Title: Southold Condo Rentals from CA $2,866 | 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 Condos Rentals in Southold from CA $2,866 - ![](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 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=183719&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) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=183719&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 three months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Southold Condo Rentals ![Front of property](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/5689ac07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/ef1a1d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/934c8d81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/253d38d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Hampton Bays 10/10 Exceptional (1) CA $2,367 CA $2,866 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Waterfront-Residences.h109662697.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=2025-12-18&endDate=2025-12-19®ionId=183719&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%2FSouthold-Condos.d183719-aaCondos.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Condos.d183719-aaCondos.Travel-Guide-Accommodation) ## Top Southold Hotel Reviews ![The Sagaponack](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg) ### The Sagaponack 10/10 Excellent "Clean & amenities, staff friendly Thank you " [](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) ![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg) ### Madison Beach Hotel 10/10 Excellent "The Spa was wonderful and the staff was attentive and helpful. " [](https://expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![Hilton Garden Inn Riverhead](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/82ff92d7_y.jpg) ### Hilton Garden Inn Riverhead 10/10 Excellent "Staff was courteous and the room was spotless. Food service is very good as well. " [](https://expedia.ca/Riverhead-Hotels-Hilton-Garden-Inn-Riverhead.h1962521.Hotel-Information) ![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 "A welcoming place with some nice touches." [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.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 "Clean and quiet." [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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 "Our room had a great view of the river and marina. we also loved the seating area in the room. Very comfortable" [](https://expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.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" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![Hotel Indigo East End by IHG](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/75016698_y.jpg) ### Hotel Indigo East End by IHG 10/10 Excellent "Good location, food restaurant. " [](https://expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.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 "The pool was very clean. " [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ## Find out more about Southold ## Southold Condo Rentals information | Number of reviews | 1 | | ----------------- | ---------------- | | Accommodation | 16 Condo Rentals | | Lowest Price | CA $2,866 | | Highest Price | CA $2,866 | ## 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) - [Hotels with Bar in Cutchogue ](https://www.expedia.ca/Cutchogue-Hotels-Hotels-With-Bar.0-0-d183659-tHotelswithBar.Travel-Guide-Filter-Hotels) - 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