NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT

Photo gallery for NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT

A wooden cabin with a pool, surrounded by trees.
A spacious living room with a stone wall, white sofas, and a coffee table.
A two-story house with a stone chimney, a porch with black railings, and a well-maintained garden with various plants and flowers.
A modern house with a covered porch, large windows, and a stone chimney.
A cozy living room with a stone wall, a fireplace, a sofa, and a coffee table.

Reviews

10 out of 10
Exceptional

Highlights

  • Beach, waves and sand
    Guests enjoy the stunning beach views at this property.
  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
Sleeps 125 bedrooms8 beds

Popular amenities

  • Private pool
  • Hot tub on site
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View in a map
Shelter Island, NY
  • Place, Menhadden Lane Beach
    ‪4 min drive‬
  • Place, Gardiner's Bay Country Club
    ‪6 min drive‬
  • Place, Shelter Island Whale's Tail
    ‪7 min drive‬
  • Airport, Montauk, NY (MTP)
    ‪73 min drive‬

Rooms & beds

5 bedrooms (sleeps 12)

Guest Bedroom 1

1 Queen Bed

Guest Bedroom 2

1 King Bed

Guest Bedroom 3

1 Queen Bed

Guest Bedroom 4 - Bunkroom

4 Single Beds

Primary Bedroom

1 King Bed

5 bathrooms, 2 half bathrooms

Guest Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Guest Bathroom 2

Soap · Towels provided · Toilet · Shampoo · Hair dryer

Guest Bathroom 3

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Half Bath off the Wetroom (Pool changing room/Sauna room)

Soap · Towels provided · Toilet

Outdoor Shower

Soap · Towels provided · Shower only · Shampoo · Hair dryer

Powder Room

Soap · Towels provided · Toilet

Primary Bathroom

Towels provided · Bathtub or shower · Bathtub · Toilet · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden
Dining area

About this property

NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT

Take the singular Shelter Island drive over Ram Island’s renowned causeways to this meticulously renovated and expanded 1933 charming, waterview home of stone and cedar on the most sought after Big Ram Island block. 5 bedrooms, 6 bathrooms and large living spaces flow seamlessly with the outdoors, thanks to the expansive covered porches off the living room and large patio connecting the pool and hot tub with the kitchen and family room. Every detail was considered in the home in terms of beauty, function and experience. It’s owner, a veteran in the home decor industry, designed all fabrics and wallpapers and spec’ed every detail. The house sits on 1.4 acres of land, with a large lawn, wraparound porches to take in the views and space for everyone to enjoy, lounge, play or explore.

Bask in the sparkling sunshine on Coecles Harbor, take in the sunset from the two hanging porch-beds, or waterview-dine on the covered veranda. Swim in the heated pool, relax in the grotto-like hot tub or infrared sauna, or paddleboard, sail, fish or kayak just out your front door off the small beach that’s shared by the neighbors. Paddleboards stay parked here, and morning dips are mandatory in this idyllic spot. Off the beach, 37 Tuthill has a boat mooring, useable by renters. A short walk to the end of Tuthill Drive brings you to Reel Point, a sand peninsula lined with osprey nest platforms and blankets of seashells.

Coecles Harbor is a protected deep-water harbor that faces Mashomack Preserve, with over 2000 acres of interlacing tidal creeks, woodlands and freshwater marshes, easily accessible by paddleboard off our beach. The harbor is prized by sailors, swimmers and fishermen for its pristine, protected waters. The island enjoys a similar sense of peace and tranquility.

Perfect for everything from a relaxing couples getaway to a fun-filled family or friends gathering, this is fantastically special home designed for making cherished memories, in a magical corner of the world.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed: family gatherings and birthday parties
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property Registration Number 2024-L-0018
Property # 2408229vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings and birthday parties) are allowed on site. Maximum attendees: 30
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Shelter Island

Located in Shelter Island, this holiday home is on the waterfront. The area's natural beauty can be seen at The Hamptons Beaches and East Hampton Main Beach. Consider The Clubhouse Hamptons for a night out or Shelter Island Whale's Tail if you're travelling with kids. Discover the area's water adventures with kayaking, waterskiing and windsurfing nearby, or enjoy the great outdoors with cycling.
Map
Shelter Island, NY

What's nearby

  • Menhadden Lane Beach - 4 min drive - 3.6 km
  • Gardiner's Bay Country Club - 6 min drive - 6.4 km
  • Shelter Island Whale's Tail - 7 min drive - 7.4 km
  • Shelter Island Historical Society - 9 min drive - 8.8 km
  • Mashomack Preserve - 10 min drive - 10.2 km

Getting around

  • Greenport Station - 31 min drive
  • East Hampton, NY (HTO) - 47 min drive

Restaurants

  • ‪Claudio’s Waterfront - ‬30 min drive
  • ‪Lucharitos - ‬30 min drive
  • ‪Noah's - ‬29 min drive
  • ‪La Capricciosa - ‬29 min drive
  • ‪Billys By The Bay Tiki Bar - ‬33 min drive

Frequently asked questions

Does NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

How much does it cost to stay at NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT?

As of 21 Aug, 2026, prices found for a 1-night stay for 2 adults at NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT on 20 Nov, 2026 start from S$35,970, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT pet-friendly?

No, pets are not allowed at this property.

How much is parking at NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT?

On-site parking is available at the property.

What time is check-in at NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT?

Check-in begins at 4:00 PM.

What time is check-out at NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT?

Checkout is at 11:00 AM.

Where is NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT located?

This family-friendly Shelter Island holiday home is located on the waterfront, 1.7 mi (2.7 km) from Menhadden Lane Beach, and within 6 mi (10 km) of Shelter Island Whale's Tail and East End Seaport Maritime Museum. Greenport Carousel and Railroad Museum of Long Island are also within 6 miles (10 km).

About the host

Hosted by Serena Dugan

Host profile image
I co-founded the home decor brand Serena & Lily (serenaandlily.com) 20 years ago, and oversaw design for the brand as their CCO for 14 years. I now have my own textile collection under the name Serena Dugan Studio (Serena Dugan.com) and am a painter. This house was my ultimate form of creative expression, and I used all my own fabrics and wallpapers, aside from a few fabrics I’ve collected from far off places. I plan on using this house as a creative retreat, as well as a showcase for what I make. I live on the West Coast and want to share this beautiful spot when I am not able to use it with those who will appreciate it.

Why they chose this property

Shelter Island, and particularly Ram Island, is a magical spot, and this house is my most peaceful place. I envision years of memories being made here, and others sharing the beauty and peace of this spot with those who appreciate it as I do.

What makes this property unique

This house has been considered to the nines, both in terms of beauty, comfort and overall experience. Decorating a home that feels wonderful to be in includes all three. I have gone to great lengths to create something wonderful there on Shelter. It’s my happiest spot, and I know visitors will feel and appreciate this as well.

Languages:

English, French
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