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Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock

Shelter Island vacation home with kitchen

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Photo gallery for Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock

A deck with white wicker furniture, including chairs and a sofa, overlooking a lake.
A living room with a beige sofa, a coffee table, and a ceiling fan. There are large windows with a view of greenery outside.
A spacious living room with large windows, a wooden cabinet, and a dining area with a table and chairs.
A dining area with a wooden table and chairs, a chandelier, and a view of a garden through large windows.
A wooden dock leading to a calm lake with a sailboat docked at the end.

Reviews

9.6 out of 10
Exceptional

Entire home

5 bedrooms3 bathroomsSleeps 124700 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space
  • Parking available

Explore the area

View in a map
Shelter Island, NY
  • Place, Shelter Island Historical Society
    ‪3 min drive‬
  • Place, Crescent Beach
    ‪3 min drive‬
  • Place, Sunset Beach
    ‪3 min drive‬
  • Airport, Montauk, NY (MTP)
    ‪67 min drive‬

Room options

About the neighborhood

Shelter Island

Seaside stay .Within 2 miles (3 km) of this Shelter Island vacation home, you'll find Havens House and Shelter Island Historical Society. Shelter Island Country Club and Sunset Beach are also within 2 miles (3 km).
View more Vacation Homes in Shelter IslandOpens in a new window

What's nearby

  • Shelter Island Historical Society - 3 min drive - 1.6 miles
  • Havens House - 3 min drive - 1.6 miles
  • Crescent Beach - 3 min drive - 1.8 miles
  • Shelter Island Country Club - 3 min drive - 1.8 miles
  • Sunset Beach - 3 min drive - 2.0 miles

Getting around

  • Greenport Station - 24 min drive
  • East Hampton, NY (HTO) - 40 min drive

Restaurants

  • ‪Claudio’s Waterfront - ‬25 min drive
  • ‪Goldberg’s Famous Bagels - ‬24 min drive
  • ‪Pridwin Hotel - ‬5 min drive
  • ‪Sunset Beach Restaurant - ‬3 min drive
  • ‪Port Bar & Grill - ‬24 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock

Beautiful Waterfront Home on West Neck Creek on Shelter Island. New deck overlooking West Neck Creek -Great for relaxing or entertaining. Bright & Airy vacation home on private road. Newly decorated with central air conditioning, pool/game room. Large picture windows throughout overlooking water – great vacation home for large family. Deep water dock, six and half feet at low tide on shallow end, for up to 60 boat. Swim, Fish, Sail, Boating. Commercial ice machine, 450 pounds of ice a day for beach, boating or your party!

Restaurants & Shopping, Marina, Golf, Beaches. Luxury home on water. Beautiful sunsets.

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Cliffside Resort Condominiums
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  • Pool
  • Kitchen
  • Pet friendly
  • Parking included
4.5 out of 5, Wonderful, 294 reviews
$333 nightly
The price is $380
Oct 25 - Oct 26
Total with taxes and fees
Cliffside Resort Condominiums

Property amenities

Internet

  • Available in the house: WiFi

Parking and transportation

  • Car required
  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Bedrooms

  • 5 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 3 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Toilet paper
  • Towels provided

Living spaces

  • Fireplace
  • Separate dining area
  • Wood stove

Entertainment

  • Books
  • DVD player
  • Games
  • Stereo
  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near the bay
  • Near the marina
  • Near the ocean
  • On a river

Things to do

  • Arcade/game room
  • Billiards/pool table
  • Kayak
  • Optional golf privileges
  • Birdwatching nearby
  • Cycling nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Scuba diving nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Garden
  • Unit size: 4,700 square feet

Policies

Check-in

Check-in time starts at 5:00 PM

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

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
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
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited.

Property is also known as

Waterfront Home Beautiful W/large Deep Water Dock House
Waterfront Home Beautiful Shelter Island W/large Deep Water Dock
Waterfront Home Beautiful W/large Deep Water Dock
Waterfront Home Beautiful W/large Deep Water Dock House
Waterfront Home Beautiful Shelter Island W/large Deep Water Dock
Waterfront Home Beautiful W/large Deep Water Dock House
Waterfront Home Beautiful W/large Deep Water Dock

Frequently asked questions

How close is Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock to the airport?

This vacation home is 11.2 mi (40-min drive) away from the East Hampton, NY (HTO) airport, the closest popular airport to the property.

Does Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock to the beach?

This vacation home is 3.4 mi (24-min drive) from The Hamptons Beaches and 1.6 mi (3-min drive) from Sunset Beach. Don't forget your sunscreen!

Does Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock?

No, there is no casino at this vacation home.

What time is check-in at Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock?

Check-in begins at 5:00 PM.

Is there free parking at Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock?

Free parking is not available at this vacation home.

Does Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock have a pool?

This vacation home does not have a pool.

Does Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock have a spa?

There are no spa services available at this vacation home.

How close is Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock to downtown Shelter Island?

This vacation home is 0.8 mi away from Shelter Island.

Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 14 out of 16 reviews
Rating 8 - Good. 1 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 1 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

9.6/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location!
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

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

Dock House; Beautiful Setting

The host went all out to make our stay very pleasant. The new oven was great; the house was clean and had thoughtful touches. We enjoyed the “firemen’s” ladder at the dock. The dock is a perfect place for morning coffee or enjoying the evening. The outdoor patio has multiple seating;the upper deck has great views. It was a good place to be with family.
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
John's house was the perfect spot for our family vacation!! The house is situated on West Neck creek and has spectacular sunset views with a lovely patio overlooking the water. We loved swimming and kayaking off of the dock. The house is perfect for a large family as there are multiple "gathering" areas including an upper deck, rec room with pool table, and t.v. room. John's house has a huge kitchen that opens to the living area, with lots of space for everyone to move around. The house is big - 2 bedrooms rooms on the main level and 3 on the upper level! We spent every morning and evening on the beautiful patio and just loved the place. Our family is from Shelter Island, and this is a great Shelter Island house. It was super peaceful at night, and we loved the quiet location. John was very helpful, generous, and responsive to any questions. We can't wait to stay again!!!
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

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

A gem

My family of all ages from infant to senior enjoyed the house immensely. The setting is ideal for family gatherings, both outside and inside. There were plenty of places to go for conversation. The homeowner was very responsive when there was an issue and a minor repair was made that day. He provided the kayaks we requested and plenty of linens were in the linen closet. The bathrooms are a bit dated but the kitchen and laundry room have new appliances. The grills on the patio were put to good use too. The homeowner asked us to call with any concerns or questions and hoped that we would have a good stay. We did and would be very happy to stay here again.
Stayed 9 nights in Jul 2024
Verified review

10/10 Excellent

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

Beautiful Shelter Island get away

Our stay was wonderful with a large family and many kids . The home is very nice with lots of bedrooms and bathrooms. The location was wonderful and beautiful. I was able to get my boat with a 5' draft to the dock. The owner John were excellent with communication.
Stayed 7 nights in Aug 2019
Verified review

10/10 Excellent

This was an amazing house in an incredible location!

This is a great house for any water lovers like me! A beautiful location and home!
Stayed 8 nights in Aug 2018
Archival

10/10 Excellent

Our sailboat behind the house

We loved our week in Shelter Island. The house was perfect for our family with the kids and grandkids! The house was exactly as pictured and we were able to bring our 6' draft sailboat right to the dock behind the house. A great family vacation with lots of communal cooking in the large open kitchen.
Stayed 7 nights in Aug 2017
Archival

10/10 Excellent

Sheldrake Landing: A Sailor's Delight!

We had an awesome time at this house. It's big and beautiful, with plenty of room for a crowd both indoors and out, night and day. Even without our boat, we would have had plenty of fun in the kayaks and fishing/swimming off the pier. But the deep water dock was the real game changer. We had a great time with our sailboat that draws 6'. We were able to make it in on any tide (perhaps cutting a trench through the top of a couple sandbars at low tide, but still ok) and were out of the harbor in about 25 min. The house is convenient to all of the beaches, restaurants and ferries and has parking for at least three cars. We will be delighted to return!
Stayed 14 nights in Aug 2016
Archival

4/10 Poor

Nice house but experience was disheartening.

When renting a high end property there are certain expectations. At first the experience was pleasant with the initial contact and booking of the property. Owner was willing to do a Monday to Monday rental. The check was mailed on time but the owner waited weeks to cash it. The delay in communication started then. The welcome packet email that contained the code to get into the property wasn't emailed until after two emails asking for it were sent. I got the email the week before we were to leave. The house was nice and looked as pictured (although there were a lack of closets in bedrooms as well as all bedrooms upstairs share 1 bathroom). The issues we had with the house was mainly the cleanliness (cobwebs with spiders on lamps, food in dishwasher and garbage in drawers) as you are paying a cleaning fee. Owner was on top of communication while we were there and would answer calls and texts. The biggest issue now is I have contacted the owner 5 times regarding my deposit as it has been almost 2 months since our rental. I received one short email stating "check is in the mail sorry for the delay" on 10-21. I have yet to receive the check on 11-6. I know the mail doesn't take that long and I know the owner has my address. This is not a small amount of money to me. I am really disappointed by this situation as we followed all the rules and I believe we were good renters.
Archival

10/10 Excellent

Perfect Vacation Rental!

The house exceeded my expectations...the pictures don't do it justice. Great house. Could not have asked for more. The kitchen was stocked with everything you need , whether just having a glass of wine or preparing a meal..plenty of pots, dishes, etc. Bedrooms are large and the beds are extremely comfortable. (not always the case with a rental). Having two bedrooms on the first floor was a plus for older guests staying with us. There are 3 separate gathering areas inside the house so we were not all cramped into one space, also made it possible for alone time while staying with 8 other people. The game room was a great place to watch a game or movie on the large flat screen TV. As beautiful as the house is, the location is the best part. Located on a peaceful creek, the patio is a great place to relax and unwind. We spent most of our time outside, swimming, fishing, relaxing in the hammock, and having lots of bbq's. There is a large side yard, perfect for kids to play. The owner was very friendly, so easy to work with and answered all my questions quickly. So happy with the decision to rent this home....Cannot wait to come back!
Archival

10/10 Excellent

Wonderful stay!

We had a fabulous stay in Shelter Island. We had a full house with older parents, young parents, babies and friends and there was room for all. Great large kitchen, tons of space, gorgeous outdoors and wonderful swimming off the dock. The owner was responsive and friendly, made for an excellent stay. We hope to return! Sunsets, stargazing, grilling and tooling around the island were highlights along with plenty of naps in the hammock.
Archival

10/10 Excellent

Great House!

We rented this house over 4th of July week for a family vacation - we were 6 adults and 3 children. We loved it! The house was very comfortable and fully stocked with all the basic needs. It was also clean and very large with different areas to hang out in. Our favorite was the back deck where we had a few BBQ dinners. The views of the creek were very beautiful and it was a convenient place to swim or kayak. The owners were very easy to work with and we look forward to visiting this property again in the future. Loved it!
Archival

10/10 Excellent

Comfy, roomy, well stocked

This was out first experience with VRBO/HomeAway, and we could not have been happier. This home is even nicer in person than in the photos. The view from the kitchen looking out over the creek at sunset is a treat while preparing dinner or having drinks and appetizers. We had 2 three generational families share the space with one family upstairs and the other down. There was ample space for all to sleep. We love to cook and the kitchen had just about every gadget we could have hoped for as well as lots of serving dishes. There were plenty of social areas to get away into smaller groups. The lawn on the back yard is adequately lit to allow activities outdoors after dark. The hammock is lovely. The dock allowed for swimming and kayaking in "God's swimming pool". (My favorite quote from the owners!) The owners were super easy to work with and made sure we were able to reach them quickly if we were to have issues. We highly recommend this property and hope to visit again when we come back to Shelter Island in the future.

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