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 ![](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 ## Go beyond your typical stay in Town of Southold Town 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=2025-11-08&d1=2025-11-08&endDate=2025-11-10&d2=2025-11-10&travelerType=family_friendly) 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=2025-11-08&d1=2025-11-08&endDate=2025-11-10&d2=2025-11-10&amenities=SPA_ON_SITE) 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=2025-11-08&d1=2025-11-08&endDate=2025-11-10&d2=2025-11-10&amenities=POOL) 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=2025-11-08&d1=2025-11-08&endDate=2025-11-10&d2=2025-11-10&amenities=HOT_TUB) 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=2025-11-08&d1=2025-11-08&endDate=2025-11-10&d2=2025-11-10&amenities=PETS) 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=2025-11-08&d1=2025-11-08&endDate=2025-11-10&d2=2025-11-10&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=2025-11-08&d1=2025-11-08&endDate=2025-11-10&d2=2025-11-10&lodging=COTTAGE) 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=2025-11-08&d1=2025-11-08&endDate=2025-11-10&d2=2025-11-10&amenities=OCEAN_VIEW) 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=2025-11-08&d1=2025-11-08&endDate=2025-11-10&d2=2025-11-10&amenities=WATER_PARK) 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=2025-11-08&d1=2025-11-08&endDate=2025-11-10&d2=2025-11-10&lodging=APART_HOTEL) Farm [](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=2025-11-08&d1=2025-11-08&endDate=2025-11-10&d2=2025-11-10&lodging=AGRITOURISM) 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=2025-11-08&d1=2025-11-08&endDate=2025-11-10&d2=2025-11-10&lodging=CONDO) ## Check prices for these dates Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-10-26&endDate=2025-10-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Hotels in Town of Southold Town ![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) ![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) ![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) ![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 (582) "Loved everything about my stay at the Sound view !! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sabrina CA $282 CA $391 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/a7102e12.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) ![Lobby](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c3d8e2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greenporter Hotel Greenport 9.2/10 Wonderful (273) "Great location, great service, very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christian [](https://www.expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.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) ![Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/64ea9871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/4e8534b4.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 (525) "Great location ,beautiful hotel,nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ROBERT CA $237 CA $339 total includes taxes & fees Nov 24 - Nov 25 [](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) ![Lobby](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/dc9e5678.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 (280) "Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexandra CA $368 CA $421 total includes taxes & fees Oct 26 - Oct 27 [](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 (216) "Great quick stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jasmine T CA $305 CA $384 total includes taxes & fees Nov 23 - Nov 24 [](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) ![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) ![Exterior](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/780134b3.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 (136) "Great hotel and location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyn CA $405 CA $463 total includes taxes & fees Nov 23 - Nov 24 [](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) ![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) ![Condo](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/d9295239.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) ### Cliffside Resort Condominiums Greenport 9.0/10 Wonderful (244) "Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) dean CA $313 CA $419 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) ![Sundeck](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/dc6eb455.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) ![1 bedroom, premium bedding, down comforters, memory foam beds](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/20266156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Menhaden Greenport 9.6/10 Exceptional (167) "Loved the vineyards that a were a couple of miles away " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $432 CA $550 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) ![Deluxe Suite | Living area](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/767aee45.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 8.8/10 Excellent (194) "The property was clean beautiful and pleasant. Loved the trendy decor." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $351 CA $457 total includes taxes & fees Oct 27 - Oct 28 [](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) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/59bbc572.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) ![Interior detail](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/dd468523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vine & Sand Southold 10/10 Exceptional (12) "This B&B, and its hosts, were simply amazing. I cannot recommend this place enough." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra [](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.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) ![Property grounds](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/7beade88.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) ![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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michail [](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) ![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) ![Lighthouse](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/3ee87f3c.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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea [](https://www.expedia.ca/Greenport-Hotels-Harbor-Knoll-Bed-Breakfast.h22804880.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) ![Lobby lounge](https://images.trvl-media.com/lodging/92000000/91480000/91472700/91472602/e7ab535b.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) ![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) ### 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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy [](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/2000000/1780000/1771100/1771009/9698f5a7.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) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1780000/1771100/1771009/0ec625aa.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 !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adam [](https://www.expedia.ca/Greenport-Hotels-Stirling-House-Bed-Breakfast.h1771009.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) ![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) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/9e0f05a8.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) ### American Beech in Greenport - Petite King Room 7 Greenport 9.0/10 Wonderful (4) "Great job " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) emilio CA $278 CA $414 total includes taxes & fees Oct 26 - Oct 27 [](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) ![Exterior detail](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/6f8236be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/35ce389c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aqua Vista Pipes Cove 10/10 Exceptional (22) "Great location and very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dwight R. [](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) ![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) ![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) ### 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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela [](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) ![Basic Apartment, Multiple Beds, Garden View | Living area](https://images.trvl-media.com/lodging/37000000/36200000/36197500/36197422/18b0f1c5.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) ![Exterior](https://images.trvl-media.com/lodging/37000000/36200000/36197500/36197422/24a5012e.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 !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) shannon [](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) ![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) ![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/5f36ce70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautifully farmhouse Southold 10/10 Exceptional (3) "good experience" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $839 CA $1,643 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Southold-Hotels-Magic-Place.h113098265.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943229/78e2058f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943229/e21d51ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943229/9a85fd03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943229/6f63cb0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech - King Suite 2 Greenport 10/10 Exceptional (2) "Excellent one night stay." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Patrick M. CA $293 CA $438 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-King-Suite.h71943229.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=2025-11-08&endDate=2025-11-09®ionId=553248635976002319&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Great weekend hotel deals in Town of Southold Town, NY Showing deals for:**Nov 7 - Nov 9** ![Exterior](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/c201860e.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) ### Arbor View House B&B East Marion **9.2/10**Wonderful (15 reviews) 10% off CA $554 CA $1,306 total includes taxes & fees [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-09&selected=10328173&adults=2) ![Exterior](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) ### Zey Hotel Greenport **9.2/10**Wonderful (280 reviews) 10% off CA $679 CA $1,552 total includes taxes & fees [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-09&selected=15622089&adults=2) ![Beach bar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/52eefc00.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) ### Silver Sands Motel & Beach Bungalows Greenport **9.8/10**Exceptional (136 reviews) 10% off CA $693 CA $1,583 total includes taxes & fees [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-09&selected=91068954&adults=2) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) ### Sound View Greenport Greenport **8.4/10**Very good (582 reviews) 10% off CA $792 CA $1,947 total includes taxes & fees [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-09&selected=15273178&adults=2) ![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) ### The Harbor Front Inn Greenport **8.8/10**Excellent (525 reviews) 10% off CA $534 CA $1,357 total includes taxes & fees [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-09&selected=43532300&adults=2) ![Garden Suite King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) VIP Access ### The Shoals Suites and Slips Southold **9.6/10**Exceptional (216 reviews) 10% off CA $675 CA $1,611 total includes taxes & fees [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-09&selected=76716269&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/1638a16b.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) ### Cliffside Resort Condominiums Greenport **9.0/10**Wonderful (244 reviews) 10% off CA $471 CA $1,197 total includes taxes & fees [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-09&selected=10449005&adults=2) ![](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 ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Breakfast and the Halyard restaurant are top shelf. A few quirks with our room(s) - no cable service, a locked bathroom door that couldn’t be opened, and a dead bolt that didn’t work- but the staff were helpful and accommodating and did everything they could to make things right." [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Zey Hotel](//images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg) ### Zey Hotel 10/10 Excellent "Hotel is centrally located in town. Staff was welcoming and warm. Free parking being the building. Lots of places to relax. " [](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.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) ![Surrounded by nature, come stay in this 1 bedroom private, serene location](//images.trvl-media.com/lodging/121000000/120190000/120181100/120181056/1bf16838_y.jpg) ### Surrounded by nature, come stay in this 1 bedroom private, serene location 10/10 Excellent "This apartment is on the lower level of a house, and the house is 10-15 minutes from every place we wanted to be. The bathroom and kitchen are newly renovated, and the very spiffy toaster oven heated up pizza quickly. There is an induction cook top for the more adventurous. I slept very well, but you will contend with about 10 pillows before you can get into bed. (My husband is not a decorative pillow guy). No issues with plumbing, electricity, or heat. Because it was my birthday on Friday, and we were stuck in so much traffic that we had to cancel our dinner reservations, I was really touched to see two small happy birthday cupcakes waiting." [](https://expedia.ca/Southold-Hotels-Surrounded-By-Nature.h120181056.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 Menhaden](//images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf_y.jpg) ### The Menhaden 10/10 Excellent "From the friendly check in with Mario to the check out everything was top class .The private bar is a really special touch and Dan was a great bar tender. The roof top is very nice to relax on with a glass of wine and the fire pit lit. Rooms are comfortable and spotless. There is a galley on each floor where they have coffee water and soda free all day plus fresh croissants in the morning .Highly recommend this hotel " [](https://expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.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 property" [](https://expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.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 "This property was insanely clean and well kept. Location lovely and close to restaurants wineries and farms to visit. Scenery pretty . Wished they had one more fire pit! " [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Cliffside Resort Condominiums](//images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/1638a16b_y.jpg) ### Cliffside Resort Condominiums 10/10 Excellent "Our unit was clean and neat. Beds and pillows could be upgraded (they were very soft). " [](https://expedia.ca/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information) ## Explore a world of travel with Expedia - Explore a world of travel with Expedia ### Hotels near top beaches in Town of Southold Town - [Hotels close to 67 Steps Beach](https://expedia.ca/67-Steps-Beach-Hotels.0-l553248626388140598-0.Travel-Guide-Filter-Hotels) - [Hotels close to Truman's Beach](https://expedia.ca/Trumans-Beach-Hotels.0-l553248635941390090-0.Travel-Guide-Filter-Hotels) ### Top cities in Town of Southold Town - [Greenport Hotels](https://expedia.ca/Greenport-Hotels.d110728.Travel-Guide-Hotels) - [Southold Hotels](https://expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels) - [Mattituck Hotels](https://expedia.ca/Mattituck-Hotels.d6223780.Travel-Guide-Hotels) - [Cutchogue Hotels](https://expedia.ca/Cutchogue-Hotels.d183659.Travel-Guide-Hotels) - [Orient Point Hotels](https://expedia.ca/Orient-Point-Hotels.d553248635074738584.Travel-Guide-Hotels) - [Peconic Hotels](https://expedia.ca/Peconic-Hotels.d144477.Travel-Guide-Hotels) - 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