Title: Shelter Island Travel Guide: Best of Shelter Island, New York Travel 2026 | Expedia.co.uk [Hotels in Shelter Island](https://expedia.co.uk/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Holiday Rentals in Shelter Island](https://expedia.co.uk/Shelter-Island-Holiday-Rentals.d157359.Travel-Guide-HolidayRentals)[Flights to Shelter Island](https://expedia.co.uk/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Shelter Island Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Shelter-Island.d157359.Car-Hire-Guide)[Shelter Island Holidays](https://expedia.co.uk/Shelter-Island.d157359.Holidays-City-Breaks) # Shelter Island Travel Guide ## Tourist Guide ![Photo by tom owens](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by tom owens](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg) ![Photo by Rich Barton](https://mediaim.expedia.com/destination/2/1263ceec78a2ea3b58ee516bf8c95425.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Rich Barton](https://mediaim.expedia.com/destination/2/1263ceec78a2ea3b58ee516bf8c95425.jpg) ## Visit Shelter Island Where to stay Things to do ### Where to stay in Shelter Island ![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) ### Silver Beach While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach. [](https://expedia.co.uk/Shelter-Island-Heights-Silver-Beach.dx553248635976481903) ![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) ### Coecles Harbor While Coecles Harbor isn't home to many top sights, Shelter Island Whale's Tail and Gardiner's Bay Country Club are some notable places to visit nearby. [](https://expedia.co.uk/New-York-Coecles-Harbor.dx553248635976480820) ![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) ### Menantic Creek While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Sunset Beach and Crescent Beach. [](https://expedia.co.uk/Shelter-Island-Menantic-Creek.dx553248635976481214) ![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) ### Shorewood While Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Mashomack Preserve and Sunset Beach. [](https://expedia.co.uk/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) ### Hay Beach When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area. [](https://expedia.co.uk/Shelter-Island-Heights-Hay-Beach.dx553248635976470037) ![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 If you're looking for some top things to see and do in Montclair Colony and surrounding area, you can visit Sunset Beach and Crescent Beach. [](https://expedia.co.uk/Shelter-Island-Heights-Montclair-Colony.dx553248635976473165) - Top hotels in Shelter Island - Top Holiday Rentals in Shelter Island ![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Gurney's Montauk Resort & Seawater Spa 290 Old Montauk Highway Montauk NY £366 21 Dec - 22 Dec includes taxes & fees 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 Hills ... 8.2/10 Very Good! (701 reviews) Everything was perfect. Staff, room, experience. Will definitely stay again. Reviewed on 14 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=7033726&PinnedHotelID=7033726&HadPinnedHotel=true®ionId=157359) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Water's Edge Resort & Spa 1525 Boston Post Road Westbrook CT £157 17 Dec - 18 Dec includes taxes & fees Stay at this beach resort in Westbrook. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ... 8.8/10 Excellent! (1,004 reviews) Holiday family tradition! Reviewed on 12 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=17%2F12%2F2025&endDate=18%2F12%2F2025&selected=9679841&PinnedHotelID=9679841&HadPinnedHotel=true®ionId=157359) ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pier Blue Inn Old Saybrook - Essex 1430 Boston Post Rd Old Saybrook CT Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ... 7.8/10 Good! (1,001 reviews) Clean and pleasant place staff is accommodating and professional a good value on the shoreline Reviewed on 10 Dec 2025 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true®ionId=157359) [](https://expedia.co.uk/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true®ionId=157359) [See all 4,676 properties in Shelter Island](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®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/13000000/12700000/12694100/12694044/96463a2a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Montauk Manor 236 Edgemere St. Montauk NY Stay at this aparthotel in Montauk. Enjoy free Wi-Fi, an outdoor pool and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms in ... 9/10 Wonderful! (1,268 reviews) The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable Reviewed on 15 Dec 2025 [](https://expedia.co.uk/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Cliffside Resort Condominiums](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/1638a16b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cliffside Resort Condominiums 61475 Route 48 (North Road) Greenport NY Stay at this beach aparthotel in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and East End ... 8.8/10 Excellent! (249 reviews) The unit was cute and well-appointed. I would recommend a new refrigerator in the unit, as the freezer door was broken. Reviewed on 12 Nov 2025 [](https://expedia.co.uk/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information) ![Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available ](https://images.trvl-media.com/lodging/29000000/28070000/28067800/28067732/e4971697_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available Sag Harbor NY Stay at this family-friendly holiday home in Sagaponack. Enjoy free Wi-Fi, private pools and a fitness centre. Our guests praise the helpful staff in their reviews. ... 10/10 Exceptional! (87 reviews) Property was very responsible and amazing to work with!! Reviewed on 29 Sept 2025 [](https://expedia.co.uk/Sagaponack-Hotels-Summer-2025-Now-Available-Wolffer-Vineyard-Close.h28067732.Hotel-Information) [See all properties in Shelter Island](https://expedia.co.uk/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.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=2025-12-16&endDate=2025-12-17)[16 Dec - 17 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=2025-12-16&endDate=2025-12-17) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=2025-12-17&endDate=2025-12-18)[17 Dec - 18 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=2025-12-17&endDate=2025-12-18) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025)[19 Dec - 21 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025)[26 Dec - 28 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025) ### Popular places to visit #### 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.co.uk/Gardiners-Bay-Country-Club-Shelter-Island.d6282173.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.co.uk/Mashomack-Preserve-Shelter-Island.d6224462.Attraction) #### Shelter Island Historical Society You can spend time browsing 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.co.uk/Shelter-Island-Historical-Society-Shelter-Island.d553248635961235094.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.co.uk/Shelter-Island-Whales-Tail-Shelter-Island.d553248621554204762.Attraction) #### Shell Beach Why not spend a care-free afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. [](https://expedia.co.uk/Shell-Beach-Shelter-Island.d553248621554204761.Attraction) #### Wades Beach Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. [](https://expedia.co.uk/Wades-Beach-Shelter-Island.d553248621554204759.Attraction) ### Things to do ![The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC](https://mediaim.expedia.com/localexpert/330552/c1afebb8-4a31-47a1-af1e-6d13dd7d5c25.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC £135 per adult **76%** of travellers recommend [](https://expedia.co.uk/things-to-do/the-hamptons.a330552.activity-details) [See all activities in Shelter Island](https://expedia.co.uk/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities) ## Cities near Shelter Island ![East Hampton Main Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252521-Long-Island.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### East Hampton ![Sag Harbor](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252775-Sag-Harbor.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Sag Harbor ![Photo by Benny Goh ](https://mediaim.expedia.com/destination/2/64a7a541b17dabdb743e9908dec5b467.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### East Marion ![Northwest Harbor](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252947-Longhouse-Reserve.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Northwest Harbor ## Explore a world of travel with Expedia - 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[Visit Eastport ](https://www.expedia.co.uk/Eastport.dx6223775) - [Visit Pipes Cove ](https://www.expedia.co.uk/Greenport-Pipes-Cove.dx553248635976473295) - [Visit Hampton Bays ](https://www.expedia.co.uk/Hampton-Bays.dx183681) - [Hamptons Holidays ](https://www.expedia.co.uk/Hamptons.d6056452.Holidays-City-Breaks) - [Visit Hamptons ](https://www.expedia.co.uk/Hamptons.dx6056452) - [Havens House ](https://www.expedia.co.uk/Havens-House-Shelter-Island.d6232745.Attraction) - [Island's End Golf and Country Club ](https://www.expedia.co.uk/Islands-End-Golf-And-Country-Club-East-Marion.d6326920.Attraction) - [Visit Jamesport ](https://www.expedia.co.uk/Jamesport.dx6323751) - [Visit Manorville ](https://www.expedia.co.uk/Manorville.dx6173369) - [Visit Mastic Beach ](https://www.expedia.co.uk/Mastic-Beach.dx6327542) - [Visit Culloden Shores ](https://www.expedia.co.uk/Montauk-Culloden-Shores.dx553248635976472450) - [Visit Montauk ](https://www.expedia.co.uk/Montauk.dx10637) - [Visit New Suffolk ](https://www.expedia.co.uk/New-Suffolk.dx3000449151) - [New York Holidays ](https://www.expedia.co.uk/New-York.d178293.Holidays-City-Breaks) - [Visit Northwest Harbor ](https://www.expedia.co.uk/Northwest-Harbor.dx553248634999208731) - [Visit Quogue ](https://www.expedia.co.uk/Quogue.dx183707) - [Visit Remsenburg ](https://www.expedia.co.uk/Remsenburg.dx3000449487) - [Visit Rocky Point ](https://www.expedia.co.uk/Rocky-Point.dx6287456) - [Sag Harbor Holidays ](https://www.expedia.co.uk/Sag-Harbor.d154327.Holidays-City-Breaks) - [Visit Sag Harbor ](https://www.expedia.co.uk/Sag-Harbor.dx154327) - [Shelter Island Historical Society ](https://www.expedia.co.uk/Shelter-Island-Historical-Society-Shelter-Island.d553248635961235094.Attraction) - [Visit Southampton ](https://www.expedia.co.uk/Southampton.dx6782) - [Southold Holidays ](https://www.expedia.co.uk/Southold.d183719.Holidays-City-Breaks) - [Visit Suffolk County ](https://www.expedia.co.uk/Suffolk-County.dx553248635083916458) - [Sunset Beach ](https://www.expedia.co.uk/Sunset-Beach-Shelter-Island-Heights.d553248626388141313.Attraction) - [Visit Village of Southampton ](https://www.expedia.co.uk/Village-Of-Southampton.dx553248635931928630) - [Visit Wading River ](https://www.expedia.co.uk/Wading-River.dx183729) - [Visit Water Mill ](https://www.expedia.co.uk/Water-Mill.dx3000351347) - [Visit Westhampton Beach ](https://www.expedia.co.uk/Westhampton-Beach.dx6084385) - [Visit Westhampton ](https://www.expedia.co.uk/Westhampton.dx6140695) - [All inclusive Holiday Packages Hamptons ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/6056452/Hamptons) - [Car hire Cutchogue ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Cutchogue.d183659.Car-Hire-Guide) - [Car hire Greenport ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Greenport.d110728.Car-Hire-Guide) - [Car hire near Hamptons ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Hamptons.d6056452.Car-Hire-Guide) - [Car hire Orient ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Orient.d6326191.Car-Hire-Guide) - [Car hire Sag Harbor ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Sag-Harbor.d154327.Car-Hire-Guide) - [Convertible Car Hire in Hamptons ](https://www.expedia.co.uk/Convertible-Car-Rentals-In-Hamptons.d6056452-tConvertible.Car-Rental-Guide-Class) - [Luxury Car Hire in Hamptons ](https://www.expedia.co.uk/Luxury-Car-Rentals-In-Hamptons.d6056452-tLuxury.Car-Rental-Guide-Class) - [Sixt Rental Cars in Hamptons ](https://www.expedia.co.uk/Sixt-Car-Rentals-In-Hamptons.d6056452-c35.Car-Rental-Guide-Suppliers) - [East Marion Holiday Rentals ](https://www.expedia.co.uk/East-Marion-Holiday-Rentals.d6069914.Travel-Guide-HolidayRentals) - [Hamptons Holiday Rentals ](https://www.expedia.co.uk/Hamptons-Holiday-Rentals.d6056452.Travel-Guide-HolidayRentals) - [Sag Harbor Holiday Rentals ](https://www.expedia.co.uk/Sag-Harbor-Holiday-Rentals.d154327.Travel-Guide-HolidayRentals) - [Shelter Island Heights Holiday Rentals ](https://www.expedia.co.uk/Shelter-Island-Heights-Holiday-Rentals.d183716.Travel-Guide-HolidayRentals) - [Southold Holiday Rentals ](https://www.expedia.co.uk/Southold-Holiday-Rentals.d183719.Travel-Guide-HolidayRentals) - [Things to do in Hamptons ](https://www.expedia.co.uk/Things-To-Do-In-Hamptons.d6056452.Travel-Guide-Activities) - [Things to do in Sag Harbor ](https://www.expedia.co.uk/Things-To-Do-In-Sag-Harbor.d154327.Travel-Guide-Activities) - Cities near Shelter Island - Places of interest [East Hampton](https://expedia.co.uk/East-Hampton.dx1524)[Sag Harbor](https://expedia.co.uk/Sag-Harbor.dx154327)[East Marion](https://expedia.co.uk/East-Marion.dx6069914)[Northwest Harbor](https://expedia.co.uk/Northwest-Harbor.dx553248634999208731) - [Shelter Island Historical Society ](https://expedia.co.uk/Shelter-Island-Historical-Society-Shelter-Island.d553248635961235094.Attraction) - [Havens House ](https://expedia.co.uk/Havens-House-Shelter-Island.d6232745.Attraction) - [Cooper's Beach ](https://expedia.co.uk/Coopers-Beach-Southampton.d6326842.Attraction) - [Ocean Beach Park ](https://expedia.co.uk/Ocean-Beach-Park-New-London.d6071449.Attraction) - [Essex Steam Train ](https://expedia.co.uk/Essex-Steam-Train-Essex.d6171206.Attraction) - [East Hampton Main Beach ](https://expedia.co.uk/East-Hampton-Main-Beach-East-Hampton.d6326946.Attraction) - [Wolffer Estates Vineyard ](https://expedia.co.uk/Wolffer-Estates-Vineyard-Sagaponack.d6064497.Attraction) - [Shinnecock Hills Golf Course ](https://expedia.co.uk/Shinnecock-Hills-Golf-Course-Southampton.d6327546.Attraction) - [Hither Hills State Park ](https://expedia.co.uk/Hither-Hills-State-Park-Montauk.d553248621532665771.Attraction) - [Ditch Plains Beach ](https://expedia.co.uk/Ditch-Plains-Beach-Montauk.d6326860.Attraction) - [Lake Montauk ](https://expedia.co.uk/Lake-Montauk-Montauk.d553248621532665766.Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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