Title: Southold Houseboats from CA $527 | Expedia.ca [Hotels in Southold](https://expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels)[Vacation Rentals in Southold](https://expedia.ca/Southold-Vacation-Rentals.d183719.Travel-Guide-VacationRentals)[Flights to Southold](https://expedia.ca/Cheap-Flights-To-Southold.d183719.Travel-Guide-Flights)[Southold Car Rentals](https://expedia.ca/Car-Rentals-In-Southold.d183719.Car-Rental-Guide)[Southold Vacation Packages](https://expedia.ca/Southold.d183719.Destination-Travel-Guides) ![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Benny Goh # Search Houseboats in Southold from CA $527 - ![](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 [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Southold Houseboats ![Exterior](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/e3540489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/85d04a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/bebec502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/82b258de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Floating Nest on Private River. Serene Views & Ultimate Relaxation Old Lyme CA $316 CA $527 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Old-Lyme-Hotels-Floating-Nest-On-Private-River-Serene-Views-Ultimate-Relaxation.h103095183.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=2025-12-12&endDate=2025-12-13®ionId=183719&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_183719) ## Find vacation rentals that suit your style Cottages [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=VACATION_HOME) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=CABIN) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=APARTMENT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=VILLA) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&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%2FSouthold-Houseboats.d183719-aaHouseboats.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Houseboats.d183719-aaHouseboats.Travel-Guide-Accommodation) ## Top Southold Hotel Reviews ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "The room was spotless, spacious and unique. Staff was very friendly and efficient. Amenities are what you need. " [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Spark by Hilton Guilford](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2_y.jpg) ### Spark by Hilton Guilford 10/10 Excellent "Kind staff. Easy check-in. Clean rooms and good location. " [](https://expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Great hotel for a quick stay - very friendly staff" [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.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 "Room was clean and comfortable. Easy check in and check out. Staff very accommodating. " [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.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 "Always love staying there when in Greenport. Clean. Central. Quality continental breakfast." [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 10/10 Excellent "Great" [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![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 "Staff is fantastic " [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 10/10 Excellent "EXCELLENT staff ! Room was clean. Will stay again " [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Hamlet Inn](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38_y.jpg) ### Hamlet Inn 10/10 Excellent "Everything is great" [](https://expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ## Find out more about Southold ## Southold Houseboats information | Number of reviews | | | --- | --- | | Accommodation | 3 Houseboats | | Lowest Price | CA $527 | | Highest Price | CA $527 | ## 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) - 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[Silver Beach Hotels](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels.0-n553248635976481903-0.Travel-Guide-Filter-Hotels) - [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 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) - [Kontokosta Winery](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction) - [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) - [Book Houseboats in Southold on Expedia.com](https://www.expedia.com/Southold-Houseboats.d183719-aaHouseboats.Travel-Guide-Accommodation)