Title: Town of Southold Town Cottages from CA $830 | 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) # Search Town of Southold Town Cottage Rentals from CA $830 ## 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=COTTAGE&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=COTTAGE&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=COTTAGE&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=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Featured Cottages in Town of Southold Town ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33504800/33504750/49305000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33510000/33504800/33504750/w799h599x1y1-106435ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33510000/33504800/33504750/10ac0400.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) ### Fabulous Waterfront Property in the Heart of Wine Country Peconic 10/10 Exceptional (182) "Beautiful view, clean house, great location " [](https://www.expedia.ca/Peconic-Hotels-Fabulous-Waterfront-Property-In-The-Heart-Of-Wine-Country.h33504750.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) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/077d4275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/7757c331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/dfbac7ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 'The Gate House'on Beach front Estate with Dockage. Walk to Village . Pipes Cove 9.8/10 Exceptional (99) "My husband and I brought our puppy. He had a great time running around the yard and beach. We enjoyed our stay and hope to return. The property is beautiful and we were very happy to find a pet friendly place on the water and close to town." [](https://www.expedia.ca/Greenport-Hotels-The-Gate-Houseon-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34201329.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) ![Exterior](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/172bc518.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) ![On the beach](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/08437262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage on Beach front Estate with Dockage .Walk to Village Pipes Cove 10/10 Exceptional (71) "Myself my BF and my dog had a wonderful time." [](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/33000000/32630000/32625000/32624902/a772a5a6.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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32630000/32625000/32624902/c671a85c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely Cottage in the Heart of Long Island Wine country Southold 9.8/10 Exceptional (29) "Our family stayed at this quaint cottage in the North Fork. The cottage has a nice kitchen, gas fireplace, and well appointed bedrooms. I would love to visit in summer, it must be wonderful!" [](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/93000000/92180000/92173200/92173172/4e7d9b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92180000/92173200/92173172/38688a26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92180000/92173200/92173172/d34c7fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92180000/92173200/92173172/317d49b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations! Mattituck 10/10 Exceptional (13) "What a great little get away weekend in a beautiful cottage in the middle of wine country. Great host a lovely accommodations" [](https://www.expedia.ca/Mattituck-Hotels-Renovated-2-Bedroom-Guest-Cottage-Minutes-To-Beach-And-All-North-Fork-Activities.h92173172.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) ![Interior](https://images.trvl-media.com/lodging/84000000/83420000/83412200/83412176/bb3bf8f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83420000/83412200/83412176/474b9031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83420000/83412200/83412176/2747ccc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Totally Renovated Cottage on the North Fork 7 min. walk to the Beach Cutchogue 10/10 Exceptional (27) "The property was clean, exactly as advertised and extremely cozy and convenient. The host was super helpful and quick to respond!" [](https://www.expedia.ca/Cutchogue-Hotels-Totally-Renovated-Cottage-On-The-North-Fork-7-Min-Walk-To-The-Beach.h83412176.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34880000/34879200/34879174/w1439h959x1y1-d17b928a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34880000/34879200/34879174/w1439h959x1y1-965e6dbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/35000000/34880000/34879200/34879174/w1439h959x1y1-deea6073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34880000/34879200/34879174/w1439h959x1y1-542c2ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely North Fork Beach Cottage (2 BR/2 bath)! Laurel 10/10 Exceptional (120) "Lovely cottage on the Peconic Bay. We enjoyed our stay; found more than everything we needed. " [](https://www.expedia.ca/Laurel-Hotels-Lovely-North-Fork-Beach-Cottage.h34879174.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33910000/33907500/33907423/975c5279.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33910000/33907500/33907423/0b5b7028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33910000/33907500/33907423/8d07ccc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33910000/33907500/33907423/5abf910c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Orient Village — Historic Bayfront Cottage — 2025 Season Orient 10/10 Exceptional (23) "Beautiful place with great views and a private beach! Great food and nature nearby, and very accommodating host!" [](https://www.expedia.ca/Orient-Hotels-Orient-Village-Historic-Bayfront-Cottage-2025-Season.h33907423.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94345100/94345066/2334e630.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) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94345100/94345066/e31d4df4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94345100/94345066/4d5e96b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Beach: Long Island Wine Country Home! Cutchogue [](https://www.expedia.ca/Cutchogue-Hotels-Home-In-Long-Island-Wine-Country-Walk-To-Beach.h94345066.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953500/94953488/06340227.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/f08caf8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953500/94953488/3f5c4f00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953500/94953488/3a0f65df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mattituck Home w/ Fireplaces - Near Wineries Mattituck [](https://www.expedia.ca/Mattituck-Hotels-Mattituck-Home-W-Fireplaces-Near-Wineries.h94953488.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) ![Smart TV, books](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/a165f45a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/c937e03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/1eb9ef8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town Greenport 10/10 Exceptional (1) "Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!" CA $391 CA $830 total includes taxes & fees Nov 3 - Nov 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) ![Interior](https://images.trvl-media.com/lodging/74000000/73220000/73219200/73219181/709627a0.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) ![Smart TV](https://images.trvl-media.com/lodging/74000000/73220000/73219200/73219181/4734adc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Breakwater Beach in Heart of Wine Country Mattituck 9.8/10 Exceptional (13) "Light filled, beautifully appointed home that was more than we expected. Gorgeous multiple outdoor areas. Seamless entry and exit. Would happily visit again. " [](https://www.expedia.ca/Mattituck-Hotels-Walk-To-Breakwater-Beach-In-Heart-Of-Wine-Country.h73219181.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82940000/82936400/82936348/294c6530.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) ![Game room](https://images.trvl-media.com/lodging/83000000/82940000/82936400/82936348/045e05bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82940000/82936400/82936348/2a361e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Love Lane! Immaculately renovated private cottage. Mattituck 10/10 Exceptional (18) "My wife and I stayed for the weekend for our Anniversary and this was the perfect location. Quaint and quite hideout with tons to do nearby." [](https://www.expedia.ca/Mattituck-Hotels-Immaculately-Renovated-Private-Cottage.h82936348.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112270000/112269800/112269784/0cd77338.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) ![Dining](https://images.trvl-media.com/lodging/113000000/112270000/112269800/112269784/888157b5.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/c09c0a4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom cottage in fabulous Greenport Greenport 10/10 Exceptional (1) [](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) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76950000/76940600/76940515/22b35c37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms](https://images.trvl-media.com/lodging/77000000/76950000/76940600/76940515/dc58cc62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76950000/76940600/76940515/608d8a1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Picture Perfect Greenport Cottage Greenport [](https://www.expedia.ca/Greenport-Hotels-Picture-Perfect-Greenport-Cottage.h76940515.Hotel-Information) ![Beach towels](https://images.trvl-media.com/lodging/35000000/34340000/34335400/34335316/a1338813.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/a9250692.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, memory foam beds, travel crib, free WiFi](https://images.trvl-media.com/lodging/35000000/34340000/34335400/34335316/e6a5dc4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Modern Cottage with New Heated Pool Mattituck 10/10 Exceptional (22) "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!" [](https://www.expedia.ca/Mattituck-Hotels-Modern-Cottage-With-New-Heated-Pool.h34335316.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83400000/83393400/83393376/2782ac10.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) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83400000/83393400/83393376/e20aa2d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83400000/83393400/83393376/efd6e02c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Craftsman Cottage in Greenport Village Greenport 10/10 Exceptional (1) "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." [](https://www.expedia.ca/Greenport-Hotels-Vintage-Cottage-In-Greenport-Village.h83393376.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38450000/38442600/38442552/adad4ed8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38450000/38442600/38442552/cfa88174.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/w1534h1152x2y0-db7bcf68.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) ### Secluded Lakefront Cottage Near Town Beaches and North Fork Wineries Southold 7.0/10 Good (9) "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... [](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/95000000/94510000/94504500/94504487/006b8f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94510000/94504500/94504487/0ffc3d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94510000/94504500/94504487/786b65bc.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! 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/a9b33bcb.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/a69aa101.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/cb5be822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southold Cottage w/ Patio & Grill - Walk to Beach! Southold [](https://www.expedia.ca/Southold-Hotels-Southold-Cottage-W-Patio-Grill-Walk-To-Beach.h98556232.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=COTTAGE&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-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 ![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 Cottages information | Number of reviews | 541 | | --- | --- | | Accommodation | 24 Cottages | | Lowest Price | CA $830 | | Highest Price | CA $830 | ## 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) - [Dering Harbor Hotels](https://www.expedia.ca/Dering-Harbor-Hotels.d553248634998885605.Travel-Guide-Hotels) - [Residences in Dering Harbor](https://www.expedia.ca/Dering-Harbor-Residences.d553248634998885605-aaResidences.Travel-Guide-Accommodation) - [Farmstay in East Marion](https://www.expedia.ca/East-Marion-Agritourism.d6069914-aaAgritourism.Travel-Guide-Accommodation) - [Cabin Rentals in East Marion](https://www.expedia.ca/East-Marion-Cabins.d6069914-aaCabins.Travel-Guide-Accommodation) - [B&B in Fishers Island](https://www.expedia.ca/Fishers-Island-Bed-And-Breakfast.d1208-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Fishers Island](https://www.expedia.ca/Fishers-Island-Guest-Houses.d1208-aaGuestHouses.Travel-Guide-Accommodation) - [Inns in Fishers Island](https://www.expedia.ca/Fishers-Island-Inns.d1208-aaInns.Travel-Guide-Accommodation) - [B&B in Greenport](https://www.expedia.ca/Greenport-Bed-And-Breakfast.d110728-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Greenport](https://www.expedia.ca/Greenport-Cabins.d110728-aaCabins.Travel-Guide-Accommodation) - [Adults Only Resorts & in Greenport](https://www.expedia.ca/Greenport-Hotels-Adults-Only-Resorts.0-0-d110728-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Beach-Hotel.0-0-d110728-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Boutique-Hotel.0-0-d110728-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Cheap-Hotels.0-0-d110728-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Greenport](https://www.expedia.ca/Greenport-Hotels-Couples-Resorts-Hotels.0-0-d110728-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Lake Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Lake-Hotels.0-0-d110728-tLakeHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Luxury-Hotel.0-0-d110728-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Oceanfront-Hotels.0-0-d110728-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Shopping-Hotel.0-0-d110728-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Spa-Hotel.0-0-d110728-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Waterpark-Hotels.0-0-d110728-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Greenport Hotels](https://www.expedia.ca/Greenport-Hotels.d110728.Travel-Guide-Hotels) - [Motels in Greenport](https://www.expedia.ca/Greenport-Motels.d110728-aaMotels.Travel-Guide-Accommodation) - [Hotels near Greenport Station](https://www.expedia.ca/Greenport-Station-Hotels.d6186190.Travel-Guide-Hotels) - [Beach Hotel Hotels in Greenport West](https://www.expedia.ca/Greenport-West-Hotels-Beach-Hotel.0-0-d553248635975876381-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Greenport West](https://www.expedia.ca/Greenport-West-Hotels-Cheap-Hotels.0-0-d553248635975876381-tCheapHotels.Travel-Guide-Filter-Hotels) - [Greenport West Hotels](https://www.expedia.ca/Greenport-West-Hotels.d553248635975876381.Travel-Guide-Hotels) - [Apartments in Mattituck](https://www.expedia.ca/Mattituck-Apartments.d6223780-aaApartments.Travel-Guide-Accommodation) - [B&B in Mattituck](https://www.expedia.ca/Mattituck-Bed-And-Breakfast.d6223780-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Mattituck](https://www.expedia.ca/Mattituck-Motels.d6223780-aaMotels.Travel-Guide-Accommodation) - [Guest Houses in New Suffolk](https://www.expedia.ca/New-Suffolk-Guest-Houses.d3000449151-aaGuestHouses.Travel-Guide-Accommodation) - [Motels in New Suffolk](https://www.expedia.ca/New-Suffolk-Motels.d3000449151-aaMotels.Travel-Guide-Accommodation) - [Vacation Homes in New Suffolk](https://www.expedia.ca/New-Suffolk-Private-Vacation-Homes.d3000449151-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [New York Hotels](https://www.expedia.ca/New-York-Hotels.d178293.Travel-Guide-Hotels) - [Chalets in North Haven](https://www.expedia.ca/North-Haven-Chalets.d553248634998589872-aaChalets.Travel-Guide-Accommodation) - [Residences in North Haven](https://www.expedia.ca/North-Haven-Residences.d553248634998589872-aaResidences.Travel-Guide-Accommodation) - [B&B in Noyack](https://www.expedia.ca/Noyack-Bed-And-Breakfast.d6217344-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Noyack](https://www.expedia.ca/Noyack-Guest-Houses.d6217344-aaGuestHouses.Travel-Guide-Accommodation) - [B&B in Orient](https://www.expedia.ca/Orient-Bed-And-Breakfast.d6326191-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Inns in Orient](https://www.expedia.ca/Orient-Inns.d6326191-aaInns.Travel-Guide-Accommodation) - [Resorts in Orient](https://www.expedia.ca/Orient-Resort-Hotels.d6326191-aaResortHotels.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Peconic](https://www.expedia.ca/Peconic-Hotels-Beach-Hotel.0-0-d144477-tBeachHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Peconic](https://www.expedia.ca/Peconic-Hotels-Ski-Hotel.0-0-d144477-tSkiHotel.Travel-Guide-Filter-Hotels) - [Peconic Hotels](https://www.expedia.ca/Peconic-Hotels.d144477.Travel-Guide-Hotels) - [Motels in Peconic](https://www.expedia.ca/Peconic-Motels.d144477-aaMotels.Travel-Guide-Accommodation) - [Vacation Homes in Peconic](https://www.expedia.ca/Peconic-Private-Vacation-Homes.d144477-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Villas in Peconic](https://www.expedia.ca/Peconic-Villas.d144477-aaVillas.Travel-Guide-Accommodation) - [Hotels near Pindar Vineyards](https://www.expedia.ca/Pindar-Vineyards-Hotels.0-l6326965-0.Travel-Guide-Filter-Hotels) - [B&B in Shelter Island](https://www.expedia.ca/Shelter-Island-Bed-And-Breakfast.d157359-aaBedAndBreakfast.Travel-Guide-Accommodation) - [B&B in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Bed-And-Breakfast.d183716-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Beach-Hotel.0-0-d183716-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Boutique-Hotel.0-0-d183716-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Couples-Resorts-Hotels.0-0-d183716-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Pet-Friendly-Hotel.0-0-d183716-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Spa-Hotel.0-0-d183716-tSpaHotel.Travel-Guide-Filter-Hotels) - [Shelter Island Heights Hotels](https://www.expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels) - [Resorts in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Resort-Hotels.d183716-aaResortHotels.Travel-Guide-Accommodation) - [Adults Only Resorts & in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Adults-Only-Resorts.0-0-d157359-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Beach-Hotel.0-0-d157359-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Boutique-Hotel.0-0-d157359-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Cheap-Hotels.0-0-d157359-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Couples-Resorts-Hotels.0-0-d157359-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Family-Hotel.0-0-d157359-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Hotel-With-Pool.0-0-d157359-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Hotels-With-Free-Breakfast.0-0-d157359-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Luxury-Hotel.0-0-d157359-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Oceanfront-Hotels.0-0-d157359-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Shopping-Hotel.0-0-d157359-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Shelter Island Hotels](https://www.expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels) - [Houseboats in Shelter Island](https://www.expedia.ca/Shelter-Island-Houseboats.d157359-aaHouseboats.Travel-Guide-Accommodation) - [Resorts in Shelter Island](https://www.expedia.ca/Shelter-Island-Resort-Hotels.d157359-aaResortHotels.Travel-Guide-Accommodation) - [Adults Only Resorts & in Silver Beach](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels-Adults-Only-Resorts.0-n553248635976481903-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Silver Beach Hotels](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels.0-n553248635976481903-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Southold](https://www.expedia.ca/Southold-Hotels-Cheap-Hotels.0-0-d183719-tCheapHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Southold](https://www.expedia.ca/Southold-Hotels-Romantic-Hotel.0-0-d183719-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Southold Hotels](https://www.expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels) - [Motels in Southold](https://www.expedia.ca/Southold-Motels.d183719-aaMotels.Travel-Guide-Accommodation) - [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 Southold](https://www.expedia.ca/lp/flights/183719/flights-from-southold) - [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) - [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)