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Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992
Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992

Beautiful Secluded Family Home on Shelter Island.

Bedrooms 4
Space 3,200 sq. ft.
Property type house
Minimum Stay 7 nights


About the property

House, 4 Bedrooms + TV Room, 3 Baths, (Sleeps 8)

This is a magical house. It is surrounded by woods and a pond. The only sounds you hear are the birds and other animals, the wind in the trees. It is a one minute walk to Dering Harbor where the sunsets are neon pink.

A TV room with a flat screen can be set up as a 5th bedroom. It is upstairs, a glass room that feels like a tree house. It can be used as an additional bedroom using a blow up bed from the closet.

This is a fully equipped family home perfect for people who want to truly unwind and feel nature.

The back of the house faces a saltwater pond/marsh that constantly changes with the tides and the moon.

A large deck out back is furnished with comfortable seating and lounge chairs are around the pool.

There is a over-sized outdoor shower that looks out into the trees.

Keywords: Private, Comfortable, Large but Cozy.

More Details

Kim Dempster
Member since: 2012
Speaks English
Response time:
Within 12 hours
Response rate:
Calendar last updated:
25 November, 2017

About Kim Dempster

I love Shelter Island and hope to retire here someday. I adore the nature and the easy going people it attracts. It is the safest place I have ever been which helps me to totally rest when I am here. I have been renovating the house room by room from the first day I bought it, each room has been created with love and personal care.

Kim Dempster purchased this house in 2003

What makes this house unique

The sky filled with stars. The silence at night. Walks on the beach. The sun rise and sun sets. The ease of life here....


Accommodation and facilities for this holiday house in Shelter Island in Southold Town

Property Type:
  • house
  • Self-catering
Floor Area:
  • 3200 sq. ft.
House Rules:
  • Check-in: Noon / Check-out: Noon
  • Max. occupancy: 8
  • Minimum Age Limit for Renters ...
  • pets considered ...
  • children welcome ...
  • non smoking only
Location Type:
  • Water View ...
  • Air Conditioning
  • Clothes Dryer
  • Fireplace
  • Hair Dryer
  • Heating
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking Off Street
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Wood Fireplace
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Ice Maker
  • Kitchen ...
  • Oven ...
  • Pantry Items
  • Refrigerator ...
  • Hob ...
  • Toaster ...
  • Dining ...
  • Dining Room
  • seating for 12 people
  • 3 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
  • 3
  • 4 Bedrooms, Sleeps 8
  • Bedroom 4 - 1 Large Double Bed
    Bedroom 3 - 2 Single Bed
    Bedroom 2 - 1 Large Double Bed
    Bedroom 1 - 1 Large Double Bed
  • Queen size Beds (3), Double Beds (0), Twin or Single Beds (2), Sleep Sofa or Futons (1) TV room has a full blow up bed.
  • DVD Player ...
  • Satellite / Cable
  • Stereo ...
  • Television ...
  • Balcony
  • Bicycles
  • Terrace
  • Barbecue
  • 2 bicycles
  • wheelchair inaccessible
Pool / Spa:
  • Private Pool
  • churches
  • cinemas
  • marina
  • restaurants
  • winery tours
Leisure Activities:
  • antique hunting
  • beachcombing
  • bird watching
  • Boating
  • horse riding
  • Miniature golf
  • paddle boating
  • Shelling
  • Shopping
  • sight seeing
  • walking
  • Wildlife Viewing
Local Services & Businesses:
  • ATM/bank
  • fitness centre
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • golf
  • hiking
  • Kayaking
  • sailing
  • bay fishing
  • swimming
  • tennis
There is a salt water pond in the back that changes from pond to marsh with the tides and the moon. It is salt water so we are mosquito free.


Exceptional! 5/5 -
(7 traveller reviews)

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Beautiful Secluded Family Home on Shelter Island.
average rating of 5.0 based on 7 reviews
New York

Beautiful and relaxing spot on Shelter Island

  • 5 of 5

Two families stayed for a week. Everything you could need. Great location. Very nice and relaxing pool. Much appreciated Kim's hospitality. Thank you!

  • Review Submitted: 29-Jul-2017
  • Date of Stay: July 2017
  • Source: VRBO, from HomeAway
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And Oasis Within an Oasis.

  • 5 of 5

I stay at Kim's place every year and look forward to it every year. Getting on a ferry to Shelter Island in itself allows me to leave the real world behind. And then I arrive at this tucked away, just off the water, beautifully converted barn and I am in heaven. It is lovely and SO comfortable and clean and country chic without being precious. You can put your feet up and sink into a huge sofa. There is light a plenty and a kitchen fit for a chef with room for friends and fans to gather around. And then there is the HUGE dining table for all to break bread together. Kim's place is her vision: a place that is comfortable and friendly for people to enjoy each others' company. But with plenty of nooks and crannies to have privacy and read (or write) that novel undisturbed. I also love diving in the pool, BBQing and taking a bike ride on this most beautiful part of the island. It is really a special place within a special place. My friends still talk about our week there.

  • Review Submitted: 10-Apr-2016
  • Date of Stay: July 2015
  • Source: VRBO, from HomeAway
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New York

Peaceful and comfortable

  • 5 of 5

I have stayed at Kim's home numerous times over the years, usually in the summer but also in the spring and fall. What I love most about the house is the surrounding nature. The huge dining room and the upstairs den are surrounded by three walls of windows looking out upon the pool and the marsh and woods beyond. Even when you are inside, you have the feeling of being outside - and that is exactly what I want when I get the chance to escape the city. There are big comfortable decks right off the kitchen (and the other main rooms as well) so I would frequently find myself outside in the morning with a cup of coffee, watching the birds feed and the sun and winds move across the marsh out back, as my friends slept as long as they wanted in the many private bedrooms in different parts of the house - all super quiet and peaceful. I couldn't recommend Kim and her house more highly. She is a gem - reflected in the home's furniture, art, books, and design.

  • Review Submitted: 09-Apr-2016
  • Date of Stay: September 2015
  • Source: VRBO, from HomeAway
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An stunning oasis

  • 5 of 5

My family (husband and 2 yo) and another family stayed at Kim's gorgeous and magical home and can't wait to return. It's decor is warm, authentic but chic and modern (and super clean). It had everything we needed to cook and entertain. Loved the pool- (my son loved the outdoor shower), the morning views of the wetlands and birds in the distance (most amazing breezes- never needed air-conditioning), proximity to beaches and farmer markets and mostly Kim. She's perfect hostess who made our stay comfortable and memorable. We cannot wait to come back.

  • Review Submitted: 09-Apr-2016
  • Date of Stay: March 2016
  • Source: VRBO, from HomeAway
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New York City

Peter Mostert

  • 5 of 5

Myself and a few friends recently stayed at Kim's house. The house was so comfy. The house is in a little secluded place overlooking a protected marsh. A great pool with a wonderful BBQ area on the back balcony with great seating in and outside the house - comfortable for a large group. You will lack for nothing from a well equipped kitchen to very comfortable beds and many diffrent areas to the house if you want some quiet time. All that was promised was supplied and an owner that was a pleasure to work with. Highly recommend!

  • Review Submitted: 08-Apr-2016
  • Date of Stay: April 2016
  • Source: VRBO, from HomeAway
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Romantic and relaxing

  • 5 of 5

I had the great good fortune of staying at Kim's house last summer. It's large, airy, rustic and homey. This is a quintessential summer house --relaxed, casual but sophisticated. The dining room is glassed in with a view of the marshes and woods. Totally private and quiet. But that big table is perfect for loud fun dinners with friends. There are so many bedrooms all of them clean and white and romantic! I wish I could come back every summer because this house is very special. Also, it's on it's own little street with only one other house.

  • Review Submitted: 08-Apr-2016
  • Date of Stay: May 2015
  • Source: VRBO, from HomeAway
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Nearest Beach
3 Miles
Wades Beach Shelter island
Car: recommended

Bicycles on property. Sailing, boating, beaches, beautiful walks, wildlife preserve, concerts. MoPed and Kayak rentals avail.


Prices & Availability

Prices for this holiday house in Shelter Island, New York

Rental Basis:
per property
Owner accepts payment in:
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Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly * Event Price
My Standard Rate
7 night minimum stay
for 7 nights

Additional pricing information

Cleaning fee £143.02
Refundable Damage Deposit £1,430.2
Tax Rate 3.0%

Families only/ no shares

Owner's Cancellation Policy

  • 50% refund for cancellations more than 30 days before check-in date.
  • 100% refund for cancellations more than 60 days before check-in date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.
Ask Owner a Question

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