Shelter Island Retreat w/ Outdoor Pool!

Property ID: 486153Shelter IslandNYUS
Sleeps 105 BR6.5 BA
Book with confidence

Most trips qualify for free 48 hour cancellation. Add dates for more information.


If you’re looking to escape bustling city life, book this 5-bedroom, 6.5-bath home in the Hamptons area! This Shelter Island vacation rental features an office and free WiFi, as well as amenities like a game room and pool to ensure a productive and restorative stay. With fun activities year-round, you can kayak on the nearby ocean, sip on some wine at the Wölffer Estate Vineyard, witness stunning views from Montauk Point, catch a Polo match, or get your holiday shopping done in the Hamptons!


  • Washer
  • Private Outdoor Pool
  • Deck
  • Kitchen
  • Near Ocean
  • Beachfront
  • Wireless Internet (WIFI)
  • Laptop Friendly
  • Essentials
  • Central Heating
  • Central Air Conditioning
  • Cable/Satellite TV
  • Self Check-In


Location Details

THINGS TO SEE + DO: Sylvester Manor Educational Farm - farm stand + theatre + live music in summer months (4 miles), Shelter Island Historical Society (5 miles), Horton Point Lighthouse Nautical Museum (12 miles), The Hamptons (16 miles), Parrish Art Museum (18 miles), Long Island Aquarium (29 miles), Montauk Point Lighthouse Museum (37 miles)

GET OUTSIDE: Lower Beach (1 mile), Upper Beach (3 miles), Coecles Harbor Marina & Boatyard (4 miles), Mashomack Preserve Entrance - walking trails (5 miles), 67 Steps Beach (8 miles), Sagg Main Beach - surfing, deep sea fishing, water sports (17 miles)

WINE & DINE: Ram's Head Inn (0.9 miles), Marie Eiffel Market (5 miles), Vine Street Cafe (5 miles), Greenport Harbor Brewing Company (7 miles), Kontokosta Winery (8 miles), One Woman Winery Greenport (10 miles), The Old Field Vineyards (10 miles), Sparkling Pointe Vineyards & Winery (12 miles), Channing Daughters Winery (13 miles), Wölffer Estate Vineyard (14 miles)

AIRPORTS: Long Island MacArthur Airport (58 miles), Laguardia Airport (101 miles)


2 reviews
  • Highly recommend!


    We had a wonderful time at this beautiful house. Our family came together from Germany and NYC to spend two weeks here and we would come back any time. The bedrooms were comfortable and each comes with its own bathroom. The kitchen is perfectly equipped. The terrace made for wonderful BBQs and the pool is a delight. Thanks for a wonderful stay!

    Published September 13, 2023
  • The perfect getaway


    Though we loved our outings on and around Shelter Island, we would have been just as happy never leaving the property! Our group enjoyed lazy days by the pool and delicious meals cooked at home in the gorgeous kitchen. Ashley was super responsive throughout the weekend, ensuring we had everything we needed. We just checked out last week and are already looking for a week we can come back next year (and hopefully stay even longer).

    Published June 10, 2023
  • 1

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2 reviews

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Select Guests
  • This property has a maximum occupancy of 10 guests, not including infants.
  • Pets are not allowed at this property.
Ages 2-12