You're never far from where you need to be with this convenient location.
3 bedrooms2 bathroomsSleeps 8
Popular amenities
Private pool
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Barbecue
Explore the area
Shelter Island, NY
Crescent Beach
Place, Crescent Beach
2 min drive
Shelter Island Country Club
Place, Shelter Island Country Club
3 min drive
Sunset Beach
Place, Sunset Beach
3 min drive
Montauk, NY (MTP)
Airport, Montauk, NY (MTP)
70 min drive
Rooms & beds
3 bedrooms (sleeps 8)
3rd Bedroom
1 Double Bed
Kids Bedroom
1 Single Bed and 1 Single Bunk Bed
Master Bedroom
1 King Bed
2 bathrooms
Bathroom 2
Bathtub or shower · Toilet
Master Bathroom
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Garden
Dining area
About this property
Charming updated home with pool on quiet street. Near Silver Beach
Great house in great location. 3 bedrooms (including one with bunk bed and additional bed) . Open floor plan with updated kitchen and bathrooms. In addition to large pool, great yard and outdoor shower. Short walk to nearby beach or bike to Sunset or Shell Beach. Very friendly quiet neighborhood. Ideal for families with 2-4 kids. We hope our house feels like your home for the time you are here!
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Utilities are paid by renters and will be deducted from the security deposit.
Important information
You need to know
Property # 717549vb
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
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Shelter Island Heights
Silver Beach, a neighbourhood in Shelter Island Heights, is home to this holiday home. The area's natural beauty can be seen at The Hamptons Beaches and East Hampton Main Beach. Shelter Island Whale's Tail and East End Seaport Maritime Museum are also worth visiting. Discover the area's water adventures with power boating, sailing and fishing nearby, or enjoy the great outdoors with hiking/biking trails.
Shelter Island Country Club - 3 min drive - 2.8 km
Sunset Beach - 3 min drive - 3.2 km
Shell Beach - 4 min drive - 3.6 km
Shelter Island Historical Society - 6 min drive - 5.6 km
Getting around
Greenport Station - 25 min drive
East Hampton, NY (HTO) - 44 min drive
Restaurants
Claudio’s Waterfront - 26 min drive
Goldberg’s Famous Bagels - 25 min drive
North Fork Roasting Co. - 32 min drive
Lucharitos - 26 min drive
Aldo's - 26 min drive
Frequently asked questions
Does Charming updated home with pool on quiet street. Near Silver Beach have a pool?
Yes, this property has a pool.
How much does it cost to stay at Charming updated home with pool on quiet street. Near Silver Beach?
As of 20 August 2026, prices found for a 1-night stay for 2 adults at Charming updated home with pool on quiet street. Near Silver Beach on 20 November 2026 start from NZ$8,336, 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 Charming updated home with pool on quiet street. Near Silver Beach pet-friendly?
No, pets are not allowed at this property.
How much is parking at Charming updated home with pool on quiet street. Near Silver Beach?
On-site parking is available at the property.
What time is check-in at Charming updated home with pool on quiet street. Near Silver Beach?
Check-in begins at 4:00 PM.
What time is check-out at Charming updated home with pool on quiet street. Near Silver Beach?
Checkout is at 11:00 AM.
Where is Charming updated home with pool on quiet street. Near Silver Beach located?
Located in Silver Beach, this holiday home is within 2 miles (3 km) of Crescent Beach, Shelter Island Country Club and Sunset Beach. Shell Beach and Shelter Island Whale's Tail are also within 3 miles (5 km).
About the host
Hosted by Paul B
Our family has been coming to Shelter Island for 12 years. We used to rent every summer and decided to buy 3 years ago. We found house we loved on a quiet street that reminds us of our childhood. Our 3 kids love riding their bikes around the neighborhood and beyond. We often ride or walk to the beach in the morning and then sometimes fish or golf in the afternoon. Shelter Island is one of the few places in the area that makes you feel like you have transported into a different time. A quieter time. It is easy to reconnect and read a book or play a board game when all of your day-to-day worries were left behind as you boarded the ferry.
Why they chose this property
5 Pennys Path is special to us because it is a charming house with a pool in a neighborhood that is pretty much self contained. We had a vision for the home and opened up the living area when we redid the kitchen. We also redid the two bathrooms so it feels very new inside. The pool is a big attraction and, fortunately, there is nice flat yard also. We like our neighbors and everyone in the area is very friendly. The location is great. We sometimes don't use the car unless we are going grocery shopping or to play golf. The Silver Beach area is one of the nicest parts of Shelter Island and Shell Beach is probably the best kept secret (shh) on the Island. There is so much to do there including swim, fish, shell, play sports or just relax.
What makes this property unique
The new kitchen, bathrooms and central AC make our home a very easy place to be. The pool right off the back room allows for hours of fun for the family. The house has an open floor plan that allows families to stay connected to each other (instead of the their devices). The location is great for anyone who likes to walk or ride bikes. The neighborhood is unique in that there are 3 parallel roads connected at either end so there is no reason for anyone to enter unless they are a resident or visitor. The Silver Beach area has great quiet beaches and nice fishing. You can walk to Bootlegger's Alley and watch the sunset in less than 5 minutes which, by the way, is a really nice way to end the day. Town and Sunset Beach are short bike rides (and very short drives) away so most major attractions are right nearby. This is a special place to us and we hope it will be to you!