Title: Shelter Island Cottages from CA $438 | Expedia.ca [Shelter Island Travel Guide](https://expedia.ca/Shelter-Island.dx157359)[Hotels in Shelter Island](https://expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island](https://expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)[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 Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.ca/Shelter-Island.d157359.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shelter Island cottages ![Smart TV](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/0a5356ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/f28083b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/765aa668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/b72c2ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seabreeze #3: Cozy Cottage by the beach [](https://www.expedia.ca/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information) Hampton Bays 10/10 Exceptional (1 review) CA $77 CA $633 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/c0b20841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/f3aa91d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/185a0230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/0bbae525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk [](https://www.expedia.ca/Waterford-Hotels-Cozy-Renovated-Cottage-With-Game-Room.h108765994.Hotel-Information) Waterford 10/10 Exceptional (15 reviews) "Cottage was perfect. Immaculate, well equipped, beautifully decorated. It had everything we needed! My family and I loved our stay here and will definitely be back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nina B. CA $200 CA $438 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Waterford-Hotels-Cozy-Renovated-Cottage-With-Game-Room.h108765994.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/65eed284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/8e3d5f6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/b4ee006e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/2e009ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1-bedroom cottage with Grove Beach 🏖️ access. [](https://www.expedia.ca/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information) Clinton 9.6/10 Exceptional (34 reviews) "Many local restaurants near by. Christy's for breakfast was very good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin H. CA $109 CA $248 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/5ba709f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/a5732811.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/49ec459f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/94e03953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Cottage, private beach and pass [](https://www.expedia.ca/Niantic-Hotels-Quaint-Beach-Cottage.h105355576.Hotel-Information) East Lyme 10/10 Exceptional (9 reviews) "It was PERFECT way to spend USCGA Parent’s Weekend!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerri G. CA $236 CA $553 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Niantic-Hotels-Quaint-Beach-Cottage.h105355576.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/65eee158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/9e4cf8a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/777d29d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/c4ddd562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town [](https://www.expedia.ca/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information) Greenport 10/10 Exceptional (1 review) "Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeannette M. CA $410 CA $850 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/e52f4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/825be1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/433807ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/1bd85de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Driftwood Cottage @ Saybrook Point Marina, 2 King Beds [](https://www.expedia.ca/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.Hotel-Information) Old Saybrook Center 9.6/10 Exceptional (42 reviews) "Great property, would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) charles b. CA $371 CA $746 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/115000000/114540000/114532600/114532580/503155ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114540000/114532600/114532580/5e492d71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/115000000/114540000/114532600/114532580/3a21009d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114540000/114532600/114532580/f8803a82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seabreeze #4: Charming Cottage Footsteps to the Beach [](https://www.expedia.ca/Hampton-Bays-Hotels-Cozy-Beach-Cottage-Steps-To-Meschutt-Beach.h114532580.Hotel-Information) Hampton Bays 8.8/10 Excellent (3 reviews) "Great stay. Would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Weston B. CA $76 CA $632 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Hampton-Bays-Hotels-Cozy-Beach-Cottage-Steps-To-Meschutt-Beach.h114532580.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-31&endDate=2026-02-01®ionId=157359&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=COTTAGE) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=APART_HOTEL) Condos [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=CONDO) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=APARTMENT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=VILLA) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=HOUSE_BOAT) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Cottages.d157359-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Cottages.d157359-aaCottages.Travel-Guide-Accommodation) ## Top Shelter Island Hotel Reviews ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "Great room and staff" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 10/10 Excellent "The staff was wonderful and the room and views fantastic." [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg) ### Gurney's Montauk Resort & Seawater Spa 10/10 Excellent "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 ! " [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Staff was very friendly room was clean and comfortable " [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "Perfect ❤️" [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Amazing room and view from the room was perfect! " [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Hamlet Inn](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38_y.jpg) ### Hamlet Inn 10/10 Excellent "Nice getaway spot in Southampton. Friendly staff. Well situated to may local points of interest. " [](https://expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Hyatt Place Long Island East End](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb_y.jpg) ### Hyatt Place Long Island East End 10/10 Excellent "Clean and quiet. " [](https://expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) ![Offshore Montauk](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d_y.jpg) ### Offshore Montauk 10/10 Excellent "Always a great stay" [](https://expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ## Find out more about Shelter Island ## Shelter Island Cottages information | Number of reviews | 70 | | ----------------- | ------------ | | Accommodation | 204 Cottages | | Lowest Price | CA $438 | | Highest Price | CA $850 | ## Frequently asked questions ### Why book your cottage in Shelter Island with Expedia? ### How can I find cheap cottages in Shelter Island? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [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) - [Bay Point Hotels ](https://www.expedia.ca/Bay-Point-Sag-Harbor-Hotels.0-n553248635976471151-0.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) - [Town of Southold Town Hotels ](https://www.expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Hotel-Destinations) - [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 Fishers Island ](https://www.expedia.ca/Fishers-Island-Bed-And-Breakfast.d1208-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Fishers Island ](https://www.expedia.ca/Fishers-Island-Guest-Houses.d1208-aaGuestHouses.Travel-Guide-Accommodation) - [Inns in Fishers Island ](https://www.expedia.ca/Fishers-Island-Inns.d1208-aaInns.Travel-Guide-Accommodation) - [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) - [Chalets in North Haven ](https://www.expedia.ca/North-Haven-Chalets.d553248634998589872-aaChalets.Travel-Guide-Accommodation) - [North Haven Hotels ](https://www.expedia.ca/North-Haven-Hotels.d553248634998589872.Travel-Guide-Hotels) - [Residences in North Haven ](https://www.expedia.ca/North-Haven-Residences.d553248634998589872-aaResidences.Travel-Guide-Accommodation) - [B&B in Noyack ](https://www.expedia.ca/Noyack-Bed-And-Breakfast.d6217344-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Noyack ](https://www.expedia.ca/Noyack-Guest-Houses.d6217344-aaGuestHouses.Travel-Guide-Accommodation) - [Noyack Hotels ](https://www.expedia.ca/Noyack-Hotels.d6217344.Travel-Guide-Hotels) - [Aparthotels in Orient ](https://www.expedia.ca/Orient-Apart-Hotels.d6326191-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Orient ](https://www.expedia.ca/Orient-Bed-And-Breakfast.d6326191-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Luxury Hotels in Orient ](https://www.expedia.ca/Orient-Hotels-Luxury-Hotel.0-0-d6326191-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Orient Hotels ](https://www.expedia.ca/Orient-Hotels.d6326191.Travel-Guide-Hotels) - [Inns in Orient ](https://www.expedia.ca/Orient-Inns.d6326191-aaInns.Travel-Guide-Accommodation) - [Resorts in Orient ](https://www.expedia.ca/Orient-Resort-Hotels.d6326191-aaResortHotels.Travel-Guide-Accommodation) - [Aparthotels in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Apart-Hotels.d154327-aaApartHotels.Travel-Guide-Accommodation) - [Apartments in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Apartments.d154327-aaApartments.Travel-Guide-Accommodation) - [B&B in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Bed-And-Breakfast.d154327-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Resorts in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Condominium-Resort.d154327-aaCondominiumResort.Travel-Guide-Accommodation) - [Condo Rentals in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Condos.d154327-aaCondos.Travel-Guide-Accommodation) - [Cottages in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Cottages.d154327-aaCottages.Travel-Guide-Accommodation) - [Guest Houses in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Guest-Houses.d154327-aaGuestHouses.Travel-Guide-Accommodation) - [Sag Harbor Hotels ](https://www.expedia.ca/Sag-Harbor-Hotels.d154327.Travel-Guide-Hotels) - [Inns in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Inns.d154327-aaInns.Travel-Guide-Accommodation) - [Hotels near Sag Harbor Marine Park ](https://www.expedia.ca/Sag-Harbor-Marine-Park-Hotels.0-l6327316-0.Travel-Guide-Filter-Hotels) - [Motels in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Motels.d154327-aaMotels.Travel-Guide-Accommodation) - [Palaces in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Palaces.d154327-aaPalaces.Travel-Guide-Accommodation) - [Vacation Homes in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Private-Vacation-Homes.d154327-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Townhomes in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Townhomes.d154327-aaTownhomes.Travel-Guide-Accommodation) - [B&B in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Bed-And-Breakfast.d183716-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Beach-Hotel.0-0-d183716-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Boutique-Hotel.0-0-d183716-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Couples-Resorts-Hotels.0-0-d183716-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Pet-Friendly-Hotel.0-0-d183716-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Spa-Hotel.0-0-d183716-tSpaHotel.Travel-Guide-Filter-Hotels) - [Shelter Island Heights Hotels ](https://www.expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels) - [Resorts in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Resort-Hotels.d183716-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) - [Cheap Hotels in Southold ](https://www.expedia.ca/Southold-Hotels-Cheap-Hotels.0-0-d183719-tCheapHotels.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 to Greenport ](https://www.expedia.ca/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights) - [Flights from Southold ](https://www.expedia.ca/lp/flights/183719/flights-from-southold) - [Flights from North Haven ](https://www.expedia.ca/lp/flights/553248634998589872/flights-from-north-haven) - [Flights from East Marion ](https://www.expedia.ca/lp/flights/6069914/flights-from-east-marion) - [Flights from Orient ](https://www.expedia.ca/lp/flights/6326191/flights-from-orient) - [Flights from Toronto (YYZ) to New York (NYC) ](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york) - [Visit East Marion ](https://www.expedia.ca/East-Marion.dx6069914) - [Visit Pipes Cove ](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295) - [Kontokosta Winery ](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction) - [Visit North Haven ](https://www.expedia.ca/North-Haven.dx553248634998589872) - [Orient Vacations ](https://www.expedia.ca/Orient.d6326191.Destination-Travel-Guides) - [Visit Bay Point ](https://www.expedia.ca/Sag-Harbor-Bay-Point.dx553248635976471151) - [Visit Sag Harbor ](https://www.expedia.ca/Sag-Harbor.dx154327) - [Shelter Island Heights Vacations ](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides) - [Car rental Greenport ](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide) - [Car rental Orient ](https://www.expedia.ca/Car-Rentals-In-Orient.d6326191.Car-Rental-Guide) - [Things to do in Greenport ](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities) - [Things to do in Sag Harbor ](https://www.expedia.ca/Things-To-Do-In-Sag-Harbor.d154327.Travel-Guide-Activities) - [Things to do in Shelter Island Heights ](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities) - [Book Cottages in Shelter Island on Expedia.com ](https://www.expedia.com/Shelter-Island-Cottages.d157359-aaCottages.Travel-Guide-Accommodation)