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

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 wooden dock leading to a calm lake with a sailboat docked at the end.
A dining area with a wooden table and chairs, a chandelier, and a view of a garden through large windows.
A spacious living room with large windows, a wooden cabinet, and a dining area with a table and chairs.

Reviews

9.6 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Balcony
  • Arcade/game room
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Washing machine

Explore the area

View 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

Rooms & beds

5 bedrooms (sleeps 12)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

Bedroom 3

2 Single Beds

Bedroom 4

1 Queen Bed

Bedroom 5

1 Queen Bed

TV Room 6

1 Double Futon

3 bathrooms

Bathroom 1

Bathtub or shower · Bathtub · Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area
Garden

Add dates for prices

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About the area

Shelter Island

Located in Shelter Island, this holiday home is on a river. Havens House and East End Seaport Maritime Museum are cultural highlights, and some of the area's activities can be experienced at Shelter Island Country Club and Shelter Island Whale's Tail. Greenport Carousel and Railroad Museum of Long Island are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and cycling nearby.
View more Holiday homes in Shelter IslandOpens in a new window
Map
Shelter Island, NY

What's nearby

  • Shelter Island Historical Society - 3 min drive - 2.5 km
  • Havens House - 3 min drive - 2.5 km
  • Crescent Beach - 3 min drive - 2.9 km
  • Shelter Island Whale's Tail - 3 min drive - 3.2 km
  • Sunset Beach - 3 min drive - 3.2 km

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

Frequently asked questions

Is Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock?

As of 14 Nov 2026, prices found for a 1-night stay for 2 adults at Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock on 23 Nov 2026 start from AU$11,116, 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 Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock?

On-site parking is available at the property.

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

Check-in begins at 5:00 PM.

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

Checkout is at 11:00 AM.

Where is Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock located?

Situated by the ocean, this holiday home is within 2 miles (3 km) of Havens House, Shelter Island Historical Society and Shelter Island Country Club. Sunset Beach and Shelter Island Whale's Tail are also within 3 miles (5 km).

Reviews

9.6

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. 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

9.8/10

Check-in

9.8/10

Communication

10/10

Location

9.6/10

Listing accuracy

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
Beautiful home. Perfect setting for us, our 2 children and their kids. Alot of space. Plenty of room. Central location made it easy to go to the beach, the market and the ferry.
Stayed 6 nights in Jun 2026
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

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Gorgeous home on the bay. Dock and kayaks available. Kitchen range is ideal. A Weber grill was also provided and a pool table was delightful. The home was clean but would benefit from some TLC. The Barrels outside hold dead plants and weeds. I recommend some updates to lamps, bathroom rugs and much greater organization of linen closets and the ample kitchen cabinets. It’s difficult to find anything when there are no labeled cupboards and items are stored with those holding very unlike items. The location is ideal with laundry and both heat and AC at the renter’s disposal. Its greatest features are the back patio and bedrooms on both floors. There is no manual for expectations or information so the owner needs to be contacted with questions or concerns.
Stayed 6 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved John’s house, great for a family, lots of room, many activities, great location, highly recommend
Stayed 6 nights in Jun 2026
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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