Title: Visit Shelter Island: 2026 Travel Guide for Shelter Island, New York | Expedia.com [Hotels in Shelter Island](https://expedia.com/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island](https://expedia.com/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)[Flights to Shelter Island](https://expedia.com/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Things to do in Shelter Island](https://expedia.com/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)[Car Rentals in Shelter Island](https://expedia.com/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.com/Shelter-Island.d157359.Destination-Travel-Guides) # Shelter Island, NY ## Travel Guide ![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![View of Dering Harbor](https://images.trvl-media.com/place/157359/8df1734b-1204-4cc5-a5a0-67f90d8a76a3.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Great shot of Sunset Beach on Shelter Island from our boat, before heading closer to anchor and swim in. A beautiful little slice of Southern France right here on Long Island Sound! If you get a chance, definitely check this place out.](https://images.trvl-media.com/place/183716/7c4f108a-2c51-4e5b-8cfa-2a22f9251521.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![A beach cafe was airlifted from the South of France and dropped onto this sandy beach on Shelter Island -- complete with pouty-lipped, summer turtle-neck-wearing, aloof, and decorative French serving girls and bar tenderesses. It's quite a see and be scene with a rooftop driftwood bar and dining. Pâté, gzpacho, moule frite, and a cold glass of summer Rosé. It's worth a boat ride from Sag Harbor. ](https://images.trvl-media.com/place/183716/e84e02da-e2d7-4a47-8938-e84980426e5b.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Shelter Island Where to stay Things to do ### Where to stay in Shelter Island ![Center console boat on Long Island, NY. Photographed by drone.](https://images.trvl-media.com/place/553248635976481903/93829460-9892-494c-803a-a3af6b3b8523.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Silver Beach While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach. [](https://expedia.com/Shelter-Island-Heights-Silver-Beach.dx553248635976481903) ![Welcome To The Beach. Driftwood beach hut with handwritten welcome sign. Port Crescent State Park. Port Austin, Michigan.](https://images.trvl-media.com/place/553248635976481214/0fd5766e-1ec1-4630-87ca-616953333ece.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Menantic Creek If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Shell Beach. [](https://expedia.com/Shelter-Island-Menantic-Creek.dx553248635976481214) ![A sweeping view of the natural beauty at Mashomack Preserve on Shelter Island which is situated between the North and South Forks of Long Island, New York.](https://images.trvl-media.com/place/553248635976480820/ef16583d-a1b3-4f29-8d9e-0f21fcceaafc.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Coecles Harbor When in Coecles Harbor, you can plan a visit to Shelter Island Whale's Tail and Gardiner's Bay Country Club, some noteworthy sights in the nearby area. [](https://expedia.com/New-York-Coecles-Harbor.dx553248635976480820) ![view of wetland from the Marine Park Salt Marsh Nature Trail in brooklyn, new york (with gil hodges bridge to the rockaways int he background) cloud reflections in bay, water](https://images.trvl-media.com/place/553248635976470037/504e907d-021d-4378-950f-32bb724622a2.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Hay Beach Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Harbor Brewing Company are two attractions nearby that you can check out. [](https://expedia.com/Shelter-Island-Heights-Hay-Beach.dx553248635976470037) ![Aerial Views of Mamaroneck, New Rochelle, and Larchmont](https://images.trvl-media.com/place/553248635976481937/9210af7b-6de4-447d-b525-19512b2b53b1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Shorewood While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Shell Beach and Mashomack Preserve. [](https://expedia.com/Shelter-Island-Shorewood.dx553248635976481937) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Montclair Colony While Montclair Colony isn't home to many top sights, Sunset Beach and Mashomack Preserve are some notable places to visit nearby. [](https://expedia.com/Shelter-Island-Montclair-Colony.dx553248635976473165) [See our Where To Stay guide](https://expedia.com/Shelter-Island.dx157359.Where-To-Stay?rfrr=TG.LP.Dest.Neighborhoods) - Shelter Island Hotel Deals - Vacation Rentals in Shelter Island ![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/b29cbb53_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Gurney's Montauk Resort & Seawater Spa 290 Old Montauk Highway Montauk NY $413 nightly $472 total Mar 24 - Mar 25 Total with taxes and fees Book a stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Popular attractions Hither Woods Preserve and Hither ... 8.4/10 Very Good! (738 reviews) I took my husband for a relaxing weekend for his birthday at Gurneys Resort. We had an ocean front room with a beautiful view! The room and resort was beautiful and clean. We hung out at GiGis bar a lot and the bar tenders were great! Super friendly and helpful! I loved our stay however I was truly ... Reviewed on Mar 4, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F24%2F2026&endDate=3%2F25%2F2026&selected=7033726&PinnedHotelID=7033726&HadPinnedHotel=true®ionId=157359) ![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Montauk Manor 236 Edgemere St. Montauk NY $168 nightly $192 total Mar 31 - Apr 1 Total with taxes and fees Stay at this aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ... 9.2/10 Wonderful! (1,304 reviews) Amazing! Reviewed on Mar 15, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F31%2F2026&endDate=4%2F1%2F2026&selected=12694044&PinnedHotelID=12694044&HadPinnedHotel=true®ionId=157359) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/fc6ee41c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Water's Edge Resort & Spa 1525 Boston Post Road Westbrook CT $164 nightly $189 total Apr 1 - Apr 2 Total with taxes and fees Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ... 8.8/10 Excellent! (1,001 reviews) Beautiful location, nicely appointed rooms, lovely staff. Food got mixed reviews from our group. Fantastic venue for bridal shower. Reviewed on Mar 16, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&selected=9679841&PinnedHotelID=9679841&HadPinnedHotel=true®ionId=157359) [See all 4,720 properties in Shelter Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F18%2F2026&endDate=3%2F19%2F2026®ionId=157359) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Montauk Manor 236 Edgemere St. Montauk NY Stay at this aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ... 9.2/10 Wonderful! (1,304 reviews) Amazing! Reviewed on Mar 15, 2026 [](https://expedia.com/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Windward Shores Ocean Resort](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/3dd02542_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Windward Shores Ocean Resort 2062 Montauk Highway Amagansett NY Book a stay at this beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ... 8.8/10 Excellent! (310 reviews) When I went to the property it was not shoveled. A challenge to get to the room. I enjoyed the room with minor things that could change. Reviewed on Mar 2, 2026 [](https://expedia.com/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information) ![4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill](https://images.trvl-media.com/lodging/35000000/34800000/34796500/34796404/08fe8e01_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill Westbrook CT Book a stay at this beach cottage in Westbrook. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Westbrook Town Beach and Clinton ... [](https://expedia.com/Westbrook-Hotels-4BR-Beach-Cottage-Sits-On-Private-Beach-Sleeps-12-With-Comfort.h34796404.Hotel-Information) [See all properties in Shelter Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=157359&sort=VACATION_RENTAL) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ## Check Shelter Island hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=2026-03-17&endDate=2026-03-18)[Mar 17 - Mar 18](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=2026-03-17&endDate=2026-03-18) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=2026-03-18&endDate=2026-03-19)[Mar 18 - Mar 19](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=2026-03-18&endDate=2026-03-19) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026)[Mar 20 - Mar 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026)[Mar 27 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026) ### Popular places to visit ![Colorful pebbles and shells on a beach](https://images.trvl-media.com/place/553248621554204761/5a57054c-a374-4fe2-8982-2385bf184bb1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Shell Beach Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. [](https://expedia.com/Shell-Beach-Shelter-Island.d553248621554204761.Vacation-Attraction) ![Man watching sailboat on Long Island Sound](https://images.trvl-media.com/place/553248621554204759/ee48f50e-5c27-4bcd-8a17-a99baf567092.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wades Beach Why not spend a carefree afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. [](https://expedia.com/Wades-Beach-Shelter-Island.d553248621554204759.Vacation-Attraction) #### Gardiner's Bay Country Club Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries. [](https://expedia.com/Gardiners-Bay-Country-Club-Shelter-Island.d6282173.Vacation-Attraction) #### Shelter Island Historical Society You can spend time studying the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums. [](https://expedia.com/Shelter-Island-Historical-Society-Shelter-Island.d553248635961235094.Vacation-Attraction) #### Shelter Island Whale's Tail You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area. [](https://expedia.com/Shelter-Island-Whales-Tail-Shelter-Island.d553248621554204762.Vacation-Attraction) #### Mashomack Preserve Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area. [](https://expedia.com/Mashomack-Preserve-Shelter-Island.d6224462.Vacation-Attraction) ## Cities near Shelter Island ![East Hampton Main Beach](https://images.trvl-media.com/place/6326946/99c13c6c-b8af-41be-9e07-3f762273ab70.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### East Hampton ![entering the harbor in Greenport by](https://images.trvl-media.com/place/110728/0aa2d4a7-1d4b-44b8-97f3-5f27a8c8da85.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Greenport ![Sag Harbor](https://images.trvl-media.com/place/154327/a91ea3b6-915f-4999-ad18-23d61df0621a.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Sag Harbor ![coastal landscape at Greenport at the islands of shelter islands heights, county New York](https://images.trvl-media.com/place/183716/7e82dc91-d6c1-40f0-b4ce-69678c9bd599.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Shelter Island Heights ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotels near Shelter Island Historical Society ](https://www.expedia.com/Shelter-Island-Historical-Society-Hotels.0-l553248635961235094-0.Travel-Guide-Filter-Hotels) - 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[Vacation Homes in Shelter Island Heights ](https://www.expedia.com/Shelter-Island-Heights-Private-Vacation-Homes.d183716-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Hotels with Balconies in Shelter Island Heights ](https://www.expedia.com/Shelter-Island-Heights-Hotels-Hotels-With-Balconies.0-0-d183716-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Houseboats in Shelter Island Heights ](https://www.expedia.com/Shelter-Island-Heights-Houseboats.d183716-aaHouseboats.Travel-Guide-Accommodation) - [Non-Smoking Hotels in Shelter Island Heights ](https://www.expedia.com/Shelter-Island-Heights-Hotels-Smoke-Free-Hotels.0-0-d183716-tSmokeFreeHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Shelter Island Heights ](https://www.expedia.com/Shelter-Island-Heights-Hotels-Golf-Hotel.0-0-d183716-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hotels near Sunset Beach ](https://www.expedia.com/Sunset-Beach-Hotels.0-l553248626388141313-0.Travel-Guide-Filter-Hotels) - [Hotels near Silver Beach ](https://www.expedia.com/Silver-Beach-Shelter-Island-Hotels.0-n553248635976481903-0.Travel-Guide-Filter-Hotels) - [Hotels near Crescent Beach ](https://www.expedia.com/Crescent-Beach-Hotels.0-l553248621554204758-0.Travel-Guide-Filter-Hotels) - [Hotels near Gardiner's Bay Country Club ](https://www.expedia.com/Gardiners-Bay-Country-Club-Hotels.0-l6282173-0.Travel-Guide-Filter-Hotels) - [Greenport Hotels ](https://www.expedia.com/Greenport-Hotels.d110728.Travel-Guide-Hotels) - [Hotels near Hay Beach ](https://www.expedia.com/Hay-Beach-Shelter-Island-Hotels.0-n553248635976470037-0.Travel-Guide-Filter-Hotels) - [Hotels near Pipes Cove ](https://www.expedia.com/Pipes-Cove-Greenport-Hotels.0-n553248635976473295-0.Travel-Guide-Filter-Hotels) - [Hotels near Greenport Station ](https://www.expedia.com/Greenport-Station-Hotels.d6186190.Travel-Guide-Hotels) - [Hotels near East End Seaport Maritime Museum ](https://www.expedia.com/East-End-Seaport-Maritime-Museum-Hotels.0-l6326863-0.Travel-Guide-Filter-Hotels) - [Hotels near Railroad Museum of Long Island ](https://www.expedia.com/Railroad-Museum-Of-Long-Island-Hotels.0-l6327144-0.Travel-Guide-Filter-Hotels) - [Hotels near Greenport Carousel ](https://www.expedia.com/Greenport-Carousel-Hotels.0-l553248635961252285-0.Travel-Guide-Filter-Hotels) - [Hotels near Camera Obscura ](https://www.expedia.com/Camera-Obscura-Hotels.0-l6326819-0.Travel-Guide-Filter-Hotels) - [Resorts & Hotels with Spas in Greenport ](https://www.expedia.com/Greenport-Hotels-Spa-Hotel.0-0-d110728-tSpaHotel.Travel-Guide-Filter-Hotels) - [B&B in Greenport ](https://www.expedia.com/Greenport-Bed-And-Breakfast.d110728-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Beach Hotels in Greenport ](https://www.expedia.com/Greenport-Hotels-Beach-Hotel.0-0-d110728-tBeachHotel.Travel-Guide-Filter-Hotels) - [Family Hotels in Greenport ](https://www.expedia.com/Greenport-Hotels-Family-Hotel.0-0-d110728-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Greenport ](https://www.expedia.com/Greenport-Hotels-Oceanfront-Hotels.0-0-d110728-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Greenport ](https://www.expedia.com/Greenport-Hotels-Winery-Hotel.0-0-d110728-tWineryHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Greenport ](https://www.expedia.com/Greenport-Hotels-Boutique-Hotel.0-0-d110728-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Greenport ](https://www.expedia.com/Greenport-Hotels-Hotel-With-Pool.0-0-d110728-tHotelwithPool.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Greenport ](https://www.expedia.com/5Star-Greenport-Hotels.s50-0-d110728.Travel-Guide-Filter-Hotels) - [Hilton Hotels in Greenport ](https://www.expedia.com/Greenport-Hotels-Hilton-Hotels.0-0-d110728--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Greenport ](https://www.expedia.com/Greenport-Hotels-Cheap-Hotels.0-0-d110728-tCheapHotels.Travel-Guide-Filter-Hotels) - [Cottages in Greenport ](https://www.expedia.com/Greenport-Cottages.d110728-aaCottages.Travel-Guide-Accommodation) - [Condo Rentals in Greenport ](https://www.expedia.com/Greenport-Condos.d110728-aaCondos.Travel-Guide-Accommodation) - [Romantic Hotels in Greenport ](https://www.expedia.com/Greenport-Hotels-Romantic-Hotel.0-0-d110728-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Greenport ](https://www.expedia.com/Greenport-Hotels-Wedding-Hotels.0-0-d110728-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Motels in Greenport ](https://www.expedia.com/Greenport-Motels.d110728-aaMotels.Travel-Guide-Accommodation) - [4 Star Hotels in Greenport ](https://www.expedia.com/4Star-Greenport-Hotels.s40-0-d110728.Travel-Guide-Filter-Hotels) - [Hotels with Fireplaces in Greenport ](https://www.expedia.com/Greenport-Hotels-Hotels-With-Fireplaces.0-0-d110728-tHotelswithFireplaces.Travel-Guide-Filter-Hotels) - [Hotels with Bars in Greenport ](https://www.expedia.com/Greenport-Hotels-Bar-Hotel.0-0-d110728-tBarHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Greenport ](https://www.expedia.com/Greenport-Hotels-Adults-Only-Resorts.0-0-d110728-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Historic Hotels in Greenport ](https://www.expedia.com/Greenport-Hotels-Historic-Hotel.0-0-d110728-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Apartments in Greenport ](https://www.expedia.com/Greenport-Apartments.d110728-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Greenport ](https://www.expedia.com/Greenport-Cabins.d110728-aaCabins.Travel-Guide-Accommodation) - [Luxury Hotels in Greenport ](https://www.expedia.com/Greenport-Hotels-Luxury-Hotel.0-0-d110728-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Greenport ](https://www.expedia.com/Greenport-Hotels-Hotels-With-Hot-Tubs.0-0-d110728-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Flights to Shelter Island Heights ](https://www.expedia.com/Cheap-Flights-To-Shelter-Island-Heights.d183716.Travel-Guide-Flights) - [Flights from Shelter Island Heights ](https://www.expedia.com/lp/flights/183716/flights-from-shelter-island-heights) - [Flights to Greenport ](https://www.expedia.com/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights) - [Shelter Island Historical Society ](https://www.expedia.com/Shelter-Island-Historical-Society-Shelter-Island.d553248635961235094.Vacation-Attraction) - [Havens House ](https://www.expedia.com/Havens-House-Shelter-Island.d6232745.Vacation-Attraction) - [Sylvester Manor ](https://www.expedia.com/Sylvester-Manor-Shelter-Island-Heights.d6282169.Vacation-Attraction) - [Visit Shelter Island Heights ](https://www.expedia.com/Shelter-Island-Heights.dx183716) - [Wades Beach ](https://www.expedia.com/Wades-Beach-Shelter-Island.d553248621554204759.Vacation-Attraction) - [Mashomack Preserve ](https://www.expedia.com/Mashomack-Preserve-Shelter-Island.d6224462.Vacation-Attraction) - [Sunset Beach ](https://www.expedia.com/Sunset-Beach-Shelter-Island-Heights.d553248626388141313.Vacation-Attraction) - [Shell Beach ](https://www.expedia.com/Shell-Beach-Shelter-Island.d553248621554204761.Vacation-Attraction) - [Crescent Beach ](https://www.expedia.com/Crescent-Beach-Shelter-Island-Heights.d553248621554204758.Vacation-Attraction) - [Gardiner's Bay Country Club ](https://www.expedia.com/Gardiners-Bay-Country-Club-Shelter-Island.d6282173.Vacation-Attraction) - [Visit Greenport ](https://www.expedia.com/Greenport.dx110728) - [Railroad Museum of Long Island ](https://www.expedia.com/Railroad-Museum-Of-Long-Island-Pipes-Cove.d6327144.Vacation-Attraction) - [Camera Obscura ](https://www.expedia.com/Camera-Obscura-Greenport.d6326819.Vacation-Attraction) - [Car rentals near Shelter Island Heights ](https://www.expedia.com/Car-Rentals-In-Shelter-Island-Heights.d183716.Car-Rental-Guide) - [Car rentals near Dering Harbor ](https://www.expedia.com/Car-Rentals-In-Dering-Harbor.d553248634998885605.Car-Rental-Guide) - [Car rentals near Greenport ](https://www.expedia.com/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide) - [Enterprise Rental Cars in Greenport ](https://www.expedia.com/Enterprise-Car-Rentals-In-Greenport.d110728-c15.Car-Rental-Guide-Suppliers) - [Shelter Island Heights Vacation Rentals ](https://www.expedia.com/Shelter-Island-Heights-Vacation-Rentals.d183716.Travel-Guide-VacationRentals) - [Greenport Vacation Rentals ](https://www.expedia.com/Greenport-Vacation-Rentals.d110728.Travel-Guide-VacationRentals) - [Things to do in Greenport ](https://www.expedia.com/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities) - Cities near Shelter Island - Places of interest [East Hampton](https://expedia.com/East-Hampton.dx1524)[Greenport](https://expedia.com/Greenport.dx110728)[Sag Harbor](https://expedia.com/Sag-Harbor.dx154327)[Shelter Island Heights](https://expedia.com/Shelter-Island-Heights.dx183716)[Southold](https://expedia.com/Southold.dx183719)[East Marion](https://expedia.com/East-Marion.dx6069914)[Noyack](https://expedia.com/Noyack.dx6217344) - [Gardiner's Bay Country Club ](https://expedia.com/Gardiners-Bay-Country-Club-Shelter-Island.d6282173.Vacation-Attraction) - [Shelter Island Historical Society ](https://expedia.com/Shelter-Island-Historical-Society-Shelter-Island.d553248635961235094.Vacation-Attraction) - [Mashomack Preserve ](https://expedia.com/Mashomack-Preserve-Shelter-Island.d6224462.Vacation-Attraction) - [Havens House ](https://expedia.com/Havens-House-Shelter-Island.d6232745.Vacation-Attraction) - [Shell Beach ](https://expedia.com/Shell-Beach-Shelter-Island.d553248621554204761.Vacation-Attraction) - [Wades Beach ](https://expedia.com/Wades-Beach-Shelter-Island.d553248621554204759.Vacation-Attraction) - [Ocean Beach Park ](https://expedia.com/Ocean-Beach-Park-New-London.d6071449.Vacation-Attraction) - [Cooper's Beach ](https://expedia.com/Coopers-Beach-Southampton.d6326842.Vacation-Attraction) - [East Hampton Main Beach ](https://expedia.com/East-Hampton-Main-Beach-East-Hampton.d6326946.Vacation-Attraction) - [Hammonasset Beach State Park ](https://expedia.com/Hammonasset-Beach-State-Park-Madison.d553248621557934267.Vacation-Attraction) - [Shinnecock Hills Golf Course ](https://expedia.com/Shinnecock-Hills-Golf-Course-Southampton.d6327546.Vacation-Attraction) - [Wolffer Estates Vineyard ](https://expedia.com/Wolffer-Estates-Vineyard-Sagaponack.d6064497.Vacation-Attraction) - [Hither Hills State Park ](https://expedia.com/Hither-Hills-State-Park-Montauk.d553248621532665771.Vacation-Attraction) - [Essex Steam Train ](https://expedia.com/Essex-Steam-Train-Essex.d6171206.Vacation-Attraction) - [Ditch Plains Beach ](https://expedia.com/Ditch-Plains-Beach-Montauk.d6326860.Vacation-Attraction) - [Pleasure Beach ](https://expedia.com/Pleasure-Beach-Waterford.d6328066.Vacation-Attraction) - [Connecticut River ](https://expedia.com/Connecticut-River-United-States-of-America.d553248621555565605.Vacation-Attraction) - [Raphael Winery ](https://expedia.com/Raphael-Winery-Peconic.d6327146.Vacation-Attraction) - [Lake Montauk ](https://expedia.com/Lake-Montauk-Montauk.d553248621532665766.Vacation-Attraction) - [Shinnecock Nation Cultural Center and Museum ](https://expedia.com/Shinnecock-Nation-Cultural-Center-And-Museum-Southampton.d6327552.Vacation-Attraction) - [South Edison Beach ](https://expedia.com/South-Edison-Beach-Montauk.d553248621554184988.Vacation-Attraction) - [The Jewish Center of the Hamptons ](https://expedia.com/The-Jewish-Center-Of-The-Hamptons-East-Hampton.d553248621532665726.Vacation-Attraction) - [Parrish Art Museum ](https://expedia.com/Parrish-Art-Museum-Water-Mill.d6326954.Vacation-Attraction) - [Rocky Neck State Park ](https://expedia.com/Rocky-Neck-State-Park-Niantic.d6328112.Vacation-Attraction) - [Westbrook Town Beach ](https://expedia.com/Westbrook-Town-Beach-Westbrook-Center.d553248635975977719.Vacation-Attraction) - [Macari Vineyards ](https://expedia.com/Macari-Vineyards-Mattituck.d6326944.Vacation-Attraction) - [Kontokosta Winery ](https://expedia.com/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction) - [Sunset Beach ](https://expedia.com/Sunset-Beach-Shelter-Island-Heights.d553248626388141313.Vacation-Attraction) - [Clinton Crossing Premium Outlets ](https://expedia.com/Clinton-Crossing-Premium-Outlets-Clinton.d6276899.Vacation-Attraction)