Title: Top Hotels in Town of Southold Town | Expedia.ca [Town of Southold Town Travel Guide](https://expedia.ca/Town-Of-Southold-Town.dx553248635976002319)[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 Hotels ![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 ## Go beyond your typical stay in Town of Southold Town Pet friendly [](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=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&amenities=PETS) Apart hotel [](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=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&lodging=APART_HOTEL) Spa [](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=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&amenities=SPA_ON_SITE) Family friendly [](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=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&travelerType=family_friendly) Pool [](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=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&amenities=POOL) Ocean view [](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=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&amenities=OCEAN_VIEW) Hot tub [](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=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&amenities=HOT_TUB) Cabin [](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=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&lodging=CABIN) Apart­ment [](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=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&lodging=APARTMENT) Cottage [](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=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&lodging=COTTAGE) Condo [](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=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&lodging=CONDO) Waterpark [](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=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&amenities=WATER_PARK) ## 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-Hotels.d110728.Travel-Guide-Hotels) ![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Southold [](https://expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels) ![](https://mediaim.expedia.com/destination/2/dff376d916af97d7b1d400e631f0d46e.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Cutchogue [](https://expedia.ca/Cutchogue-Hotels.d183659.Travel-Guide-Hotels) ![](https://mediaim.expedia.com/destination/2/b87fd2222bd9c0b45cd653e0605bfed5.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Mattituck [](https://expedia.ca/Mattituck-Hotels.d6223780.Travel-Guide-Hotels) ![](https://mediaim.expedia.com/destination/1/d3e06c642f947ddad6aebc58401dad70.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Orient [](https://expedia.ca/Orient-Hotels.d6326191.Travel-Guide-Hotels) ![](https://mediaim.expedia.com/destination/2/c1e146be96c448a68862ae5f1f0cc1a9.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Peconic [](https://expedia.ca/Peconic-Hotels.d144477.Travel-Guide-Hotels) ![](https://mediaim.expedia.com/destination/2/64a7a541b17dabdb743e9908dec5b467.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### East Marion [](https://expedia.ca/East-Marion-Hotels.d6069914.Travel-Guide-Hotels) ![](https://mediaim.expedia.com/destination/2/f4b661641af8aca31895c5baaae02023.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Laurel [](https://expedia.ca/Laurel-Hotels.d6131264.Travel-Guide-Hotels) ## Check prices for these dates Tonight [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Hotels in Town of Southold Town ![Property grounds](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c7d19019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c3d8e2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/e78d099b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greenporter Hotel Greenport 9.2/10 Wonderful (257) "Staff was amazing and this hotel is in the perfect location " CA $184 CA $211 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/f76cf168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/55b708b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/4c9856c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sound View Greenport Greenport 8.4/10 Very good (574) "Loved everything about my stay at the Sound view !! " CA $347 CA $464 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Harbor View Balcony Junior Suite | Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/e407cc6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/64ea9871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/a8d80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harbor Front Inn Greenport 8.8/10 Excellent (521) "Great location ,beautiful hotel,nice staff" CA $231 CA $332 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/bfb5cc4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/942c49f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/20957ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Zey Hotel Greenport 9.2/10 Wonderful (275) "Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay." CA $368 CA $420 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ![Garden Suite King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/81035eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boardwalk Suite | Private kitchen](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/1898cf3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/efe41897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Shoals Suites and Slips Southold 9.6/10 Exceptional (209) "Great quick stay" CA $311 CA $391 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Beach bar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/52eefc00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/c930d525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Beach Shack Studio | View from room](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/8f5285b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/65a8ebbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Sands Motel & Beach Bungalows Greenport 9.8/10 Exceptional (132) "Beautiful beach all was great, loved breakfast At on site diner Nookies!" CA $364 CA $416 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/1638a16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo | Living area](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/w1446h1293x1y0-077b519e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/fa408cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water Edge, First Floor, Corner | Living area](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/e745edd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cliffside Resort Condominiums Greenport 9.0/10 Wonderful (241) "Great view of the water and nice amenities with the beach and pool." CA $313 CA $418 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast served](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/5b2ed019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/dc6eb455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/f0f56ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Menhaden Greenport 9.6/10 Exceptional (165) "Loved the vineyards that a were a couple of miles away " CA $431 CA $549 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/0caf92d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/9091cefd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (#1)](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/339409ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/52855a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech Hotel Greenport 9.0/10 Wonderful (193) "The property was clean beautiful and pleasant. Loved the trendy decor." CA $350 CA $456 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/a9ca389a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/63390424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/dd468523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/f10888a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vine & Sand Southold 10/10 Exceptional (11) "We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. " [](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/92000000/91480000/91472700/91472602/48ec4beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/92000000/91480000/91472700/91472602/d6c9f61c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/92000000/91480000/91472700/91472602/d7d73805.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/92000000/91480000/91472700/91472602/9b54ddd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Moraine Greenport 9.8/10 Exceptional (22) "Our 3rd stay - we love the beauty of the property and the luxurious serenity of this boutique hotel. Great views of the water; fantastic large pool and lounging areas." [](https://www.expedia.ca/Greenport-Hotels-Hotel-Moraine.h91472602.Hotel-Information) ![Beach/ocean view](https://images.trvl-media.com/lodging/2000000/1780000/1771100/1771009/d501821c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1780000/1771100/1771009/0ec625aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1780000/1771100/1771009/9698f5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1780000/1771100/1771009/8d30d692.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stirling House Bed & Breakfast Greenport 9.8/10 Exceptional (24) "Our stay was only 2 nights but felt like 5. Well rested 3 days. Would return in a Heart Beat. Clay was awesome and the breakfasts were over the top !" [](https://www.expedia.ca/Greenport-Hotels-Stirling-House-Bed-Breakfast.h1771009.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/c201860e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/5cc87916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/c8cd3b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/204773b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Arbor View House B&B East Marion 9.2/10 Wonderful (15) "Two mid age couples just had a good and relaxing time with great hospitality. " [](https://www.expedia.ca/East-Marion-Hotels-Arbor-View-House-Bed-And-Breakfast.h10328173.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/d47a17b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/f4e83179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/a22fa403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/c17eac68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbor Knoll Bed & Breakfast Pipes Cove 9.2/10 Wonderful (11) "It was very pleasant. We would stay again someday. Very convenient to restaurants in town and ferry. " [](https://www.expedia.ca/Greenport-Hotels-Harbor-Knoll-Bed-Breakfast.h22804880.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0195b6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/e69dbcaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/18f698b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/e500d985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - Petite King Room 7 Greenport 9.0/10 Wonderful (4) "Great job " CA $278 CA $428 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/91dd1778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/dd4148b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/35ce389c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/6f8236be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aqua Vista Pipes Cove 10/10 Exceptional (20) "Apartment was great for 2 couples and a baby. The location was amazing, 5 min walk to everything! Beds were super comfy!" [](https://www.expedia.ca/Greenport-Hotels-Aqua-Vista.h89698360.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/b0e39c6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/w2160h1436x0y5-12097315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/c1cf6b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/w2160h1432x0y4-657cfcb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbor Heights Pipes Cove 9.8/10 Exceptional (10) "This was a perfect location and such a cute place! The apartment was spotless and well appointed. " [](https://www.expedia.ca/Greenport-Hotels-Harbor-Heights.h102716809.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36200000/36197500/36197422/7895e25e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36200000/36197500/36197422/24a5012e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/37000000/36200000/36197500/36197422/e31e9dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36200000/36197500/36197422/9f3c6fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### White Blossom House Inn Southold 10/10 Exceptional (6) "Mark and Mona were great hosts. The house and grounds were beautiful. Southold is a great town to explore and the house is close to the beach and the town. We loved the use of the bicycles which made our trip much more fun. We could ride to the beach, the town, and the wineries. Mona even pumped my bike tires before we went to explore. Thanks for a great time and we hope to be back again next year !" [](https://www.expedia.ca/Southold-Hotels-White-Blossom-House-Inn.h36197422.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/10ef3e76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, printers](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/30fcbecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/a12114d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/52e5aba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautifully farmhouse Southold 10/10 Exceptional (3) "good experience" CA $836 CA $1,637 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Southold-Hotels-Magic-Place.h113098265.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/2db832c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/fdf24660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/123bbe23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/bc04c799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day Peconic 9.6/10 Exceptional (138) "We had a wonderful stay at Andrew's house! The pool, hot tub, yard, and poolhouse are meticulously maintained. My 2 children (ages 2 and 4) loved their time in the pool, playing on the large lawn, and using the hammock. The house itself has a full kitchen and laundry with a large dining table great for a family. The location was beautiful--very close to wineries and lots of farmstands. We drove about 12 minutes to Greenport for an excellent dinner. Andrew was very friendly and helpful. ... [](https://www.expedia.ca/Peconic-Hotels-NORTHFORK-COTTAGE-With-POOL-HOTTUB.h35037604.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&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%2FDestinations-In-Town-Of-Southold-Town.d553248635976002319.Hotel-Destinations)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Town-Of-Southold-Town.d553248635976002319.Hotel-Destinations) ## 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!" 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