Title: Shelter Island Heights Vacation Packages & Trips 2025/2026 from CA $680 | Expedia.ca [Hotels in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Vacation-Rentals.d183716.Travel-Guide-VacationRentals)[Things to do in Shelter Island Heights](https://expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)[Shelter Island Heights Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island-Heights.d183716.Car-Rental-Guide) ![](https://images.trvl-media.com/place/157359/8df1734b-1204-4cc5-a5a0-67f90d8a76a3.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Shelter Island Heights Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Brian V. Rowe - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place #### Your Shelter Island Heights Vacation The easiest way to experience this interesting city is with a customized Shelter Island Heights vacation package. Base yourself in the neighborhood of Orient Point, which is good for views, fishing and nature or go someplace else — our package deals are all about you. Make your trip to Shelter Island Heights even more fulfilling by going sightseeing. [67 Steps Beach](https://www.expedia.ca/67-Steps-Beach-Greenport.d553248626388140598.Vacation-Attraction), [Railroad Museum of Long Island](https://www.expedia.ca/Railroad-Museum-Of-Long-Island-Pipes-Cove.d6327144.Vacation-Attraction) and [Kontokosta Winery](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction) are some of the top attractions you'll want to explore. Browse Expedia's wide range of travel options and book your ultimate vacation to Shelter Island Heights today. ## Top Shelter Island Heights Vacation Deals Price found within the past 48 hours. Click for updated prices. ![INNSiDE by Meliá New York Nomad](https://images.trvl-media.com/lodging/13000000/12630000/12628000/12627948/24f1e817_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### INNSiDE by Meliá New York Nomad Manhattan CA $680 per person Jan 14 - Jan 18 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (2,030 reviews) Balcony was amazing! Reviewed on Oct 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-14/2026-01-18/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12627948&paandie=true&dealMarker=oaM_e_NM3hoC9JXU2eBr5cZn-Bw0YzaUtmYVZgZtt-f8DOuEHtUT9tpeE3VKLckv) ![Hyatt Regency Jersey City on the Hudson](https://images.trvl-media.com/lodging/1000000/890000/880300/880227/6f887cd6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Jersey City on the Hudson Downtown Jersey City CA $961 per person Dec 31 - Jan 4 found 2 hours ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 8.4/10 Very Good! (1,546 reviews) Didnt have breakfast food below average for a hyatt. Not very attractive or alluring. PARKING IS 52/DAY GET READY FOR THAT NONSENSE. NEVER AGAIN Reviewed on Oct 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-31/2026-01-04/?FromAirport=YTO&Destination=EWR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=880227&paandie=true&dealMarker=pqldusvS2tnKqL6Byxfl1pFsW4LVWdPAFw6fmUJDvYrSdkJb5fk7D8Yk0wOpr7zS) ![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 $1,469 per person Jan 2 - Jan 5 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.6/10 Exceptional! (151 reviews) A perfect place to stay!! Reviewed on Sep 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-02/2026-01-05/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=96472655&paandie=true&dealMarker=Z3FOz0qxgeQ51dAKnqeRVmo2Zzas8wGwF89K0adXl2ksagXm2V7njpM4LEPt0qVz) ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/7801a5d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge CA $2,171 per person Dec 12 - Dec 15 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (1,012 reviews) Nice hotel , needs a bit of tender love and care ! Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-15/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=15399642&paandie=true&dealMarker=oaM_e_NM3hoC9JXU2eBr5Wpc_OLU72yx8Jkzj6YisqnGfsGWZy3HjEzU-BltnB2l) ## Shelter Island Heights Beach Vacation Escape the stresses of everyday life and let your body, mind and soul unwind on your Shelter Island Heights vacation. There's nothing more invigorating than the smell of salty sea air and the soothing melody of waves lapping at the shore. Plan your trip to Shelter Island Heights the easy way by choosing one of our Shelter Island Heights vacation packages. Many tourists choose to base themselves near Crescent Beach, a must-see just 2 kilometres from the downtown area. ## Things You Should Know About Shelter Island Heights - Check into one of our [Shelter Island Heights beach hotels](https://www.expedia.ca/d183716-tBeachHotel.Travel-Guide-Filter-Hotels?lang=en&rfrr=ATG.LP.BodyContent) to appreciate the best this destination has to offer. Wander along the water's edge and be inspired by the stunning sunrises just moments from your front door. - Alternatively, check out our range of private vacation homes. They're popular with travellers planning a stay in Shelter Island Heights. Consider [Shelter Island House](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Shelter-Island-House.h14997595.Hotel-Information) and [The Chequit](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Chequit.h67569836.Hotel-Information). - There are tons of activities that keep the 1,050 or so residents of Shelter Island Heights occupied. Browsing our [Shelter Island Heights things to do page](null) will let you in on the best of what this place has to offer. - Land great deals with a Shelter Island Heights vacation package. With the money you save, you won't regret indulging in this destination's best offerings. Sunset Beach, Crescent Beach and Crescent Beach are excellent places to start. ## Ready to book your vacation to Shelter Island Heights? Choose your dates ## Shelter Island Heights Hotel Deals ![The Pridwin Hotel](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/fa5a1a49_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Pridwin Hotel 81 Shore Road, Shelter Island Heights, NY 9.4/10 Exceptional! (83 reviews) Overall the places is nice, clean and great views Reviewed on Oct 21, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=12%2F11%2F2025&endDate=13%2F11%2F2025&selected=6473437&PinnedHotelID=6473437&HadPinnedHotel=true®ionId=183716) [](https://expedia.ca/Hotel-Search?startDate=12%2F11%2F2025&endDate=13%2F11%2F2025&selected=6473437&PinnedHotelID=6473437&HadPinnedHotel=true®ionId=183716) ![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 8.8/10 Excellent! (37 reviews) A cozy room with great pillows and quiet. Perfect little place. Reviewed on Oct 10, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=12%2F11%2F2025&endDate=13%2F11%2F2025&selected=67569836&PinnedHotelID=67569836&HadPinnedHotel=true®ionId=183716) [](https://expedia.ca/Hotel-Search?startDate=12%2F11%2F2025&endDate=13%2F11%2F2025&selected=67569836&PinnedHotelID=67569836&HadPinnedHotel=true®ionId=183716) ![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 CA $424 CA $579 total Nov 3 - Nov 4 includes taxes & fees 8.2/10 Very Good! (679 reviews) Unbelievable stay! Staff was very accommodating. Beautiful views. Redone very nicely Reviewed on Oct 26, 2025 [](https://expedia.ca/Hotel-Search?startDate=03%2F11%2F2025&endDate=04%2F11%2F2025&selected=7033726&PinnedHotelID=7033726&HadPinnedHotel=true®ionId=183716) [See all 4,736 properties in Shelter Island Heights](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=30%2F10%2F2025&endDate=31%2F10%2F2025®ionId=183716) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### What to do in Shelter Island Heights ![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 CA $249 per adult **76%** of travellers recommend [](https://expedia.ca/things-to-do/the-hamptons.a330552.activity-details) ![Join a small group full-day wine tour with a certified Sommelier host](https://mediaim.expedia.com/localexpert/1350908/45c47e3f-3e0f-448e-a1a4-64596ec183f0.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Long Island Wine and Food Day Trip with Sommelier host from NYC CA $206 per adult [](https://expedia.ca/things-to-do/long-island-wine-and-food-day-trip-with-sommelier-host-from-nyc.a1350908.activity-details) [See all activities in Shelter Island Heights](https://expedia.ca/things-to-do/search?rid=183716) ## Explore a world of travel with Expedia - 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[The Heights Hotels](https://www.expedia.ca/The-Heights-Shelter-Island-Heights-Hotels.0-n553248635976473534-0.Travel-Guide-Filter-Hotels) - [Hotels near Wades Beach](https://www.expedia.ca/Wades-Beach-Hotels.0-l553248621554204759-0.Travel-Guide-Filter-Hotels) ### Flights - [Flights to Greenport](https://www.expedia.ca/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights) - [Flights to Shelter Island](https://www.expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights) - [Flights from Shelter Island](https://www.expedia.ca/lp/flights/157359/flights-from-shelter-island) - [Flights from Southold](https://www.expedia.ca/lp/flights/183719/flights-from-southold) - [Flights from East Marion](https://www.expedia.ca/lp/flights/6069914/flights-from-east-marion) - [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york) ### Packages - [Bedell Cellars](https://www.expedia.ca/Bedell-Cellars-Cutchogue.d553248621532665643.Vacation-Attraction) - [Castello di Borghese / Hargrave Vineyard](https://www.expedia.ca/Castello-Di-Borghese-Hargrave-Vineyard-Cutchogue.d553248621532665637.Vacation-Attraction) - [Cooper's Beach](https://www.expedia.ca/Coopers-Beach-Southampton.d6326842.Vacation-Attraction) - [East Hampton Main Beach](https://www.expedia.ca/East-Hampton-Main-Beach-East-Hampton.d6326946.Vacation-Attraction) - [East Hampton Vacations](https://www.expedia.ca/East-Hampton.d1524.Destination-Travel-Guides) - [Visit East Marion](https://www.expedia.ca/East-Marion.dx6069914) - [First United Methodist Church](https://www.expedia.ca/First-United-Methodist-Church-East-Hampton.d553248635695603591.Vacation-Attraction) - [Georgica Beach](https://www.expedia.ca/Georgica-Beach-East-Hampton.d553248621554185025.Vacation-Attraction) - [Visit Pipes Cove](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295) - [Hampton Bays Vacations](https://www.expedia.ca/Hampton-Bays.d183681.Destination-Travel-Guides) - [Hamptons Vacations](https://www.expedia.ca/Hamptons.d6056452.Destination-Travel-Guides) - [Havens Beach](https://www.expedia.ca/Havens-Beach-Sag-Harbor.d6326903.Vacation-Attraction) - [Hither Hills State Park](https://www.expedia.ca/Hither-Hills-State-Park-Montauk.d553248621532665771.Vacation-Attraction) - [Hither Woods Preserve](https://www.expedia.ca/Hither-Woods-Preserve-Montauk.d6326910.Vacation-Attraction) - [Kontokosta Winery](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction) - [Longhouse Reserve](https://www.expedia.ca/LongHouse-Reserve-East-Hampton.d6326942.Vacation-Attraction) - [Martha Clara Vineyards](https://www.expedia.ca/Martha-Clara-Vineyards-Riverhead.d6326950.Vacation-Attraction) - [Napeague State Park](https://www.expedia.ca/Napeague-State-Park-Amagansett.d6336519.Vacation-Attraction) - [North Main Street Historic District](https://www.expedia.ca/North-Main-Street-Historic-District-Southampton.d6224101.Vacation-Attraction) - [Old Hook Mill](https://www.expedia.ca/Old-Hook-Mill-North-Main-Street-Historic-District.d6064493.Vacation-Attraction) - [Orient Vacations](https://www.expedia.ca/Orient.d6326191.Destination-Travel-Guides) - [Parrish Art Museum](https://www.expedia.ca/Parrish-Art-Museum-Water-Mill.d6326954.Vacation-Attraction) - [Pindar Vineyards](https://www.expedia.ca/Pindar-Vineyards-Peconic.d6326965.Vacation-Attraction) - [Pollock-Krasner House and Study Center](https://www.expedia.ca/Pollock-Krasner-House-And-Study-Center-East-Hampton.d6064485.Vacation-Attraction) - [Ponquogue Beach](https://www.expedia.ca/Ponquogue-Beach-Hampton-Bays.d6327142.Vacation-Attraction) - [Sag Harbor Vacations](https://www.expedia.ca/Sag-Harbor.d154327.Destination-Travel-Guides) - [Shadmoor State Park](https://www.expedia.ca/Shadmoor-State-Park-Montauk.d6327477.Vacation-Attraction) - [Visit Shelter Island](https://www.expedia.ca/Shelter-Island.dx157359) - [Shinnecock Nation Cultural Center and Museum](https://www.expedia.ca/Shinnecock-Nation-Cultural-Center-And-Museum-Southampton.d6327552.Vacation-Attraction) - [Southampton Arts Center](https://www.expedia.ca/Southampton-Arts-Center-Southampton.d553248629501562732.Vacation-Attraction) - [Southampton Vacations](https://www.expedia.ca/Southampton.d6782.Destination-Travel-Guides) - [Suffolk County Vacations](https://www.expedia.ca/Suffolk-County.d553248635083916458.Destination-Travel-Guides) - [Wolffer Estates Vineyard](https://www.expedia.ca/Wolffer-Estates-Vineyard-Sagaponack.d6064497.Vacation-Attraction) ### Cars - [Car rental Greenport](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide) - [Car rental Shelter Island](https://www.expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide) ### Vacation Rental - [Shelter Island Vacation Rentals](https://www.expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals) ### Other - [Things to do in Greenport](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities) - [Things to do in Shelter Island](https://www.expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)