Title: Shelter Island Heights Vacation Packages & Trips 2025/2026 from CA $599 | 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. ![Millennium Hilton New York One UN Plaza](https://images.trvl-media.com/lodging/1000000/10000/1700/1639/ca159422_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Millennium Hilton New York One UN Plaza Manhattan CA $599 per person Feb 13 - Feb 16 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (NYC) 16.4/10 Exceptional! (1,951 reviews) One of my favorite places to stay at actually. Thanms Reviewed on Nov 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-13/2026-02-16/?FromAirport=YHM&Destination=NYC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1639&paandie=true&dealMarker=XZxcnJcnSxQDwlyqA2jJfLd1CvYQwr57MO4cAGmVx1IDA9LyBQmH_3zZPnJQP3_j) ![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 $689 per person Feb 13 - Feb 16 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (NYC) 18.4/10 Exceptional! (2,008 reviews) Had a very nice view. Hotel very central and calm Reviewed on Nov 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-13/2026-02-16/?FromAirport=YHM&Destination=NYC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12627948&paandie=true&dealMarker=XZxcnJcnSxQDwlyqA2jJfDu9fTayoZ25qvC7eCkrYY2su4FN1YrnzcOCWuRFOJfU) ![Radio Hotel](https://images.trvl-media.com/lodging/74000000/73540000/73530400/73530346/e6a69d63_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Radio Hotel Manhattan CA $1,190 per person Dec 20 - Dec 26 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to New York (NYC) 17.2/10 Exceptional! (2,613 reviews) I’m honestly tempted to gatekeep this place because it’s such a gem. I was pleasantly surprised by how much I enjoyed my stay. The room was clean, spacious by NYC standards, and had a nice mid-to-modern vibe. The staff was great — attentive, kind, and fast. I requested room service and it happened quickly, and when I realized I was missing something from the room, they brought it right up with no issues. The on-property restaurant was amazing (truly delicious), and the front-of-house team was warm and on point the whole time. Overall, I don’t have a single complaint. they are doing an incredible job with customer service. Kudos to the entire team. Reviewed on Nov 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-20/2025-12-26/?FromAirport=YTO&Destination=NYC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=73530346&paandie=true&dealMarker=FFryi8t4rGa7LZ2iP0NlLFyr1Q9YOJxpbfIC2JLQxboSQ139Ed4TnDu7r6L0WizT) ![Kimpton Theta New York - Times Square by IHG](https://images.trvl-media.com/lodging/1000000/20000/16000/15987/c970356b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Theta New York - Times Square by IHG Manhattan CA $1,715 per person Dec 30 - Jan 4 found 22 hours ago Roundtrip flight included Toronto (YTO) to New York (NYC) 17.6/10 Exceptional! (1,265 reviews) Room was fine. The wall decor was a bit strange and the bed was pretty hard. The staff was decently pleasant and helpful and the blow dryer was way better than the small ones some hotels leave ya. No major complaints. Reviewed on Nov 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-30/2026-01-04/?FromAirport=YTO&Destination=NYC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=15987&paandie=true&dealMarker=DIiod8PsM7LKk0CAC5KnoeRXK3Ivoeapz7_T70ahnRRiIEEk2VfjLNymh20LtlKy) ![Fouquet's New York](https://images.trvl-media.com/lodging/89000000/88280000/88270900/88270883/aba7521d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fouquet's New York Manhattan CA $1,862 per person Feb 13 - Feb 16 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (NYC) 19.2/10 Exceptional! (60 reviews) Lovely staff. Incredible property. The hype is real. This is by far and away the nicest property we’ve stayed at in Manhattan in a long time. Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-13/2026-02-16/?FromAirport=YHM&Destination=NYC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=88270883&paandie=true&dealMarker=_Tm_7KZNWR3Ev-ebJ8VodB8fegy9C0oQReT9YofbegMa7eW7FdqX0dh-K6uxkFWt) ## 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! (84 reviews) Overall the places is nice, clean and great views Reviewed on Oct 21, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=04%2F12%2F2025&endDate=05%2F12%2F2025&selected=6473437&PinnedHotelID=6473437&HadPinnedHotel=true®ionId=183716) [](https://expedia.ca/Hotel-Search?startDate=04%2F12%2F2025&endDate=05%2F12%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=04%2F12%2F2025&endDate=05%2F12%2F2025&selected=67569836&PinnedHotelID=67569836&HadPinnedHotel=true®ionId=183716) [](https://expedia.ca/Hotel-Search?startDate=04%2F12%2F2025&endDate=05%2F12%2F2025&selected=67569836&PinnedHotelID=67569836&HadPinnedHotel=true®ionId=183716) ![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 8.2/10 Very Good! (57 reviews) Great Shelter Island Hotel One staff member was there to check us in. He was helpful in bringing our bags to our room. He also suggested several restaurants for us to try. Reviewed on Oct 24, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=04%2F12%2F2025&endDate=05%2F12%2F2025&selected=14997595&PinnedHotelID=14997595&HadPinnedHotel=true®ionId=183716) [](https://expedia.ca/Hotel-Search?startDate=04%2F12%2F2025&endDate=05%2F12%2F2025&selected=14997595&PinnedHotelID=14997595&HadPinnedHotel=true®ionId=183716) [See all 4,719 properties in Shelter Island Heights](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=21%2F11%2F2025&endDate=22%2F11%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 $250 per adult **76%** of travellers recommend [](https://expedia.ca/things-to-do/the-hamptons.a330552.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 - Lodging - Flights - Packages - Cars - Vacation Rental - Other ### Lodging - [3 Star Hotels in Greenport](https://www.expedia.ca/3Star-Greenport-Hotels.s30-0-d110728.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Greenport](https://www.expedia.ca/5Star-Greenport-Hotels.s50-0-d110728.Travel-Guide-Filter-Hotels) - [Coecles Harbor Hotels](https://www.expedia.ca/Coecles-Harbor-Shelter-Island-Hotels.0-n553248635976480820-0.Travel-Guide-Filter-Hotels) - [Hotels near Crescent Beach](https://www.expedia.ca/Crescent-Beach-Hotels.0-l553248621554204758-0.Travel-Guide-Filter-Hotels) - [Cottages in Dering Harbor](https://www.expedia.ca/Dering-Harbor-Cottages.d553248634998885605-aaCottages.Travel-Guide-Accommodation) - [Dering Harbor Hotels](https://www.expedia.ca/Dering-Harbor-Hotels.d553248634998885605.Travel-Guide-Hotels) - [Residences in Dering Harbor](https://www.expedia.ca/Dering-Harbor-Residences.d553248634998885605-aaResidences.Travel-Guide-Accommodation) - [Farmstay in East Marion](https://www.expedia.ca/East-Marion-Agritourism.d6069914-aaAgritourism.Travel-Guide-Accommodation) - [Cabin Rentals in East Marion](https://www.expedia.ca/East-Marion-Cabins.d6069914-aaCabins.Travel-Guide-Accommodation) - [Hotels with Bar in East Marion](https://www.expedia.ca/East-Marion-Hotels-Hotels-With-Bar.0-0-d6069914-tHotelswithBar.Travel-Guide-Filter-Hotels) - [East Marion Hotels](https://www.expedia.ca/East-Marion-Hotels.d6069914.Travel-Guide-Hotels) - [B&B in Greenport](https://www.expedia.ca/Greenport-Bed-And-Breakfast.d110728-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Greenport](https://www.expedia.ca/Greenport-Cabins.d110728-aaCabins.Travel-Guide-Accommodation) - [Adults Only Resorts & in Greenport](https://www.expedia.ca/Greenport-Hotels-Adults-Only-Resorts.0-0-d110728-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Beach-Hotel.0-0-d110728-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Boutique-Hotel.0-0-d110728-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Cheap-Hotels.0-0-d110728-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Greenport](https://www.expedia.ca/Greenport-Hotels-Couples-Resorts-Hotels.0-0-d110728-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Lake Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Lake-Hotels.0-0-d110728-tLakeHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Luxury-Hotel.0-0-d110728-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Oceanfront-Hotels.0-0-d110728-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Shopping-Hotel.0-0-d110728-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Spa-Hotel.0-0-d110728-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Waterpark-Hotels.0-0-d110728-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Greenport Hotels](https://www.expedia.ca/Greenport-Hotels.d110728.Travel-Guide-Hotels) - [Motels in Greenport](https://www.expedia.ca/Greenport-Motels.d110728-aaMotels.Travel-Guide-Accommodation) - [Hotels near Greenport Station](https://www.expedia.ca/Greenport-Station-Hotels.d6186190.Travel-Guide-Hotels) - [Beach Hotel Hotels in Greenport West](https://www.expedia.ca/Greenport-West-Hotels-Beach-Hotel.0-0-d553248635975876381-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Greenport West](https://www.expedia.ca/Greenport-West-Hotels-Cheap-Hotels.0-0-d553248635975876381-tCheapHotels.Travel-Guide-Filter-Hotels) - [Greenport West Hotels](https://www.expedia.ca/Greenport-West-Hotels.d553248635975876381.Travel-Guide-Hotels) - [Adults Only Resorts & in Hay Beach](https://www.expedia.ca/Hay-Beach-Shelter-Island-Hotels-Adults-Only-Resorts.0-n553248635976470037-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Casino Hotels in Hay Beach](https://www.expedia.ca/Hay-Beach-Shelter-Island-Hotels-Casino-Hotel.0-n553248635976470037-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [New York Hotels](https://www.expedia.ca/New-York-Hotels.d178293.Travel-Guide-Hotels) - [B&B in Shelter Island](https://www.expedia.ca/Shelter-Island-Bed-And-Breakfast.d157359-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Adults Only Resorts & in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Adults-Only-Resorts.0-0-d157359-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Beach-Hotel.0-0-d157359-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Boutique-Hotel.0-0-d157359-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Cheap-Hotels.0-0-d157359-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Couples-Resorts-Hotels.0-0-d157359-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Family-Hotel.0-0-d157359-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Hotel-With-Pool.0-0-d157359-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Hotels-With-Free-Breakfast.0-0-d157359-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Luxury-Hotel.0-0-d157359-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Oceanfront-Hotels.0-0-d157359-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Shopping-Hotel.0-0-d157359-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Shelter Island Hotels](https://www.expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels) - [Houseboats in Shelter Island](https://www.expedia.ca/Shelter-Island-Houseboats.d157359-aaHouseboats.Travel-Guide-Accommodation) - [Resorts in Shelter Island](https://www.expedia.ca/Shelter-Island-Resort-Hotels.d157359-aaResortHotels.Travel-Guide-Accommodation) - [Adults Only Resorts & in Silver Beach](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels-Adults-Only-Resorts.0-n553248635976481903-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Silver Beach Hotels](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels.0-n553248635976481903-0.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Southold](https://www.expedia.ca/Southold-Hotels-Romantic-Hotel.0-0-d183719-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Southold Hotels](https://www.expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels) - [Motels in Southold](https://www.expedia.ca/Southold-Motels.d183719-aaMotels.Travel-Guide-Accommodation) - [Hotels near Sunset Beach](https://www.expedia.ca/Sunset-Beach-Hotels.0-l553248626388141313-0.Travel-Guide-Filter-Hotels) - [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. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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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)