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NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT

Photo gallery for NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT

Exterior
Property grounds
Living area
Pool
Miscellaneous

Reviews

10 out of 10
Exceptional
5 bedrooms5+ bathroomsSleeps 125730 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

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 Twin 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.
Our prices include all fees. No hidden fees.

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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

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
This property uses a grey water recycling system
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
Property Registration Number 2024-L-0018

We should mention

This property does not have elevators

About the neighborhood

Shelter Island

Located in Shelter Island, this vacation home is on the waterfront. Havens House and East End Seaport Maritime Museum are cultural highlights, and some of the area's attractions include Shelter Island Whale's Tail and Greenport Carousel. Traveling with kids? Consider Railroad Museum of Long Island and Norman E. Klipp Marine Park. Kayaking, water skiing, and windsurfing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
View more Vacation Homes in Shelter IslandOpens in a new window
Map
Shelter Island, NY

What's nearby

  • Menhadden Lane Beach - 3 min drive - 3.6 km
  • Gardiner's Bay Country Club - 5 min drive - 6.0 km
  • Shelter Island Whale's Tail - 6 min drive - 6.7 km
  • Sylvester Manor - 7 min drive - 7.4 km
  • Shelter Island Historical Society - 8 min drive - 8.4 km

Getting around

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

Restaurants

  • ‪Claudios Clam Bar - ‬30 min drive
  • ‪Vine Street Cafe - ‬9 min drive
  • ‪Sunset Beach Restaurant - ‬11 min drive
  • ‪Crazy Beans - ‬29 min drive
  • ‪Lucharitos - ‬30 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 Mar 28, 2026, prices found for a 1-night stay for 2 adults at NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT on Apr 30, 2026 start from $1,874, 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?

Onsite 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?

Check-out is at 11:00 AM.

Where is NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT located?

This family-friendly Shelter Island vacation 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 mi (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 5 out of 5 reviews
Rating 8 - Good. 0 out of 5 reviews
Rating 6 - Okay. 0 out of 5 reviews
Rating 4 - Poor. 0 out of 5 reviews
Rating 2 - Terrible. 0 out of 5 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Lucy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful House, Beautiful Spot

We had a great stay here with our adult children and grandchild. The house has a good lay-out, and is beautifully designed. The kitchen is very well equipped, with lots of counterspace and a large pantry. We used both sitting rooms; one has a large table for jigsaw puzzles. The pool and hot tub were so pretty, and we ate at a table there, or on the covered porch, every night. There is a large, clean outdoor shower. We hope to be back!
Stayed 14 nights in Jun 2025
Verified

10/10 Excellent

Devon W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful and Relaxing

My family and I stayed here in July. It was absolutely perfect. It is so peaceful and relaxing even with 8 adults and two babies under 1 and a 4 year old. The pool and hot tub were our favorite part with beautiful views of the bay. The house is also so stunning. We did lots of different activities as well. The communication was great and every question I had was answered! I highly recommend this property if you’re looking for something to do with the family. You can really make the trip whatever you want.
Stayed 5 nights in Jul 2024
Verified

10/10 Excellent

Laurie G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Even better than the pictures!

Can’t say enough about Serena’s house in the Ram Island section of Shelter Island! It was sooo beautifully decorated, perfect layout, everything we needed in the kitchen, loved that it was all on one floor, I could go on and on. We were 7 adults and 4 children ages 6 mo to 3 years, and somehow it was perfect for all of us. The kids loved to run around in the yard. We loved the amazing view of the water, and the comfort of the house. We had local chefs prepare two dinners for us, which was an amazing add on. Would definitely love to rent it again. Thanks Serena!
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Bob P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Magical stay

We had very prompt answers to any questions we had before our stay. We checked in with the property manager Kim and she was great. This home is amazing. The home was a perfect blend of amazing decorations and comfort. The bedroom and bathrooms were perfect in everyway. The porch had an amazing view which connected to the 4 star pool. My family had a great time. We felt blessed to spend time in this beautiful home. I would recommend this home for any group or family. You will not go wrong. The surrounding area is absolutely perfect. We felt like we didnt need to leave the house because we had everything we needed.
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Alexandra C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing retreat with something for everyone!

My family- of 3 generations was able to enjoy a wonderful relaxing vacation. The pool was beautiful- clean and warm, and with the boat launch and small beach across the street we were able to use that with ease. The house was clean, beautifully appointed with all the amenities you could need. The porch was great to relax and take in the waterfront view. Serena and her property manager were easy to get in contact with and communicated regularly. We had a wonderful stay and the trip went off without a hitch! Anyone would be lucky to stay here.
Stayed 7 nights in Aug 2021

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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