Title: Town of Southold Town Condominium Resort Rental | 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) ![Lavender farm on Long Island ](https://images.trvl-media.com/place/6069914/ada6e93d-1aa6-4a8f-b17b-ce0cc0fcdf57.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by gavvykins ![](https://images.trvl-media.com/place/6069914/ada6e93d-1aa6-4a8f-b17b-ce0cc0fcdf57.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 [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&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 two months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Town of Southold Town ![](https://mediaim.expedia.com/destination/2/9a9f855657c0f02d64549df7b59e54eb.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Greenport [](https://expedia.ca/Greenport-Condominium-Resort.d110728-aaCondominiumResort.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Southold [](https://expedia.ca/Southold-Condominium-Resort.d183719-aaCondominiumResort.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/b87fd2222bd9c0b45cd653e0605bfed5.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Mattituck [](https://expedia.ca/Mattituck-Condominium-Resort.d6223780-aaCondominiumResort.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/1/d3e06c642f947ddad6aebc58401dad70.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Orient [](https://expedia.ca/Orient-Condominium-Resort.d6326191-aaCondominiumResort.Travel-Guide-Accommodation) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. 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[Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_553248635976002319) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=APART_HOTEL) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VACATION_HOME) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VILLA) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=COTTAGE) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CABIN) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&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%2FTown-Of-Southold-Town-Condominium-Resort.d553248635976002319-aaCondominiumResort.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Southold-Town-Condominium-Resort.d553248635976002319-aaCondominiumResort.Travel-Guide-Accommodation) ## Top Town of Southold Town Hotel Reviews ![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 10/10 Excellent "Fantastic stay. Excellent service. Perfect location. Wonderful breakfast." [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg) ### The Shoals Suites and Slips 10/10 Excellent "Clean and spacious room" [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Zey Hotel](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg) ### Zey Hotel 10/10 Excellent "Other guests mentioned that it was noisy, we heard nothing. Rooms are small, but perfect for a get away. Staff was helpful, kind, and courteous. Had a really nice stay." [](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ![American Beech Hotel](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/0caf92d6_y.jpg) ### American Beech Hotel 10/10 Excellent "Very nice and very clean." [](https://expedia.ca/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information) ![Cottage on Beach front Estate with Dockage .Walk to Village](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/eb9640ef_y.jpg) ### Cottage on Beach front Estate with Dockage .Walk to Village 10/10 Excellent "Pat was great, picked me up from the train station and brought me to the grocery store to grab some supplies. Place was cozy and super quiet/peaceful. I was here in January so I'd love to come back in the summer and enjoy the beach, which is right on the property." [](https://expedia.ca/Greenport-Hotels-Cottage-On-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34381035.Hotel-Information) ![The SandPiper ](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/9eada5e0_y.jpg) ### The SandPiper 10/10 Excellent "The host was very understanding about some last minute events that affected our trip" [](https://expedia.ca/Greenport-Hotels-The-SandPiper.h89698318.Hotel-Information) ![Vine & Sand](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/a9ca389a_y.jpg) ### Vine & Sand 10/10 Excellent "Vine + Sand was wonderful. The hosts were so friendly and it was close to many wineries." [](https://expedia.ca/Southold-Hotels-Vine-Sand.h96718085.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) ![The Menhaden](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf_y.jpg) ### The Menhaden 10/10 Excellent "Loved our stay at the Menhaden! Everything was great especially the staff who went beyond our expectations...from offering us champagne and my husband a great mocktail to cleaning the snow off our car! The place is so pretty and the bar has all fun games & all albums you can play. The king room was large, no bath though :( and it was a bit cold in there, they did try and fix it though. Breakfast and goodies available all day on our floor with sodas, water, coffee and cappuccinos :). " [](https://expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information) ## Find out more about Town of Southold Town ## Town of Southold Town Condo Resorts information | Number of reviews | | | ----------------- | ------------- | | Accommodation | Condo Resorts | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - 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) - [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) - 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