Title: Town of Southold Town Cottages from CA $819 | 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 [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&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) In three months [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-05-15&endDate=2026-05-17&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-Cottages.d110728-aaCottages.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/dff376d916af97d7b1d400e631f0d46e.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Cutchogue [](https://expedia.ca/Cutchogue-Cottages.d183659-aaCottages.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Southold [](https://expedia.ca/Southold-Cottages.d183719-aaCottages.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/b87fd2222bd9c0b45cd653e0605bfed5.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Mattituck [](https://expedia.ca/Mattituck-Cottages.d6223780-aaCottages.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/1/d3e06c642f947ddad6aebc58401dad70.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Orient [](https://expedia.ca/Orient-Cottages.d6326191-aaCottages.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/c1e146be96c448a68862ae5f1f0cc1a9.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Peconic [](https://expedia.ca/Peconic-Cottages.d144477-aaCottages.Travel-Guide-Accommodation) ## Our top choices for Town of Southold Town cottages ![Cottage, 2 Bedrooms, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/f0c0c2c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property map](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/b50e5baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Tent, 1 Queen Bed](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/fe9ed1d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 2 Bedrooms, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/e632266d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Fork Cottages & RV Resort [](https://www.expedia.ca/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information) Greenport 9.2/10 Wonderful (10 reviews) "great place to stay, clean and quiet....loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darlin [](https://www.expedia.ca/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/b9021a3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/70fef5cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/dcee1147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/077d4275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 'The Gate House'on Beach front Estate with Dockage. Walk to Village . [](https://www.expedia.ca/Greenport-Hotels-The-Gate-Houseon-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34201329.Hotel-Information) Pipes Cove 9.8/10 Exceptional (102 reviews) "Relaxing stay on beautiful property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Annie B. [](https://www.expedia.ca/Greenport-Hotels-The-Gate-Houseon-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34201329.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83420000/83412200/83412176/a97bb723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83420000/83412200/83412176/31e4db08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83420000/83412200/83412176/3201018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83420000/83412200/83412176/b285b845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Totally Renovated Cottage on the North Fork 7 min. walk to the Beach [](https://www.expedia.ca/Cutchogue-Hotels-Totally-Renovated-Cottage-On-The-North-Fork-7-Min-Walk-To-The-Beach.h83412176.Hotel-Information) Cutchogue 10/10 Exceptional (28 reviews) "We had an amazing stay at this home. The house was exactly as described and was plenty of space for a family of 4 to spend a weekend. We particularly enjoyed the porch and large back yard as well as the proximity to beaches, wineries, and dining. The owner was extremely responsive throughout our stay and made us feel very welcome. Would highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathryn P. [](https://www.expedia.ca/Cutchogue-Hotels-Totally-Renovated-Cottage-On-The-North-Fork-7-Min-Walk-To-The-Beach.h83412176.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/33000000/32630000/32625000/32624902/78f0be45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/33000000/32630000/32625000/32624902/b7f92081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers](https://images.trvl-media.com/lodging/33000000/32630000/32625000/32624902/cbe1e5ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32630000/32625000/32624902/129c803e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely Cottage in the Heart of Long Island Wine country [](https://www.expedia.ca/Southold-Hotels-Lovely-Waterview-Cottage-In-The-Heart-Of-Long-Island-Wine-Country.h32624902.Hotel-Information) Southold 9.8/10 Exceptional (30 reviews) "Perfect for what I needed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike H. [](https://www.expedia.ca/Southold-Hotels-Lovely-Waterview-Cottage-In-The-Heart-Of-Long-Island-Wine-Country.h32624902.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33504800/33504750/49305000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33510000/33504800/33504750/87aa90b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/34000000/33510000/33504800/33504750/w799h599x1y1-81068992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33504800/33504750/w796h599x1y1-98f67757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fabulous Waterfront Property in the Heart of Wine Country [](https://www.expedia.ca/Peconic-Hotels-Fabulous-Waterfront-Property-In-The-Heart-Of-Wine-Country.h33504750.Hotel-Information) Peconic 10/10 Exceptional (184 reviews) "Great place and beautiful scenery" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Normand H. [](https://www.expedia.ca/Peconic-Hotels-Fabulous-Waterfront-Property-In-The-Heart-Of-Wine-Country.h33504750.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94345100/94345066/13d84275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94345100/94345066/f11346b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94345100/94345066/26da66af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94345100/94345066/c5cfac5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Beach: Long Island Wine Country Home! [](https://www.expedia.ca/Cutchogue-Hotels-Home-In-Long-Island-Wine-Country-Walk-To-Beach.h94345066.Hotel-Information) Cutchogue [](https://www.expedia.ca/Cutchogue-Hotels-Home-In-Long-Island-Wine-Country-Walk-To-Beach.h94345066.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92180000/92173200/92173172/38f1b429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92180000/92173200/92173172/59606321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92180000/92173200/92173172/c6a87d69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92180000/92173200/92173172/ebae7ba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations! [](https://www.expedia.ca/Mattituck-Hotels-Renovated-2-Bedroom-Guest-Cottage-Minutes-To-Beach-And-All-North-Fork-Activities.h92173172.Hotel-Information) Mattituck 10/10 Exceptional (13 reviews) "The host was amazing and super responsive. Great location and very easy check-in/checkout. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian K. [](https://www.expedia.ca/Mattituck-Hotels-Renovated-2-Bedroom-Guest-Cottage-Minutes-To-Beach-And-All-North-Fork-Activities.h92173172.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/56d08917.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/950f9d1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/1f68f090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, video library, offices](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/32e541f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage on Beach front Estate with Dockage .Walk to Village [](https://www.expedia.ca/Greenport-Hotels-Cottage-On-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34381035.Hotel-Information) Pipes Cove 10/10 Exceptional (74 reviews) "Wonderful stay at such a special spot. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Meg B. [](https://www.expedia.ca/Greenport-Hotels-Cottage-On-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34381035.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/83000000/82940000/82936400/82936348/w1500h997x0y2-eceb9339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/83000000/82940000/82936400/82936348/685e83e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82940000/82936400/82936348/1f52f3be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82940000/82936400/82936348/7b02cabc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Love Lane! Immaculately renovated private cottage. [](https://www.expedia.ca/Mattituck-Hotels-Immaculately-Renovated-Private-Cottage.h82936348.Hotel-Information) Mattituck 10/10 Exceptional (19 reviews) "The house is clean, comfortable, and has a lot of entertainment options." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joe M. [](https://www.expedia.ca/Mattituck-Hotels-Immaculately-Renovated-Private-Cottage.h82936348.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/65eee158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/93dc69f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/9e4cf8a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/777d29d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town [](https://www.expedia.ca/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information) Greenport 10/10 Exceptional (1 review) "Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeannette M. CA $387 CA $819 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73220000/73219200/73219181/65eeafef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/74000000/73220000/73219200/73219181/4734adc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73220000/73219200/73219181/1257e5f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/74000000/73220000/73219200/73219181/35e0d09d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Breakwater Beach in Heart of Wine Country [](https://www.expedia.ca/Mattituck-Hotels-Walk-To-Breakwater-Beach-In-Heart-Of-Wine-Country.h73219181.Hotel-Information) Mattituck 9.8/10 Exceptional (14 reviews) "The house and property were beautiful, clean and comfortable. The rooms are bright and airy. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bruce R. [](https://www.expedia.ca/Mattituck-Hotels-Walk-To-Breakwater-Beach-In-Heart-Of-Wine-Country.h73219181.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953500/94953488/cbf2bd2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953500/94953488/e5734c81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953500/94953488/d04ddc34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953500/94953488/6f683dbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mattituck Home w/ Fireplaces - Near Wineries [](https://www.expedia.ca/Mattituck-Hotels-Mattituck-Home-W-Fireplaces-Near-Wineries.h94953488.Hotel-Information) Mattituck [](https://www.expedia.ca/Mattituck-Hotels-Mattituck-Home-W-Fireplaces-Near-Wineries.h94953488.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/113000000/112270000/112269800/112269784/365a98f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112270000/112269800/112269784/fe9e4a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach towels](https://images.trvl-media.com/lodging/113000000/112270000/112269800/112269784/d340e1da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, DVD player](https://images.trvl-media.com/lodging/113000000/112270000/112269800/112269784/3c9cf28d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom cottage in fabulous Greenport [](https://www.expedia.ca/Greenport-Hotels-Charming-3-Bedroom-Cottage-In-Fabulous-Greenport.h112269784.Hotel-Information) Greenport 10/10 Exceptional (1 review) [](https://www.expedia.ca/Greenport-Hotels-Charming-3-Bedroom-Cottage-In-Fabulous-Greenport.h112269784.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76950000/76940600/76940515/324e7511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms](https://images.trvl-media.com/lodging/77000000/76950000/76940600/76940515/a0e0db70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76950000/76940600/76940515/f2fe1805.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/77000000/76950000/76940600/76940515/2836ef75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Picture Perfect Greenport Cottage [](https://www.expedia.ca/Greenport-Hotels-Picture-Perfect-Greenport-Cottage.h76940515.Hotel-Information) Greenport [](https://www.expedia.ca/Greenport-Hotels-Picture-Perfect-Greenport-Cottage.h76940515.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34340000/34335400/34335316/fda78027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/35000000/34340000/34335400/34335316/b6bf55f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34340000/34335400/34335316/306e7661.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach towels](https://images.trvl-media.com/lodging/35000000/34340000/34335400/34335316/a1338813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Cottage with New Heated Pool [](https://www.expedia.ca/Mattituck-Hotels-Modern-Cottage-With-New-Heated-Pool.h34335316.Hotel-Information) Mattituck 10/10 Exceptional (22 reviews) "Lovely property. Just perfect for a getaway. Convenient to Mattituck dining and shopping as well as to other towns on North Fork. Property owners were very helpful with any questions. Would love to stay and again and highly recommend it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan S. [](https://www.expedia.ca/Mattituck-Hotels-Modern-Cottage-With-New-Heated-Pool.h34335316.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83400000/83393400/83393376/8464c787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/84000000/83400000/83393400/83393376/270fa8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83400000/83393400/83393376/b0d65b87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83400000/83393400/83393376/9d89c09f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Craftsman Cottage in Greenport Village [](https://www.expedia.ca/Greenport-Hotels-Vintage-Cottage-In-Greenport-Village.h83393376.Hotel-Information) Greenport 10/10 Exceptional (1 review) "Me, my brother and sister in law, their son and his 1 year old daughter. The house suited us well. The house was well appointed and clean. Old craftsman house with nice modern kitchen and bathrooms. Bedrooms were a little tight with Queen beds but not a big deal. NIce big dining table for meals. Private back yard with picnic table. Quiet neighborhood with short walk to downtown." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George M. [](https://www.expedia.ca/Greenport-Hotels-Vintage-Cottage-In-Greenport-Village.h83393376.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38450000/38442600/38442552/4c3b0661.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/39000000/38450000/38442600/38442552/w1536h1149x0y3-55ba0c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38450000/38442600/38442552/e3a31bd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/39000000/38450000/38442600/38442552/e7345a70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Lakefront Cottage Near Town Beaches and North Fork Wineries [](https://www.expedia.ca/Southold-Hotels-Secluded-Lakefront-Cottage-Near-Town-Beaches-And-North-Fork-Wineries.h38442552.Hotel-Information) Southold 7.0/10 Good (9 reviews) "My husband and I rented this cottage for most of the summer and couldn't be happier with it. We lovingly refer to this place as The Pond Shack. The house is small and rustic so if you want a luxurious rental, this isn't for you. But if you want a low key retreat at an unbeatable price in an absolutely gorgeous location with beautiful views of the Great Pond (it's really more of a lake) and a 5 minute walk to the beach, then look no further. This place is perfect for 2 couples or a couple... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna B. [](https://www.expedia.ca/Southold-Hotels-Secluded-Lakefront-Cottage-Near-Town-Beaches-And-North-Fork-Wineries.h38442552.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/95000000/94510000/94504500/94504487/20d49013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94510000/94504500/94504487/49d8abed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94510000/94504500/94504487/c765f0e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94510000/94504500/94504487/ef236f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Near Wineries: Historic North Fork Farmhouse! [](https://www.expedia.ca/Cutchogue-Hotels-Historic-North-Fork-Farmhouse-Near-Wineries.h94504487.Hotel-Information) Cutchogue [](https://www.expedia.ca/Cutchogue-Hotels-Historic-North-Fork-Farmhouse-Near-Wineries.h94504487.Hotel-Information) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98556300/98556232/83245fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98556300/98556232/1ebc3dd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98556300/98556232/ea8c5d0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98556300/98556232/1e3c1b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southold Cottage w/ Patio & Grill - Walk to Beach! [](https://www.expedia.ca/Southold-Hotels-Southold-Cottage-W-Patio-Grill-Walk-To-Beach.h98556232.Hotel-Information) Southold [](https://www.expedia.ca/Southold-Hotels-Southold-Cottage-W-Patio-Grill-Walk-To-Beach.h98556232.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/38000000/37280000/37272600/37272527/c5e80976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/38000000/37280000/37272600/37272527/270-2280218d_edited_655c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms](https://images.trvl-media.com/lodging/38000000/37280000/37272600/37272527/1a01c4bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/38000000/37280000/37272600/37272527/b8810cab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute and simple summer cottage [](https://www.expedia.ca/Peconic-Hotels-Sweet-Simple-Summer-Cottage.h37272527.Hotel-Information) Peconic [](https://www.expedia.ca/Peconic-Hotels-Sweet-Simple-Summer-Cottage.h37272527.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=2026-02-04&endDate=2026-02-05®ionId=553248635976002319&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&lodging=CONDO) 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&lodging=COTTAGE) 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&lodging=VILLA) 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&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-Cottages.d553248635976002319-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Southold-Town-Cottages.d553248635976002319-aaCottages.Travel-Guide-Accommodation) ## Top Town of Southold Town Hotel Reviews ![Vine & Sand](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/a9ca389a_y.jpg) ### Vine & Sand 10/10 Excellent "Wonderful stay" [](https://expedia.ca/Southold-Hotels-Vine-Sand.h96718085.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 "The staff was wonderful and the room and views fantastic." [](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 "Friendly staff, area was cleaned " [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698399/w906h683x59y0-97f670df_y.jpg) ### Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office 10/10 Excellent "This hosts properties are so thoughtfully stocked, ,i felt home only nicer! Cabana is a real treat. Beautiful, new, clean, beautifully done. Every need of staying away in a home is thought of. Great area in walking distance to town as well. Host is always available for quick communications.well. " [](https://expedia.ca/Greenport-Hotels-Blue-Bay-Dream.h89698399.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) ![Zey Hotel](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg) ### Zey Hotel 10/10 Excellent "Quiet yet situated right in the heart of Greenport." [](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ![The SandPiper ](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/9eada5e0_y.jpg) ### The SandPiper 10/10 Excellent "Terrific service, clean, excellent location. " [](https://expedia.ca/Greenport-Hotels-The-SandPiper.h89698318.Hotel-Information) ![Greenporter Hotel](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg) ### Greenporter Hotel 10/10 Excellent "Staff looked tired," [](https://expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ## Find out more about Town of Southold Town ## Town of Southold Town Cottages information | Number of reviews | 438 | | ----------------- | ----------- | | Accommodation | 24 Cottages | | Lowest Price | CA $819 | | Highest Price | CA $819 | ## 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) - 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