Title: Breathtaking waterfront 5-bedroom house in charming Shelter Island with pool - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Breathtaking waterfront 5-bedroom house in charming Shelter Island with pool Vacation home with kitchen, near The Hamptons Beaches ## Photo gallery for Breathtaking waterfront 5-bedroom house in charming Shelter Island with pool ![Interior - Breathtaking waterfront 5-bedroom house in charming Shelter Island with pool (Shelter Island)](https://images.trvl-media.com/lodging/116000000/115140000/115140000/115139921/w2791h1063x0y0-2b01e6db.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Exterior - Breathtaking waterfront 5-bedroom house in charming Shelter Island with pool (Shelter Island)](https://images.trvl-media.com/lodging/116000000/115140000/115140000/115139921/e5d40e23.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Breathtaking waterfront 5-bedroom house in charming Shelter Island with pool (Shelter Island)](https://images.trvl-media.com/lodging/116000000/115140000/115140000/115139921/cfbd198f.jpg?impolicy=resizecrop&rw=297&ra=fit) ![5 bedrooms, iron/ironing board, WiFi, bed sheets - Breathtaking waterfront 5-bedroom house in charming Shelter Island with pool (Shelter Island)](https://images.trvl-media.com/lodging/116000000/115140000/115140000/115139921/577b730a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Pool - Breathtaking waterfront 5-bedroom house in charming Shelter Island with pool (Shelter Island)](https://images.trvl-media.com/lodging/116000000/115140000/115140000/115139921/6fc60542.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Consider a stay at Breathtaking waterfront 5-bedroom house in charming Shelter Island with pool and take advantage of a garden, laundry facilities, and a gym. Guests can connect to in-room WiFi. ### Entire home 5 bedrooms7 bathrooms ## Popular amenities - Pool - Kitchen - Washer - Dryer - Air conditioning - Gym ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Breathtaking waterfront 5-bedroom house in charming Shelter Island with pool Experience Shelter Island like a local in this beautiful waterfront home. Main house with 3 bedrooms and 4.5 baths. Guest house with 2 bedrooms and 2 baths. Gunite pool, outdoor grill, beach and dock. Enjoy amenities like a washing machine, heating, fitness room, iron, WiFi, and AC. Immerse yourself in the tranquility of Shelter Island and make unforgettable memories at our dream getaway home. Shelter Island Long Term Rental # 2025-L-0103. ## Property amenities ### Beach - Beach loungers - Beach towels ### Pool/Spa - Pool ### Internet - Available in the house: WiFi ### Parking and transportation - Parking on site ### Kitchen - Blender - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Electric kettle - Ice maker - Kitchenette - Microwave - Oven - Refrigerator - Spices - Stovetop - Toaster ### Bedrooms - 5 bedrooms - Bedsheets provided ### Bathroom - 6.5 bathrooms - Towels provided ### Living spaces - Fireplace ### Entertainment - Smart TV ### Outdoor areas - Balcony - Barbecue grill - Garden - Outdoor furniture ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning - Heating ### Pets - Service animals only (pets not allowed) ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Housekeeping (on request) - Iron/ironing board ### Things to do - Bicycles - Boat - Gym - Kayak - Water sports equipment ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) ### General - Bicycles - Garden - Housekeeping (on request) - Living plant wall ## Similar properties ![Living area](https://images.trvl-media.com/lodging/69000000/68780000/68771500/68771498/46fe7fa7.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Most private house with pool with ocean view Shorewood [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-13&endDate=2026-02-14&selected=68771498&PinnedHotelID=68771498&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/105000000/104230000/104229900/104229861/863e1739.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautiful Shelter Island/Hamptons Beach House Monthly Rental Shorewood - Washer - Dryer - Pet friendly - Air conditioning [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-13&endDate=2026-02-14&selected=104229861&PinnedHotelID=104229861&HadPinnedHotel=true®ionId=-1&adults=2) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/75000000/74100000/74095400/74095357/485c8cc0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Majestic estate in coveted Private North Haven Community, 2 acres of lush... Sag Harbor - Pool - Kitchen - Washer - Dryer [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-13&endDate=2026-02-14&selected=74095357&PinnedHotelID=74095357&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-02-13&endDate=2026-02-14&selected=115139921&PinnedHotelID=115139921&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=115139921,68771498,104229861,74095357) ## Policies ### Check-in Minimum check-in age: 21 ### Check-out Flexible check-out available (contact host to arrange) ### Special check-in instructions The front desk hours vary at this property Guests must contact the property for check-in information To make arrangements for check-in please contact the property ahead of time using the information on the booking confirmation You will receive an email from the host with check-in and check-out instructions Check-out time is flexible; to make arrangements, please contact the property ahead of time using the information on the booking confirmation Information provided by the property may be translated using automated translation tools ### Pets Pets not allowed (service animals are welcome, and are exempt from fees) ### 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 indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property 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 ## About the area Shelter Island is home to this vacation home. Shelter Island Whale's Tail and The Style Bar are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore The Hamptons Beaches and Orient Beach State Park. Sag Harbor Whaling and Historical Museum and East End Seaport Maritime Museum are also worth visiting. [Visit our Shelter Island travel guide](https://www.expedia.ca/Shelter-Island.dx157359) [View more Vacation homes in Shelter Island](https://www.expedia.ca/Shelter-Island-Private-Vacation-Homes.d157359-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6¢er=41.044155,-72.313805&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:aipyFfxjxL%3FS%3FS%40U%3FS%40S%3FU%40S%40UBS%40S%40SBSBUBS%40SBSDSBQDSBSDSDSDQDSDQFSDQFSDQFQFOFQHSFOFOHQHOFQHOHOHOHOJMHOJMHMJMJOJMJKHMLMJKJKLKJKLILKJKLILILIJILGNILGLGLGNGLGLENELGNELENCLCNCNELANENANANALANANAN%3FN%3FN%3FN%3FL%3FN%3FN%40N%40L%40N%40N%40N%40NDL%40NDNBLBNBNDLDLFNDLDNFLFLFLFNFLHLFJHLHLHLHLJJJLHJJLJJJJJLLHLJJLLHNJLHLJLHNJLHPHLHNHNHPFNHPFNFPHPFPFNFPDPFRFPDRDPDRDPDRDRBRDRBPDRBRBR%40RBTBR%40RBR%40R%40T%40R%3FT%40R%40R%3FT%3FR%3FR%3FT%3FR%3FTARAR%3FTARATAPCTARCRCTARCRCPERCRERCREREREPEREPEPGRGPERGPGNGPIPGPGNIPGNINIPILININKNINKLILKLINMLKJILMJKJKLMJKJMHKHMLMHMHMHKFMHMHOFMFMFMFODMFODMDMDODODMBOBODM%40OBOBO%40O%40M%40O%40O%40O%3FM%3FO%3FO%3FO%3FO%3FOAOAMAOAOAOCOCMAOEOCMCOEMEOEMEOEMGMEOGMGMGMGOIMIKGMIMIMIKKMKMIKKMKKMKKMKIMKKKMKOKMIMKMIOKOIMIQIMIQGOIOIQGOGQIQGQGOGQESGQESGQEQESEQESESCSESCSESCQASCSCUCSASAUCQAUAS%3FUAS%3FSAU%3FS%3FU&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=IBAbSEma2KyeEWxUOKT9qH1NZDU=) Shelter Island, NY ### What's nearby - ![0_747774](https://images.trvl-media.com/place/553248635976496850/d01ce793-c89c-46d8-aa7f-c32914f2009c.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) The Hamptons Beaches 11 min walk \- 1.0 km - ![Man watching sailboat on Long Island Sound](https://images.trvl-media.com/place/553248621554204759/ee48f50e-5c27-4bcd-8a17-a99baf567092.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Wades Beach 2 min drive \- 1.5 km - ![Wolffer Estates Vineyard featuring interior views](https://images.trvl-media.com/place/6064497/3867609a-1990-4fbb-846b-be33ce111b82.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Wolffer Estates Vineyard 20 min drive \- 13.7 km - ![Cooper\'s Beach showing a sandy beach and general coastal views](https://images.trvl-media.com/place/6326842/eb826705-7aa2-4648-9064-660387af3569.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Cooper's Beach 36 min drive \- 29.5 km - ![Montauk Point](https://images.trvl-media.com/place/6173408/0ced5e52-1faa-4796-a82d-7f9e4a3c4228.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Montauk Point 53 min drive \- 57.7 km ### Getting around - Greenport Station 28 min drive - East Hampton, NY (HTO) 33 min drive ### Restaurants - Sing City 13 min drive - Tutto il Giorno 13 min drive - K Pasa 12 min drive - Le Bilboquet 13 min drive - Vine Street Cafe 2 min drive ## Frequently asked questions ### Does Breathtaking waterfront 5-bedroom house in charming Shelter Island with pool have a pool? ### Is Breathtaking waterfront 5-bedroom house in charming Shelter Island with pool pet-friendly? ### How much is parking? ### Where is Breathtaking waterfront 5-bedroom house in charming Shelter Island with pool located? ## Have a question? 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