Title: Shelter Island Whale's Tail in Shelter Island - Tours and Activities | Expedia.ca [Shelter Island Whale's Tail Hotels](https://expedia.ca/Shelter-Island-Whales-Tail-Hotels.0-l553248621554204762-0.Travel-Guide-Filter-Hotels)[Flights to Shelter Island](https://expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Things to do in Shelter Island](https://expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)[Shelter Island Whale's Tail Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island-Whales-Tail.d553248621554204762.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.ca/Shelter-Island.d157359.Destination-Travel-Guides) # Shelter Island Whale's Tail Tours and Activities ## Visit Shelter Island Whale's Tail Activities [Shelter Island travel guide](https://expedia.ca/Shelter-Island.dx157359) --- --- ## Plan a trip to see Shelter Island Whale's Tail Price found within the past 48 hours. Click for updated prices. ![Loews Regency New York Hotel](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Loews Regency New York Hotel Manhattan CA $1,622 per person Jan 15 - Jan 22 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9/10 Wonderful! (1,002 reviews) helpful staff, nice rooms, location Reviewed on Nov 24, 2025 ![Lotte New York Palace](https://images.trvl-media.com/lodging/1000000/10000/4900/4818/w1695h1110x0y0-027534be_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lotte New York Palace Manhattan CA $1,751 per person Jan 15 - Jan 22 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9/10 Wonderful! (1,723 reviews) Beautiful, Historic property. Staff was outstanding. Great location. We will stay there again Reviewed on Dec 15, 2025 ![The Fifth Avenue Hotel](https://images.trvl-media.com/lodging/97000000/96480000/96472700/96472655/d0a5c1e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Fifth Avenue Hotel Manhattan CA $2,298 per person Jan 25 - Jan 30 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to New York (JFK) 9.6/10 Exceptional! (159 reviews) We had a great stay. Room was comfortable and had what we needed. The staff was professional and some were exceptional. Our room attendant, Nini, stood out as making our stay memorable with her professional work ethic and kindness. Would stay here again. Also enjoyed the restaurant Reviewed on Dec 13, 2025 ### Popular places to visit #### Sylvester Manor You can find out about the history of Shelter Island Heights when you stop by Sylvester Manor. Stroll along the beaches or discover the area's sunsets. [](https://expedia.ca/Sylvester-Manor-Shelter-Island-Heights.d6282169.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.ca/Shelter-Island-Historical-Society-Shelter-Island.d553248635961235094.Vacation-Attraction) #### Havens House You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries. [](https://expedia.ca/Havens-House-Shelter-Island.d6232745.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.ca/Gardiners-Bay-Country-Club-Shelter-Island.d6282173.Vacation-Attraction) #### Menhadden Lane Beach Why not spend a carefree afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights? [](https://expedia.ca/Menhadden-Lane-Beach-Shelter-Island-Heights.d553248621554204760.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.ca/Mashomack-Preserve-Shelter-Island.d6224462.Vacation-Attraction) --- ## Best Lodging Options Near Shelter Island Whale's Tail ## Check availability on hotels close to Shelter Island Whale's Tail [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621554204762&startDate=2025-12-16&endDate=2025-12-17)[Dec 16 - Dec 17](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621554204762&startDate=2025-12-16&endDate=2025-12-17) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621554204762&startDate=2025-12-17&endDate=2025-12-18)[Dec 17 - Dec 18](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621554204762&startDate=2025-12-17&endDate=2025-12-18) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621554204762&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025)[Dec 19 - Dec 21](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621554204762&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621554204762&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025)[Dec 26 - Dec 28](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621554204762&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025) ![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Harbor Front Inn 209 Front St Greenport NY [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sound View Greenport 58775 County Rd 48 Greenport NY [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![The Chequit](https://images.trvl-media.com/lodging/68000000/67570000/67569900/67569836/3084ead9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Chequit 23 Grand Ave Shelter Island Heights NY [](https://expedia.ca/Shelter-Island-Heights-Hotels-The-Chequit.h67569836.Hotel-Information) ![House on Chase Creek](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/51be5ca3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### House on Chase Creek 3 Locust Avenue Shelter Island Heights NY [](https://expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information) ![Shelter Island House](https://images.trvl-media.com/lodging/15000000/15000000/14997600/14997595/efd291ed_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Shelter Island House 11 Stearns Point Rd Shelter Island Heights NY [](https://expedia.ca/Shelter-Island-Heights-Hotels-Shelter-Island-House.h14997595.Hotel-Information) ![Huge Island Getaway Pool Hot Tub Walk To Beach](https://images.trvl-media.com/lodging/39000000/38280000/38273400/38273326/c3065089_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Huge Island Getaway Pool Hot Tub Walk To Beach Shelter Island NY [](https://expedia.ca/Shelter-Island-Hotels-Huge-Island-Getaway-Pool-Hot-Tub-Walk-To-Beach.h38273326.Hotel-Information) ![The Menhaden](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Menhaden 207 Front St Greenport NY [](https://expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information) ![Sunset Beach Hotel ](https://images.trvl-media.com/lodging/105000000/104500000/104494000/104493980/46bb9c1b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sunset Beach Hotel 35 Shore Rd Shelter Island NY [](https://expedia.ca/Shelter-Island-Hotels-Sunset-Beach-Hotel.h104493980.Hotel-Information) ![Waterfront House With Dock And Private Beach](https://images.trvl-media.com/lodging/34000000/34000000/33996200/33996173/567faece_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront House With Dock And Private Beach Shelter Island NY [](https://expedia.ca/Shelter-Island-Hotels-Waterfront-House-With-Dock-And-Private-Beach.h33996173.Hotel-Information) [See all 2,522 properties in Shelter Island Whale's Tail](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248621554204762) 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.