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 ![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) ![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 ![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 Sunset Beach and Crescent 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) ### 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 Shelter Island Whale's Tail. [](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) ### 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) ### 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) ### 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) ### 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 Mashomack Preserve. [](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 £258 9 Feb - 10 Feb 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! (719 reviews) Staying at Gurney's after their many renovations was surprising !! The rooms don't look outdated anymore including the Spa / Pool area - for the price you're paying per night, I appreciated the face lift. Oceanviews from any angle of this hotel site will always be incredible ! Reviewed on 12 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=7033726&PinnedHotelID=7033726&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) muy limpias Reviewed on 8 Jan 2026 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=04%2F02%2F2026&endDate=05%2F02%2F2026&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true®ionId=157359) [](https://expedia.co.uk/Hotel-Search?startDate=04%2F02%2F2026&endDate=05%2F02%2F2026&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true®ionId=157359) ![Montauk Blue Hotel](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Montauk Blue Hotel 108 South Emerson Avenue Montauk NY Stay at this beach hotel in Montauk. Enjoy free Wi-Fi, a beach locale and parking (surcharge). Popular attractions South Edison Beach and Kirk Park Beach are ... 9.2/10 Wonderful! (188 reviews) Great view of sunrise and sunset Reviewed on 19 Jan 2026 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=04%2F02%2F2026&endDate=05%2F02%2F2026&selected=105612509&PinnedHotelID=105612509&HadPinnedHotel=true®ionId=157359) [](https://expedia.co.uk/Hotel-Search?startDate=04%2F02%2F2026&endDate=05%2F02%2F2026&selected=105612509&PinnedHotelID=105612509&HadPinnedHotel=true®ionId=157359) [See all 4,670 properties in Shelter Island](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=22%2F01%2F2026&endDate=23%2F01%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/13000000/12700000/12694100/12694044/96463a2a_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! (1,282 reviews) Great place, shame the restaurant was closed Reviewed on 19 Jan 2026 [](https://expedia.co.uk/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/05048f3e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping Southampton NY Stay at this family-friendly holiday home in Southampton. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Southampton Golf Range and Sebonack ... 9.8/10 Exceptional! (32 reviews) The perfect spot for our niece’s wedding weekend.The property is spacious and well appointed. Close to everything but still feels private. Comfortable beds and sitting areas. The pool was amazing and a great spot to relax between wedding events. We had 7 adults stay there was plenty of room for everyone. ... Reviewed on 26 Sept 2025 [](https://expedia.co.uk/Southampton-Hotels-Delightful-Southampton-Retreat-With-Heated-Pool-Jacuzzi.h101877657.Hotel-Information) ![The SandPiper ](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/9eada5e0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The SandPiper Greenport, NY Stay at this holiday home in Greenport. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Railroad Museum of Long Island and East End Seaport ... 9.6/10 Exceptional! (30 reviews) Terrific service, clean, excellent location. Reviewed on 4 Jan 2026 [](https://expedia.co.uk/Greenport-Hotels-The-SandPiper.h89698318.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=2026-01-21&endDate=2026-01-22)[21 Jan - 22 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=2026-01-21&endDate=2026-01-22) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=2026-01-22&endDate=2026-01-23)[22 Jan - 23 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=2026-01-22&endDate=2026-01-23) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=23%2F01%2F2026&endDate=25%2F01%2F2026)[23 Jan - 25 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=23%2F01%2F2026&endDate=25%2F01%2F2026) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=30%2F01%2F2026&endDate=01%2F02%2F2026)[30 Jan - 1 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157359&startDate=30%2F01%2F2026&endDate=01%2F02%2F2026) ### 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) #### 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) #### 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) #### 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) #### 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) ## 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 ![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 ![Sunset at Rocky Point Rd.](https://images.trvl-media.com/place/6069914/6f926d83-063e-4b71-8708-a460d3e83c0a.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### East Marion ![LongHouse Reserve featuring a park and outdoor art as well as a small group of people](https://images.trvl-media.com/place/6326942/7509b7da-c1b7-4ce3-95d4-0a25d72ea0d7.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Northwest Harbor ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - [5 Star Hotels in Hamptons ](https://www.expedia.co.uk/5Star-Hamptons-Hotels.s50-0-d6056452.Travel-Guide-Filter-Hotels) - 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[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) - [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) - [Essex Steam Train ](https://expedia.co.uk/Essex-Steam-Train-Essex.d6171206.Attraction) - [Ditch Plains Beach ](https://expedia.co.uk/Ditch-Plains-Beach-Montauk.d6326860.Attraction) - [Pleasure Beach ](https://expedia.co.uk/Pleasure-Beach-Waterford.d6328066.Attraction) - [Sunset Beach ](https://expedia.co.uk/Sunset-Beach-Shelter-Island-Heights.d553248626388141313.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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