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This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!

Photo gallery for This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!

Exterior
15 Westmoreland Drive... the front of the home
view from the water's edge
Property grounds
the boat dock

Reviews

10 out of 10
Exceptional
7 bedrooms6+ bathroomsSleeps 166500 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Rooms & beds

7 bedrooms (sleeps 16)

2nd floor - 2nd master

1 Queen Bed

2nd floor middle - the yellow room

1 Twin Bed and 1 Double Futon

2nd floor - the blue room

1 Queen Bed

5th bedroom

2 Twin Beds

Bedroom 6

1 Queen Bed

Bedroom 7 - walkout basement rec room

4 Twin Beds

first floor master

1 King Bed

6 bathrooms, 1 half bathroom

2nd floor - 2nd master

Bathtub · Toilet · Shower only · Jetted bathtub

2nd floor middle - the yellow room

Bathtub or shower · Toilet

2nd floor - the blue room

Bathtub · Toilet · Shower only · Jetted bathtub

Bathroom 5 - shared

Bathtub · Toilet · Shower only · Jetted bathtub

Bathroom 6 - walkout basement rec area

Bathtub or shower · Toilet

frist floor master

+1
Bathtub · Bidet · Toilet · Shower only · Jetted bathtub

Two 1/2 bathrooms on 1st floor

Toilet

Spaces

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

About this property

This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!

This luxury home includes 6 bedrooms with additional sleeping accomodations for 4 in the downstairs walkout recreational room. All bedrooms have ensuite baths, 300 count linens & mutiple pillows & plush towels. The gourmet kitchen is a cook's dream. With water views from all areas of the home, this house lends itself to outdoor dining as well as warm summer nights seated around the large outdoor fireplace pit... the ideal location for entertaining family and friends. For 2015, a beautiful in-ground heated gunite pool has been constructed with water views from the in-pool benches.
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 12:00 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

No events allowed
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Pets

Pets allowed: dogs and cats (limit 2 total)
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Smoking

Smoking is not permitted
CANCELLATION POLICY: 50% non-refundable on booking; 50% due 60 days prior, then no refund either

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
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

We should mention

A car is recommended for transportation to and from this property

About the neighborhood

Shelter Island

Located on the waterfront, this vacation home is in Silver Beach, a neighborhood in Shelter Island. Shelter Island Whale's Tail and East End Seaport Maritime Museum are local attractions and those in the mood for shopping can visit Greenport Farmers' Market and Love Lane. Traveling with kids? Consider Greenport Carousel and Railroad Museum of Long Island. Be sure to check out the area's animals with activities such as game walks and birdwatching.
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Map
Shelter Island, NY

What's nearby

  • Shelter Island Historical Society - 2 min drive - 2.5 km
  • Havens House - 2 min drive - 2.5 km
  • Sylvester Manor - 3 min drive - 2.9 km
  • Crescent Beach - 3 min drive - 3.6 km
  • Sunset Beach - 4 min drive - 4.3 km

Getting around

  • Greenport Station - 27 min drive
  • East Hampton, NY (HTO) - 50 min drive

Restaurants

  • ‪Vine Street Cafe - ‬8 min drive
  • ‪Sunset Beach Restaurant - ‬4 min drive
  • ‪Waypoint - ‬32 min drive
  • ‪Opties & Dinghies - ‬6 min drive
  • ‪Pridwin Hotel - ‬4 min drive

Frequently asked questions

Does This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental! have a pool?

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

How much does it cost to stay at This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!?

As of Mar 28, 2026, prices found for a 1-night stay for 2 adults at This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental! on Jul 1, 2026 start from $2,490, 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 This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental! pet-friendly?

Yes, this property allows cats and dogs (limit 2 total).

How much is parking?

Onsite parking is available at the property.

What time is check-in at This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!?

Check-in begins at 12:00 PM.

What time is check-out at This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!?

Check-out is at 11:00 AM.

Where is This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental! located?

This family-friendly Shelter Island vacation home is located on the waterfront, within 3 mi (5 km) of Crescent Beach, Sunset Beach and Shelter Island Country Club. Shell Beach and Sylvester Manor are also within 3 mi (5 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. 4 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

leah r.

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

Perfect house on the water

Our family had a great time. Gorgeous house and grounds, including dock. We already miss our morning coffees watching kayakers float by. Andrea was incredibly accessible and helpful.
Stayed 7 nights in Aug 2019
Verified

10/10 Excellent

Joseph S.

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

Summer vacation

My family and I had an amazing vacation at this stunning property. I am ready to book the same place for next year.
Stayed 8 nights in Aug 2019
Archival

10/10 Excellent

Jim M.

Gorgeous place! Every amenable for the perfect family vacation

This is a wonderful serene property right on the water. The rooms are fantastic with private baths in each room, ceiling fans and wonderful view from each room. The kitchen is fit for a gourmet cook and is open with plenty of seating, perfect for entertaining. There are multiple porches, sun room and sitting areas and the downstairs is perfect for families with teens. I'd highly recommend this property for a family gathering, reunion, wedding or any significant special event. I plan on visiting again!
Archival

10/10 Excellent

Guest

This is the dream vacation you are looking for... Serenity and bliss on the water, impeccable accommodations, luxurious furniture and decor, high end everything: it's paradise! And there is so much to do: bike riding, swimming, kayaking, relax with a book, play billiards, beach, great restaurants, sightseeing and more. My favorite room is the screened in porch with the perfect breeze and superb view. It was SO relaxing and an amazing oasis! I highly recommend it.

About the host

Hosted by Andrea Shastid Owner

Host profile image
I am originally from Long Is. and after a career in avaition, have opened a seasonal restaurant in Sag Harbor, NY. My husband Jon is retired and a competitive masters swimmer.This is our vacation home but we are now at that age where we enjoy traveling and visiting our 5 grown children. We spend our time living in Kentucky and Costa Rica when not on Shelter Island.

Why they chose this property

This home is simply stunning! Built in 2006 it has every modern conveniece. My family and friends have spent memorable times here boating, waterskiing, sailing, kayaking as well as playing guitars and singing around the outdoor fire pit on the warm evenings so frequent on the island. If you want a relaxing and enjoyable
vacation...this is the house for you.

What makes this property unique

The ideal vacation spot for families. Child friendly home on a mile long cul-de-sac dotted with upscale residences and friendly people. Perfect for summer getaways.

Languages:

English
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