myself and famil have stayed. We have been renting vacation homes for a family, first six growing now to 10 for over a decade. For the most part, rental homes are, well rental homes. Beds not great, standard appliances, etc. Not Shelter Island Hideaway. The house was tastefully decorated, very comfortable furniture, great art.

The media room was like going to the movies, I have never seen a TV that big and the kids loved the movie like sound. The bedroom sizes were amongst the largest we have seen, not just one big master, but all, but all. Large bathrooms, most with two sinks and oh, those huge jacuzzi tubs, dreamy. The property is beautifully landscaped, the caretaker Mariano was very sweet and helped us out with a few request, Pool was pristine, the fenced in the backyard had lovely landscaping that was completely private. Not sure if our kids and grandkids loved the pool more or the beach across the street. They had two types of Weber BBQ's; my husband liked the charcoal, me, the gas was easy, just turn a button and it was on.

We will likely return this year, just putting our plans together now.

  • Submitted: Mar 29, 2017
  • Stayed: Sep 2016
  • Source: HomeAway
Owner's Response: Good afternoon. Wow, that was so nice of you right write all those wonderful things about your stay. Look forward to seeing you again later this year. Have a great Spring. David
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0 0

Beautiful house, not a typical rental

  • 5 of 5

My wife myself and my family thoroughly enjoyed staying in this house. Everything was so very comfortable we all have her own space. The media room was awesome but the kids loved it and we love watching movies.

Definitely returning in the summer so we can enjoy the pool and the beach. Thank you for your hospitality.

  • Submitted: Apr 23, 2017
  • Stayed: Apr 2017
  • Source: HomeAway
Owner's Response: Thank You Hope to see you again
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0 0

Best Service Provider !!

  • 5 of 5

Shelter Island Hideaway offers luxurious accommodation in a truly natural setting. It clean, serene, comes with a Jacuzzi, pool, and private beach across the road. It’s a true piece of paradise for any discerning vacationer.

  • Submitted: Apr 10, 2015
  • Stayed: Feb 2015
  • Source: HomeAway
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1 0


  • 5 of 5

Don’t let your dream of renting a vacation home take you any further than Shelter Island Hideaway. That’s where we found our dream vacation rental professionally landscaped with trees and facilities on par with 5 star resorts.

  • Submitted: Apr 6, 2015
  • Stayed: Dec 2014
  • Source: HomeAway
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0 0


  • 5 of 5

When it comes to Shelter Island Hideaway seeing or rather experiencing is believing. There are no words that can describe how exotic and charming the Hamptons is with a wonderful vacation home to enjoy every moment.

  • Submitted: Apr 1, 2015
  • Stayed: Jan 2015
  • Source: HomeAway
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0 0

What a Beautiful House, Property and Beach

  • 5 of 5

We were looking for a modern house near the water that would accommodate our family of 8. After days of searching we came across Shelter Island Hideaway. The pictures were amazing, but we wanted to make sure before booking our stay. We called the owner, David, he was extremely accommodating, even drove out form NYC to meet my husband and I at the house.Needless to say, we quickly fell in love with the property and the house.

The pool, perfect, just steps from the 2 huge outdoor areas so we could keep an eyer on the kids at all times. The yard, beautifully landscaped with flowers and trees and completely enclosed also gave us peace of mind knowing the kids could go no where without our knowledge. Speaking of the property, we (and especially the kids) just loved the groundskeeper, Mariano helped us with a few things and he kept the property and house immaculate.

The beach was lovely, most spectacular sunsets every night, easy to get to in just minutes and very few people. We also visited Sunset Beach, it was great with the restaurant and bar there and we got to see so many huge boats and even few TV celebs we recognized. The Island is lovely, the restaurants great and a quick ferry ride and we drove over to Mantauk for those huge waves.

We were intrigued by the boat that they have, my husband went once with the boys for fishing, and then I went with the girls for a cruse around the Hamptons.

We have already booked our next week and have friends that have booked time at the cute cottage next door too, how fun!

Love, love love this place and highly recommend Shelter Island Hideaway!

  • Submitted: Feb 6, 2012
  • Stayed: Aug 2011
  • Source: HomeAway
Owner's Response: Thank you for the kind words, we are so happy you guys had a great time. We look forward to seeing you this summer and spending a little time with you out on the boat. David and Helane
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3 1


Nearest Airport
50 Miles
Islip and all NY area airports
Nearest Barpub
3 Miles
The Dory
Nearest Ferry
2 Miles
North Ferry or South Ferry
Nearest Golf
2 Miles
Public Course
Nearest Train
2 Miles
LIRR Greenport also Hampton Jitney
Nearest Motorway
2 Miles
LIE, Route 25 or Route 114
Nearest Restaurant
3 Miles
Vine Street Cafe
Nearest Ski
0.1 Miles
Water skiing
Nearest Beach
0.1 Miles
Semi Private, across street. Many more on Island
Car: not necessary

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

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

Other Activities: Boating, Swimming, Jet Ski, Fishing, Beaches, Relaxing, Celeb watching, Hampton's

Golf: Gardiners Bay Country Club

Gardiners Bay Country Club is an 18-hole regulation length golf course in Shelter Island Heights, New York. This short layout has 3 sets of teeboxes for a fun, but challenging golfing experience. Online tee times may be available at Gardiners Bay Country Club or at nearby golf courses, usually offered at a discount from the normal rate.

Tees Par Yardage Course Rating Slope

Back 70 6359 69.3 121

18 total holes at facility

Green fees - $65 (approximate)

Designed by Seth Raynor and (R) William F. Mitchell

Built in 1896

Driving Range: Yes

Private golf course

Golf Pro: Robert J. DeStefano Course Superintendent: Mark S. Lester Manager: Kathy Regan

Ski: Water skiing abounds, no close snow skiing


Rates & Availability

Silver Beach House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
Summer 2
Jul 9 2017 - Sep 8 2017
Changeover Day: Saturday
7 night minimum stay
Late Summer
Sep 9 2017 - Sep 22 2017
Changeover Day: Saturday
7 night minimum stay
Leaf Peeping
Sep 23 2017 - Oct 28 2017
3 night minimum stay
Spring 2018
Apr 1 2018 - Apr 20 2018
7 night minimum stay
Late Spring 2018
Apr 21 2018 - May 11 2018
7 night minimum stay
Early Summer
May 12 2018 - May 24 2018
7 night minimum stay
Memorial day week 2018
May 25 2018 - Jun 1 2018
7 night minimum stay
Summer 1, 2018
Jun 2 2018 - Jun 22 2018
7 night minimum stay
Summer 2, 2018
Jun 23 2018 - Jun 29 2018
7 night minimum stay
July 4, 2018
Jun 30 2018 - Jul 7 2018
7 night minimum stay
Summer High Season, 2018
Jul 8 2018 - Sep 8 2018
7 night minimum stay
My Standard Rate
3 night minimum stay

Additional information about rental rates

Cleaning, end of stay $245
Utilities Per week Pool $245
Opt Renters Ins. $99
Pet Fee if OK'd $40pd $0
Refundable damage deposit $750
Property Damage Protection $99
Tax Rate 3.0%

The above rates are for JUST the 4+ Bedroom house. The Cottage is separate, but can be combined
The 4+ Bedroom House is Available all year!

Please contact us for Availability for either property, these 2 separate homes can be to form a compound compound or separately as individual houses separate adjacent properties.

Please Inquire for rate information on dates not above.

Cancellation less than 60 days prior till stay, 100% of deposit is forfeited. 60-120 days, 50% of deposit forfeited. 120 days or longer $400 paperwork fee will be incurred.

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
Contact Owner

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