Title: Town of Southold Town Apartment Rentals | Expedia.ca [Town of Southold Town Travel Guide](https://expedia.ca/Town-Of-Southold-Town.dx553248635976002319)[Town of Southold Town Hotels](https://expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Hotel-Destinations)[Vacation Rentals in Town of Southold Town](https://expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Vacation-Rental-Destinations)[Town of Southold Town Car Rentals](https://expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Car-Rental-Destinations)[Town of Southold Town Vacations](https://expedia.ca/Town-Of-Southold-Town.d553248635976002319.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Apartment Rentals in Town of Southold Town ## Compare and save ![](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 Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Featured Apartments in Town of Southold Town ![Beach](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/b0e39c6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/c1cf6b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/w2160h1432x0y4-657cfcb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/4bd9bc98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbor Heights Pipes Cove 9.8/10 Exceptional (10) "This was a perfect location and such a cute place! The apartment was spotless and well appointed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela [](https://www.expedia.ca/Greenport-Hotels-Harbor-Heights.h102716809.Hotel-Information) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/95000000/94390000/94380400/94380332/0a6d2241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/95000000/94390000/94380400/94380332/9928bb2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/95000000/94390000/94380400/94380332/6da46bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/95000000/94390000/94380400/94380332/28bfef98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint DT Greenport Apt - 2 Mi to Shelter Island! Greenport 10/10 Exceptional (1) "This was the perfect, in town place to stay for the two of us. Located on a quiet street of well-maintained homes, and with parking right outside, it was a short 1-1/2 block walk to all the shops, restaurants, ferry, docks, etc. The apt is small, but clean and tidy, sun-filled and air-conditioned. We loved staying here and will again in the future." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa [](https://www.expedia.ca/Greenport-Hotels-Quaint-DT-Greenport-Apt-2-Mi-To-Shelter-Island.h94380332.Hotel-Information) ![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956600/94956540/c7c580c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/95000000/94960000/94956600/94956540/0522e8eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956600/94956540/79cfb2db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956600/94956540/14a82d25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Greenport Gem 1, 1 Mile to Ferry! Greenport 10/10 Exceptional (1) "extra clean brand new rooms. bathroom door did lock by itself and the small hole on the plate outside did unlock it when depressed otherwise perfect. we had 2 under 3 kids and the way it was set up was safe and fun" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) susan [](https://www.expedia.ca/Greenport-Hotels-Charming-Greenport-Gem-1.h94956540.Hotel-Information) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94351300/94351256/a4b0b08f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94351300/94351256/52f35f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94351300/94351256/fa0ac669.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94351300/94351256/70dff57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright Apartment - 1/2 Mi to Greenport Harbor! Greenport 10/10 Exceptional (1) "John communicated well with clear directions. His book of local suggestions were helpful and we loved the location - walking/biking distance to all the action! Loved Greenport!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maura [](https://www.expedia.ca/Greenport-Hotels-Bright-2nd-Floor-Apt-12-Mi-To-Greenport-Harbor.h94351256.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33920000/33914000/33913986/5c92d77e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33920000/33914000/33913986/fdb2707c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33920000/33914000/33913986/5429348e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/34000000/33920000/33914000/33913986/c8ef1b38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village. Pipes Cove 10/10 Exceptional (150) "Apartment was clean, spacious for 2 people, and well equipped. Location was perfect with a short walk to a town beach and about a 10-15 minute walk to the LIRR station and into the town of Greenport. Hosts were lovely and responsive. Would definitely recommend and also go back again next summer. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elayne C. [](https://www.expedia.ca/Greenport-Hotels-Private-Spacious-Five-Room-SuiteSteps-To-Bay-Beach-And-Walk-To-Village.h33913986.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/113000000/112800000/112791900/112791809/57da70b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games](https://images.trvl-media.com/lodging/113000000/112800000/112791900/112791809/e1d5b0df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112800000/112791900/112791809/78b3b857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112800000/112791900/112791809/9b8fd94f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peconic Bay Beach House + 5 bedrooms + spacious + Southhold 10/10 Exceptional (13) "Being across from the beach was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan H. [](https://www.expedia.ca/Southold-Hotels-Peconic-Bay-Beach-House-5-Bedrooms-Spacious.h112791809.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/117000000/116090000/116087100/116087051/1c2110e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/117000000/116090000/116087100/116087051/d2cb21e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116090000/116087100/116087051/a304916c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116090000/116087100/116087051/c1594557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Relaxing 2-Bedroom Retreat Minutes from Stunning Beaches and local Wineries!" Laurel [](https://www.expedia.ca/Laurel-Hotels-Relaxing-2-Bedroom-Retreat-Minutes-From-Stunning-Beaches-And-Local-Wineries.h116087051.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87700000/87690700/87690602/w906h683x59y0-c588373b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87700000/87690700/87690602/w905h683x60y0-dd00656f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/88000000/87700000/87690700/87690602/w508h683x258y0-b5ad00a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87700000/87690700/87690602/w905h683x60y0-54a147f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2-bedroom in Heart of Greenport Historic District Greenport [](https://www.expedia.ca/Greenport-Hotels-2-Bedroom-In-Heart-Of-Greenport-Historic-District.h87690602.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/28000000/27180000/27172700/27172629/6055ae2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27180000/27172700/27172629/5d34c7a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27180000/27172700/27172629/0eb3fc90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27180000/27172700/27172629/3cd0875d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect Getaway Apartment For Couples or Single Travelers East Marion 10/10 Exceptional (15) "It was wonderful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah H. [](https://www.expedia.ca/East-Marion-Hotels-Perfect-Getaway-Apartment-For-Couples-Or-Single-Travelers.h27172629.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94690000/94687000/94686912/9233cc8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/95000000/94690000/94687000/94686912/86b44550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94690000/94687000/94686912/a2e74e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94690000/94687000/94686912/01f90cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Guest Room-heart of Long Island's North Fork wine country-steps to beach Southold [](https://www.expedia.ca/Southold-Hotels-Private-Guest-Room-Heart-Of-Long-Islands-North-Fork-Wine-Country-Steps-To-Beach.h94686912.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/97000000/96520000/96516600/96516515/w379h683x323y0-d565ff40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/97000000/96520000/96516600/96516515/w1024h569x0y57-713d9b6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/97000000/96520000/96516600/96516515/w1024h569x0y57-6783517c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms](https://images.trvl-media.com/lodging/97000000/96520000/96516600/96516515/w1024h569x0y57-37cdb53a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greenport Loft Apartment Greenport [](https://www.expedia.ca/Greenport-Hotels-Greenport-Loft-Apartment.h96516515.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/118000000/117680000/117670400/117670316/440c7e23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117680000/117670400/117670316/a680c6cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117680000/117670400/117670316/17a9a10f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117680000/117670400/117670316/fac98505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Over-The-Water 3-Bedroom Loft Apartment Mattituck [](https://www.expedia.ca/Mattituck-Hotels-Historic-Over-The-Water-3-Bedroom-Loft-Apartment.h117670316.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=2025-11-08&endDate=2025-11-09®ionId=553248635976002319&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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%2FTown-Of-Southold-Town-Apartments.d553248635976002319-aaApartments.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Southold-Town-Apartments.d553248635976002319-aaApartments.Travel-Guide-Accommodation) ## Top Town of Southold Town Hotel Reviews ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Breakfast and the Halyard restaurant are top shelf. A few quirks with our room(s) - no cable service, a locked bathroom door that couldn’t be opened, and a dead bolt that didn’t work- but the staff were helpful and accommodating and did everything they could to make things right." [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Zey Hotel](//images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg) ### Zey Hotel 10/10 Excellent "Hotel is centrally located in town. Staff was welcoming and warm. Free parking being the building. Lots of places to relax. " [](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ![Greenporter Hotel](//images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg) ### Greenporter Hotel 10/10 Excellent "Great place. Would come again" [](https://expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ![Surrounded by nature, come stay in this 1 bedroom private, serene location](//images.trvl-media.com/lodging/121000000/120190000/120181100/120181056/1bf16838_y.jpg) ### Surrounded by nature, come stay in this 1 bedroom private, serene location 10/10 Excellent "This apartment is on the lower level of a house, and the house is 10-15 minutes from every place we wanted to be. The bathroom and kitchen are newly renovated, and the very spiffy toaster oven heated up pizza quickly. There is an induction cook top for the more adventurous. I slept very well, but you will contend with about 10 pillows before you can get into bed. (My husband is not a decorative pillow guy). No issues with plumbing, electricity, or heat. Because it was my birthday on Friday, and we were stuck in so much traffic that we had to cancel our dinner reservations, I was really touched to see two small happy birthday cupcakes waiting." [](https://expedia.ca/Southold-Hotels-Surrounded-By-Nature.h120181056.Hotel-Information) ![Vine & Sand](//images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/a9ca389a_y.jpg) ### Vine & Sand 10/10 Excellent "This B&B, and its hosts, were simply amazing. I cannot recommend this place enough." [](https://expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information) ![The Menhaden](//images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf_y.jpg) ### The Menhaden 10/10 Excellent "From the friendly check in with Mario to the check out everything was top class .The private bar is a really special touch and Dan was a great bar tender. The roof top is very nice to relax on with a glass of wine and the fire pit lit. Rooms are comfortable and spotless. There is a galley on each floor where they have coffee water and soda free all day plus fresh croissants in the morning .Highly recommend this hotel " [](https://expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information) ![Silver Sands Motel & Beach Bungalows](//images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/52eefc00_y.jpg) ### Silver Sands Motel & Beach Bungalows 10/10 Excellent "Amazing property" [](https://expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information) ![The Shoals Suites and Slips](//images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg) ### The Shoals Suites and Slips 10/10 Excellent "This property was insanely clean and well kept. Location lovely and close to restaurants wineries and farms to visit. Scenery pretty . Wished they had one more fire pit! " [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Cliffside Resort Condominiums](//images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/1638a16b_y.jpg) ### Cliffside Resort Condominiums 10/10 Excellent "Our unit was clean and neat. Beds and pillows could be upgraded (they were very soft). " [](https://expedia.ca/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information) ## Find out more about Town of Southold Town ## Town of Southold Town Apartments information | Number of reviews | 128 | | --- | --- | | Accommodation | 14 Apartments | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [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) - [Hotels near Crescent Beach](https://www.expedia.ca/Crescent-Beach-Hotels.0-l553248621554204758-0.Travel-Guide-Filter-Hotels) - [Chalets in Cutchogue](https://www.expedia.ca/Cutchogue-Chalets.d183659-aaChalets.Travel-Guide-Accommodation) - [Cutchogue Hotels](https://www.expedia.ca/Cutchogue-Hotels.d183659.Travel-Guide-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) - [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) - [Apartments in Mattituck](https://www.expedia.ca/Mattituck-Apartments.d6223780-aaApartments.Travel-Guide-Accommodation) - [B&B in Mattituck](https://www.expedia.ca/Mattituck-Bed-And-Breakfast.d6223780-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Mattituck](https://www.expedia.ca/Mattituck-Motels.d6223780-aaMotels.Travel-Guide-Accommodation) - [Guest Houses in New Suffolk](https://www.expedia.ca/New-Suffolk-Guest-Houses.d3000449151-aaGuestHouses.Travel-Guide-Accommodation) - [Motels in New Suffolk](https://www.expedia.ca/New-Suffolk-Motels.d3000449151-aaMotels.Travel-Guide-Accommodation) - [Vacation Homes in New Suffolk](https://www.expedia.ca/New-Suffolk-Private-Vacation-Homes.d3000449151-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [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) - [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) - [B&B in Orient](https://www.expedia.ca/Orient-Bed-And-Breakfast.d6326191-aaBedAndBreakfast.Travel-Guide-Accommodation) - [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) - [Beach Hotel Hotels in Peconic](https://www.expedia.ca/Peconic-Hotels-Beach-Hotel.0-0-d144477-tBeachHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Peconic](https://www.expedia.ca/Peconic-Hotels-Ski-Hotel.0-0-d144477-tSkiHotel.Travel-Guide-Filter-Hotels) - [Peconic Hotels](https://www.expedia.ca/Peconic-Hotels.d144477.Travel-Guide-Hotels) - [Motels in Peconic](https://www.expedia.ca/Peconic-Motels.d144477-aaMotels.Travel-Guide-Accommodation) - [Vacation Homes in Peconic](https://www.expedia.ca/Peconic-Private-Vacation-Homes.d144477-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Villas in Peconic](https://www.expedia.ca/Peconic-Villas.d144477-aaVillas.Travel-Guide-Accommodation) - [Hotels near Pindar Vineyards](https://www.expedia.ca/Pindar-Vineyards-Hotels.0-l6326965-0.Travel-Guide-Filter-Hotels) - [B&B in Shelter Island](https://www.expedia.ca/Shelter-Island-Bed-And-Breakfast.d157359-aaBedAndBreakfast.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 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) - [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) - [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 Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york) - [Bedell Cellars](https://www.expedia.ca/Bedell-Cellars-Cutchogue.d553248621532665643.Vacation-Attraction) - [Visit Pipes Cove](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295) - [Pindar Vineyards](https://www.expedia.ca/Pindar-Vineyards-Peconic.d6326965.Vacation-Attraction) - [Shelter Island Heights Vacations](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides) - [Visit Shelter Island](https://www.expedia.ca/Shelter-Island.dx157359) - [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) - [Shelter Island Vacation Rentals](https://www.expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals) - [Things to do in Greenport](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.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) - [Things to do in Shelter Island](https://www.expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)