Title: Town of Southold Town Vacation Home Rentals from CA $427: Search Top Private Vacation Homes for Rent | 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) # Town of Southold Town Vacation Rentals ## Compare and save ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=VACATION_HOME&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-Private-Vacation-Homes.d110728-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Southold [](https://expedia.ca/Southold-Private-Vacation-Homes.d183719-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/dff376d916af97d7b1d400e631f0d46e.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Cutchogue [](https://expedia.ca/Cutchogue-Private-Vacation-Homes.d183659-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/b87fd2222bd9c0b45cd653e0605bfed5.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Mattituck [](https://expedia.ca/Mattituck-Private-Vacation-Homes.d6223780-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/1/d3e06c642f947ddad6aebc58401dad70.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Orient [](https://expedia.ca/Orient-Private-Vacation-Homes.d6326191-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/c1e146be96c448a68862ae5f1f0cc1a9.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Peconic [](https://expedia.ca/Peconic-Private-Vacation-Homes.d144477-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Featured Vacation Homes in Town of Southold Town ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/9eada5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/eacb8d25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/w906h683x59y0-bf9a7a90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/f66524c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The SandPiper Pipes Cove 9.8/10 Exceptional (27) "My wife and I stayed at the Sandpiper for a long weekend. The property was very clean with a warm welcoming feeling. It is within walking distance to the beach and downtown shopping. Great location. I would recommend it to everyone." [](https://www.expedia.ca/Greenport-Hotels-The-SandPiper.h89698318.Hotel-Information) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/114000000/113960000/113952500/113952436/515b6bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113960000/113952500/113952436/0c15ee88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113960000/113952500/113952436/0f47ab51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/114000000/113960000/113952500/113952436/658af1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea Breeze Paradise: Beachfront & Panoramic Views North Fork 9.8/10 Exceptional (6) "Everything was perfect, very comfortable and the location was outstanding." [](https://www.expedia.ca/Southold-Hotels-Sea-Breeze-Paradise-Beachfront-Panoramic-Views.h113952436.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/104000000/103500000/103495400/103495325/05711c25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103500000/103495400/103495325/4b3e9229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103500000/103495400/103495325/34379718.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103500000/103495400/103495325/3fb5b56b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### I’ve had the best guests! Southold 10/10 Exceptional (26) "House was beautiful - clean -perfect to hang in - pool was great, very private and relaxing - host was hospitable, friendly and accommodating - can’t wait yo go back in the fall!" [](https://www.expedia.ca/Southold-Hotels-Enjoy-The-North-Fork-Of-Long-Island-At-Our-Lovely-Home.h103495325.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/91dd1778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/6f8236be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/35ce389c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/dd4148b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aqua Vista Pipes Cove 10/10 Exceptional (20) "Apartment was great for 2 couples and a baby. The location was amazing, 5 min walk to everything! Beds were super comfy!" [](https://www.expedia.ca/Greenport-Hotels-Aqua-Vista.h89698360.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0195b6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/18f698b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/e69dbcaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/9e0f05a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - Petite King Room 7 Greenport 9.0/10 Wonderful (4) "Great job " CA $277 CA $427 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78740000/78739600/78739514/ad04b844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78740000/78739600/78739514/53e3b6de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78740000/78739600/78739514/00a337a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78740000/78739600/78739514/ba983a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Water front beach house w/ private beach with 3 bedrooms/2 bathrooms/Large Deck Greenport 9.4/10 Exceptional (8) "Overall great experience. Relaxing and quiet escape." [](https://www.expedia.ca/Greenport-Hotels-Water-Front-Beach-House-W-Private-Beach.h78739514.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117640000/117633600/117633587/443b6345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/118000000/117640000/117633600/117633587/61066f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117640000/117633600/117633587/f2e81c19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/118000000/117640000/117633600/117633587/356a90a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Constructed 3-bedroom Modern Farmhouse - walk to Greenport Village! Greenport 10/10 Exceptional (1) "Beautiful newly renovated home, walking distance to Greenport harbor. Very accommodating to families with small children. Great backyard and playground around the corner. Will stay again! " [](https://www.expedia.ca/Greenport-Hotels-Newly-Constructed-3-Bedroom-Modern-Farmhouse-Walk-To-Greenport-Village.h117633587.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33980000/33974300/33974244/41edf25f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33980000/33974300/33974244/d6a2fef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33980000/33974300/33974244/w750h526x0y404-a5e5a746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33980000/33974300/33974244/38b054f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Luxury Seaside Getaway New Suffolk 10/10 Exceptional (35) "great location, house was a great fit for 6 adults and 3 children under 5 years old, pool area and pool wonderful, property managers wonderful to work with, responsive, nice and professional." [](https://www.expedia.ca/New-Suffolk-Hotels-Historic-Luxury-Seaside-Getaway.h33974244.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/119000000/118740000/118737900/118737819/854c1d63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/119000000/118740000/118737900/118737819/9b7457df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/119000000/118740000/118737900/118737819/199644f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118740000/118737900/118737819/0ce78844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,... Peconic [](https://www.expedia.ca/Peconic-Hotels-Newly-Renovated.h118737819.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/22b35fec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/115e86e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/118c8886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/2cdaf891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Farmhouse Steps to Beach and Love Lane Mattituck 10/10 Exceptional (37) "A nice and cozy place to retreat from the city for awhile, loved it!" [](https://www.expedia.ca/Mattituck-Hotels-Modern-Cottage-In-Northfork-Steps-From-Love-Lane-And-Veterans-Beach.h73728881.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/35000000/34280000/34279500/34279494/bf4fe8ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34280000/34279500/34279494/2272a78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach towels](https://images.trvl-media.com/lodging/35000000/34280000/34279500/34279494/9dd7676b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34280000/34279500/34279494/8a05d089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Historical 6 bdrm House close to vineyards and breweries, Peconic 10/10 Exceptional (33) "Property is centrally located in beautiful Peconic, very unique home on a great plot of land. Would definitely stay here again." [](https://www.expedia.ca/Peconic-Hotels-Gorgeous-Historical-6-Bdrm-House-Close-To-Vineyards-And-Breweries.h34279494.Hotel-Information) ![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/35000000/34090000/34087000/34086902/w1439h959x1y1-90363051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34090000/34087000/34086902/w1439h959x1y1-bdb6da8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34090000/34087000/34086902/be65b622.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/35000000/34090000/34087000/34086902/w1383h959x0y1-1366fb3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Beachfront Home ~ 5BR/3BA Family Friendly Laurel 10/10 Exceptional (168) "Seamless check in and out. Perfect location. Gorgeous house and view. Safe neighborhood! Had a blast!" [](https://www.expedia.ca/Laurel-Hotels-Spectacular-Beachfront-Contemporary-Wine-Country.h34086902.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/46000000/45700000/45695900/45695860/08465ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/46000000/45700000/45695900/45695860/25d27dd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/46000000/45700000/45695900/45695860/072cf79a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/46000000/45700000/45695900/45695860/3784f711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Beach House, Steps to Beach Mattituck 10/10 Exceptional (20) "Another wonderful stay at this beautiful home in Mattituck. The house has everything you need and the hosts are first rate. The perfect get away." [](https://www.expedia.ca/Mattituck-Hotels-Steps-To-Beach-And-Spectacular-Sunsets.h45695860.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/84000000/83360000/83356300/83356208/00888291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/84000000/83360000/83356300/83356208/w1441h1080x239y0-b2eec2bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/84000000/83360000/83356300/83356208/e1f98cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83360000/83356300/83356208/f26d40a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Respite Ranch Private Pool, Hot Tub, BBQ Grill Mattituck 9.8/10 Exceptional (10) "Great stay and wonderful property. The first stay that didn’t have a book and list full of restrictions and checkout instructions. After a whirlwind weekend celebrating our daughter ‘s engagement, this was a welcomed surprise! Everyone enjoyed their stay, including our two labs. Great fenced in yard that gave them plenty of room to exercise. We will be back!" [](https://www.expedia.ca/Mattituck-Hotels-Respite-Ranch-Private-Pool.h83356208.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78600000/78591900/78591812/w1274h822x5y0-470f2a3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/79000000/78600000/78591900/78591812/37ae560a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78600000/78591900/78591812/047a7c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/79000000/78600000/78591900/78591812/2092e42b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Fork Family and Friends Getaway. Great Location Mattituck 10/10 Exceptional (15) "Great long weekend stay with kids and grandkids while attending a family wedding. Super clean, decorated well, pool and outdoor areas even better than the pictures. Responsive owner. Highly recommended" [](https://www.expedia.ca/Laurel-Hotels-Mattiuck-Retreat.h78591812.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/114000000/113200000/113191700/113191658/c5a4fafa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113200000/113191700/113191658/889960d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113200000/113191700/113191658/2bebc1e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113200000/113191700/113191658/7f435eef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful home short walk to the beach, w/ outdoor shower, grill & central AC East Marion [](https://www.expedia.ca/East-Marion-Hotels-Beautiful-Home-Short-Walk-To-The-Beach.h113191658.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/113000000/112710000/112700700/112700627/d573983a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/113000000/112710000/112700700/112700627/717167a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112710000/112700700/112700627/5fe4bfdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/113000000/112710000/112700700/112700627/0f4016dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families Greenport 10/10 Exceptional (4) "Perfect location and accommodations for our family getaway. The kids loved the pool and the basketball hoop.Overall, the house was very comfortable and well equipped. " [](https://www.expedia.ca/Greenport-Hotels-Spacious-North-Fork-Home-In-Greenport.h112700627.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/57000000/56920000/56911800/56911757/b7d59b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/57000000/56920000/56911800/56911757/8c7cb5e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/57000000/56920000/56911800/56911757/w2048h1536x0y0-1200d322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/57000000/56920000/56911800/56911757/w2048h1536x0y0-2e645f04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries Southold 9.6/10 Exceptional (24) "This property was ideal for us visiting friends in Southold. It's also close to all the vineyards, Greenport and Shelter Island which we visited via ferry en route to Sag Harbour. The property is well equipped for self catering and the deck is lovely overlooking the creek. We had a few issues with the internet on arrival but Jeff kept in touch and sorted the problem. If we visit Southold again we will definitely consider this property as Jeff has plans to update and renovate parts of the... [](https://www.expedia.ca/Southold-Hotels-Heated-Pool-On-Goose-Creek.h56911757.Hotel-Information) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/113000000/112800000/112791900/112791823/17fe4507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, stereo](https://images.trvl-media.com/lodging/113000000/112800000/112791900/112791823/12515a00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112800000/112791900/112791823/6ab4899b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112800000/112791900/112791823/0f528c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mattituck Luxury Estate + Pool + 5 Bedrooms Mattituck [](https://www.expedia.ca/Mattituck-Hotels-Mattituck-Luxury-Estate-Pool-5-Bedrooms.h112791823.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104100000/104090300/104090249/5fb7f429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/105000000/104100000/104090300/104090249/7c1993ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104100000/104090300/104090249/7f164351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/105000000/104100000/104090300/104090249/w1920h956x0y62-75f47c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bahia Mar Beach House, North Fork Laurel 10/10 Exceptional (6) "My favorite stay to date! Just perfection all around!" [](https://www.expedia.ca/Laurel-Hotels-Bahia-Mar-Beach-House.h104090249.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=2025-10-17&endDate=2025-10-18®ionId=553248635976002319&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&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-Private-Vacation-Homes.d553248635976002319-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Southold-Town-Private-Vacation-Homes.d553248635976002319-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Town of Southold Town Hotel Reviews ![Greenporter Hotel](//images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg) ### Greenporter Hotel 10/10 Excellent "Everything was in walking distance. Clean room" [](https://expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.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 "Great quick stay" [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Zey Hotel](//images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg) ### Zey Hotel 10/10 Excellent "Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay." [](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.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 "Quiet, nice, clean, friendly and helpful staff. It would have been nice if they had more avilable apps for streaming tv." [](https://expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information) ![The Harbor Front Inn](//images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 10/10 Excellent "We brought our bikes and the staff was very accommodating and helped us store them each night. We had a great time and will be back!" [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Harbor Heights ](//images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/b0e39c6f_y.jpg) ### Harbor Heights 10/10 Excellent "This was a perfect location and such a cute place! The apartment was spotless and well appointed. " [](https://expedia.ca/Greenport-Hotels-Harbor-Heights.h102716809.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Clean and beautiful view" [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) !['The Gate House'on Beach front Estate with Dockage. Walk to Village .](//images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/89437aaa_y.jpg) ### 'The Gate House'on Beach front Estate with Dockage. Walk to Village . 10/10 Excellent "This was the perfect long weekend getaway. The location is unbeatable. Downtown was just a five minute drive and the beach was just a few steps from our house. Communication with our host was excellent and the house was very clean and exactly as described. We took advantage of the charcoal grill every night. For children, there’s a beautiful waterfront playground nearby, a carousel downtown and a miniature train ride just a few minutes away. While it is described in the listing, I would just note that there are multiple homes on the property (3 or 4, I think). They are well spaced and you do have your privacy but it is worth noting. This didn’t make a difference to my family and I as we are already planning our next return. " [](https://expedia.ca/Greenport-Hotels-The-Gate-Houseon-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34201329.Hotel-Information) ![Vine & Sand](//images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/a9ca389a_y.jpg) ### Vine & Sand 10/10 Excellent "Amazing hospitality, high end linens, conveniently stocked fridge / pantry. Peaceful and relaxing for an anniversary weekend. Rooms are beautiful, location is central to wineries and a gorgeous bay beach. Highly recommend!" [](https://expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information) ## Find out more about Town of Southold Town ## Town of Southold Town Vacation Homes information | Number of reviews | 415 | | --- | --- | | Accommodation | 223 Vacation Homes | | Lowest Price | CA $427 | | Highest Price | CA $427 | ## 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) - 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