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AIA AWARD WINNING COUNTRY ESTATE IN TRANQUIL SHELTER ISLAND

Photo gallery for AIA AWARD WINNING COUNTRY ESTATE IN TRANQUIL SHELTER ISLAND

A large, modern house with a prominent gable roof, large windows, and a covered patio area.
A covered patio area with a brick wall, wooden furniture, and a green column.
A covered patio with a wooden deck, a round table with chairs, and a sofa with pillows.
A spacious living room with a fireplace, two sofas, a coffee table, and decorative items like a lighthouse and sailboats.
A two-story house with a wooden exterior, a fenced yard, and a flagpole.

Reviews

10 out of 10
Exceptional

Highlights

  • Discover nearby landmarks

    Near Crescent Beach
4 bedrooms2+ bathroomsSleeps 9

Popular amenities

  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Washing machine
  • Internet
  • Onsite parking available

Explore the area

View map
Shelter Island, NY
  • Place, Crescent Beach
    ‪19 min walk‬
  • Place, Sunset Beach
    ‪2 min drive‬
  • Place, The Hamptons Beaches
    ‪15 min drive‬
  • Airport, East Hampton, NY (HTO)
    ‪32 min drive‬

Where you'll sleep

4 bedrooms (sleeps 9)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

Bedroom 4

3 Single Beds

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Bathtub · Toilet · Hair dryer

Bathroom 2

Towels provided · Bathtub or shower · Bathtub · Toilet

Bathroom 3

Towels provided · Toilet

About this property

AIA AWARD WINNING COUNTRY ESTATE IN TRANQUIL SHELTER ISLAND

Discover the beauty of Shelter Island from this Award winning, Architect owned and designed, 4-bedroom estate.

Whether you're lounging by the fireplace in the cozy clearstory living room or enjoying the fresh air on the spacious iconic wrap around porch, this property is perfect for a relaxing carefree summer getaway. The First floor encompasses an open floor plan seamlessly connecting kitchen, dining, living room and cozy den spaces as well as a private master suite. Second floor has 3 additional bedrooms and bathroom with access to an exterior observation deck perfect for bird watching with an early morning coffee. Guests will also have access and use of the first floor to the accessory 2 car garage structure on the property.

This Property is located within a prominent Hamptons style estate area of the Island and within walking distance to multiple beaches. Bicycles, kayaks and paddle boards can be rented on island if so desired. And don't forget to "take a hike" at the Mashomack Preserve, with over 2000 acres of interlacing tidal creeks, woodlands and freshwater marshes, it is not to be missed.

We hope you'll enjoy your stay at our estate.

Nearby Beaches:
Shell Beach, Crescent Beach (Sunset Beach), Crab Creek Beach, Bootleggers Alley Beach.

Nearby Grocery Stores:
IGA

Nearby Restaurants and Bars:
Dan Brock's Barbecue at Ellie's country store excellent sides and puddings in mason jars.

Marie Eiffel- in the Heights a wonderful great take-out food.

Ram's Head Inn- always special even just for cocktails on the beautiful lawn in Adirondack chairs.

Kyles- fantastic homemade jelly and cinnamon doughnuts croissants and cakes.

Commander Cody's- great fish store, and fabulous barbecue- pan fried chicken, and take out fish.

Vine Street Cafe- excellent food, five stars.

Maria's kitchen- great take out Mexican- great homemade chips and guac.

Shelter island slice for pizza.

Chequit- in town.

Salt

Leon 1909

Add dates for prices

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House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

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Children

Children allowed: ages 0–17

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Events

No events allowed

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Pets

No pets allowed

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Smoking

Smoking is not permitted

Important information

You need to know

Property # 4443625vb
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
On-site parties or group events are strictly prohibited
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

About the area

Shelter Island

Shelter Island is home to this holiday home. East End Seaport Maritime Museum and Railroad Museum of Long Island are cultural highlights, and some of the area's landmarks include Greenport Carousel and Camera Obscura. Shelter Island Whale's Tail and Bay Street Theatre are also worth visiting.
Map
Shelter Island, NY

What's nearby

  • Crescent Beach - 19 min walk - 1.6 km
  • Sunset Beach - 2 min drive - 1.8 km
  • The Hamptons Beaches - 15 min drive - 9.0 km
  • Wolffer Estates Vineyard - 32 min drive - 23.9 km
  • Cooper's Beach - 51 min drive - 41.5 km

Getting around

  • Greenport Station - 28 min drive
  • East Hampton, NY (HTO) - 48 min drive

Restaurants

  • ‪North Fork Roasting Co. - ‬32 min drive
  • ‪Pridwin Hotel - ‬12 min walk
  • ‪Sunset Beach Restaurant - ‬2 min drive
  • ‪Eddie’s - ‬28 min drive
  • ‪Nookies - ‬28 min drive

Frequently asked questions

Is AIA AWARD WINNING COUNTRY ESTATE IN TRANQUIL SHELTER ISLAND pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at AIA AWARD WINNING COUNTRY ESTATE IN TRANQUIL SHELTER ISLAND?

As of 18 September 2026, prices found for a 1-night stay for 2 adults at AIA AWARD WINNING COUNTRY ESTATE IN TRANQUIL SHELTER ISLAND on 19 September 2026 start from NZ$19,257, 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.

How much is parking at AIA AWARD WINNING COUNTRY ESTATE IN TRANQUIL SHELTER ISLAND?

On-site parking is available at the property.

What time is check-in at AIA AWARD WINNING COUNTRY ESTATE IN TRANQUIL SHELTER ISLAND?

Check-in begins at 4:00 PM.

What time is check-out at AIA AWARD WINNING COUNTRY ESTATE IN TRANQUIL SHELTER ISLAND?

Checkout is at 10:00 AM.

Where is AIA AWARD WINNING COUNTRY ESTATE IN TRANQUIL SHELTER ISLAND located?

Situated in Shelter Island, this holiday home is within 1 mile (2 km) of Crescent Beach and Sunset Beach. Shelter Island Country Club is 1.7 mi (2.7 km) away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 1 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic experience staying in Shelter Island: spacious and clean home; amazing location with beaches within walking distance and many restaurants close by. The outdoor space at the house was the standout; we really enjoyed the outdoor furniture, which including a spacious dining table and couches we used to relax and enjoy the Shelter Island sun and breeze!
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 14 nights in Oct 2025
Response from VrboOwner on 25 August 2026
Great guest! Left my place spotlessly clean!

About the host

Hosted by Jonny B.

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Languages:

English

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