Title: Town of Southold Town Cottages from CA $778 | 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 $778 ## Compare and save - ![](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 Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Featured Cottages in Town of Southold Town ![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) ![Interior](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/dcee1147.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 (102) "This was my second stay at the Gatehouse. It was as good as the first time. I have already made reservations to stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](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/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) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92180000/92173200/92173172/59606321.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) "Everything was clean and tastefully decorated. Check in was easy, with the host even able to get us in a couple hours early, which was highly appreciated.Spacious and accommodating, we loved our time here and would happily stay again the next time we’re in Mattituck!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael P. [](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) ![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) ![Exterior](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/172bc518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/cbb7065e.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 (72) "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/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) ![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) ![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) ### Fabulous Waterfront Property in the Heart of Wine Country Peconic 10/10 Exceptional (184) "Beautiful and cozy lakeside retreat. Super serene and peaceful place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel [](https://www.expedia.ca/Peconic-Hotels-Fabulous-Waterfront-Property-In-The-Heart-Of-Wine-Country.h33504750.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) ![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) ![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 (30) "We booked this beautiful cottage last minute for a quick weekend getaway and it was everything we hoped it would be. Eileen was also a pleasure to work with!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris S. [](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/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) "Bill was so friendly and inviting. Photos are accurate. Location is so close to gorgeous causeway beach. Minutes from main road- convenient for market runs and restaurants. Can’t wait to go back w my kids and husband." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marianna D. [](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/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) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33910000/33907500/33907423/5abf910c.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) ### Orient Village — Historic Bayfront Cottage — 2025 Season Orient 10/10 Exceptional (23) "Step away from your busy schedule, step back in time, and step down to the beach. Bayside Cottage is an idyllic, charming, and rare place -- one increasingly harder to find as grandiose properties populate many parts of the Island. Thankfully the North Fork has retained much of its character since we began visiting some 20 years ago, and Orient is beautifully preserved with a lot of tender loving care, especially towards nature. It was turtle season in June! At Bayside, circa 1887, one doesn't... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer G. CA $420 CA $994 total includes taxes & fees Nov 30 - Dec 1 [](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/95000000/94350000/94345100/94345066/5cef20fa.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) ### 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) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/65eee158.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) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/51cab21c.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) ### 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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeannette M. CA $350 CA $778 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.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/95000000/94960000/94953500/94953488/3a0f65df.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/95000000/94960000/94953500/94953488/77dbb2dc.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) ![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 (14) "My family and I enjoyed our stay. Carl was quick to respond and friendly. The house was very clean and fresh feeling with a minimalist yet warm atmosphere. The neighborhood is very quiet and peaceful. I would rent it again but request a beach parking pass as the walk is a bit far for kids. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) abigail s. [](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) ![Dining](https://images.trvl-media.com/lodging/83000000/82940000/82936400/82936348/685e83e6.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) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82940000/82936400/82936348/1f52f3be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Love Lane! Immaculately renovated private cottage. Mattituck 10/10 Exceptional (18) "Perfect for couple seeking getaway in north fork" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick C. [](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) ![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) ![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) ![Beach towels](https://images.trvl-media.com/lodging/113000000/112270000/112269800/112269784/d340e1da.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) ![3 bedrooms](https://images.trvl-media.com/lodging/77000000/76950000/76940600/76940515/dc58cc62.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) ![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) ![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) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34340000/34335400/34335316/4821d8c7.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!" ![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/84000000/83400000/83393400/83393376/2782ac10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/84000000/83400000/83393400/83393376/5dc57931.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) ### 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." ![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) ![Exterior](https://images.trvl-media.com/lodging/39000000/38450000/38442600/38442552/adad4ed8.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) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38450000/38442600/38442552/a17cf4ff.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) ### 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... ![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/95000000/94510000/94504500/94504487/006b8f42.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/ef236f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94510000/94504500/94504487/f99acbdc.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/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/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/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) ![Exterior](https://images.trvl-media.com/lodging/38000000/37280000/37272600/37272527/c5e80976.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) ![3 bedrooms](https://images.trvl-media.com/lodging/38000000/37280000/37272600/37272527/1a01c4bf.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) ### Cute and simple summer cottage 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=2025-11-16&endDate=2025-11-17®ionId=553248635976002319&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%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 ![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 "Everything was Amazing! " [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.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 "amazing stay, very quaint and relaxing " [](https://expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Beautiful Long Island Sound and sunset views." [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.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 "Beautiful view and room. Staff friendly and accommodating. Excellent location. " [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Zey Hotel](//images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg) ### Zey Hotel 10/10 Excellent "Such a cute little hotel. Stayed one night bc we had a wedding in the area. Everything was great - the staff was exceptional." [](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ![The Menhaden](//images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf_y.jpg) ### The Menhaden 10/10 Excellent "Hotel manager was great! Loved the firepits outside " [](https://expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information) ![Greenporter Hotel](//images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg) ### Greenporter Hotel 10/10 Excellent "Great place. Would come again" [](https://expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ![Vine & Sand](//images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/a9ca389a_y.jpg) ### Vine & Sand 10/10 Excellent "This B&B, and its hosts, were simply amazing. I cannot recommend this place enough." [](https://expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information) !['The Gate House'on Beach front Estate with Dockage. Walk to Village .](//images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/077d4275_y.jpg) ### 'The Gate House'on Beach front Estate with Dockage. Walk to Village . 10/10 Excellent "Adorable cottage on the water. Spotless. Has everything you need for a simple vintage getaway!" [](https://expedia.ca/Greenport-Hotels-The-Gate-Houseon-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34201329.Hotel-Information) ## Find out more about Town of Southold Town ## Town of Southold Town Cottages information | Number of reviews | 442 | | --- | --- | | Accommodation | 24 Cottages | | Lowest Price | CA $778 | | Highest Price | CA $994 | ## 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) - 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