Title: Town of Southold Town Cheap Hotels from CA $239: Book the Right Cheap Hotels Room in Town of Southold Town, New York - Expedia.ca [Town of Southold Town Travel Guide](https://expedia.ca/Town-Of-Southold-Town.dx553248635976002319)[Town of Southold Town Hotels](https://expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Hotel-Destinations)[Vacation Rentals in Town of Southold Town](https://expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Vacation-Rental-Destinations)[Town of Southold Town Car Rentals](https://expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Car-Rental-Destinations)[Town of Southold Town Vacations](https://expedia.ca/Town-Of-Southold-Town.d553248635976002319.Destination-Travel-Guides) ![Lavender farm on Long Island ](https://images.trvl-media.com/place/6069914/ada6e93d-1aa6-4a8f-b17b-ce0cc0fcdf57.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by gavvykins ![](https://images.trvl-media.com/place/6069914/ada6e93d-1aa6-4a8f-b17b-ce0cc0fcdf57.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## 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-Cheap-Hotels.0-0-d110728-tCheapHotels.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/dff376d916af97d7b1d400e631f0d46e.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Cutchogue [](https://expedia.ca/Cutchogue-Hotels-Cheap-Hotels.0-0-d183659-tCheapHotels.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Southold [](https://expedia.ca/Southold-Hotels-Cheap-Hotels.0-0-d183719-tCheapHotels.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/b87fd2222bd9c0b45cd653e0605bfed5.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Mattituck [](https://expedia.ca/Mattituck-Hotels-Cheap-Hotels.0-0-d6223780-tCheapHotels.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/c1e146be96c448a68862ae5f1f0cc1a9.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Peconic [](https://expedia.ca/Peconic-Hotels-Cheap-Hotels.0-0-d144477-tCheapHotels.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/f4b661641af8aca31895c5baaae02023.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Laurel [](https://expedia.ca/Laurel-Hotels-Cheap-Hotels.0-0-d6131264-tCheapHotels.Travel-Guide-Filter-Hotels) ## Check availability on Town of Southold Town Cheap Hotels Tonight [Feb 20 - Feb 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-02-20&endDate=2026-02-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) Tomorrow [Feb 21 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-02-21&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) This weekend [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) Next weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) ## Our top choices for Town of Southold Town cheap hotels ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/2c9cc7e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/7ebc6d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/717b3774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### The Harbor Front Inn [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) Greenport 8.8/10 Excellent (567 reviews) "Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $175 CA $239 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c.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) ![Terrace King | Living area](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/582203a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/90ac61e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Shoals Suites and Slips [](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) Southold 9.4/10 Exceptional (242 reviews) "Great stay, will definitely go again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ANTONIO J CA $216 CA $247 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/dc6eb455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/3451f87b.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) ![Breakfast served](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/29d9fdab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Menhaden [](https://www.expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information) Greenport 9.6/10 Exceptional (176 reviews) "Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cory CA $331 CA $433 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/81e91eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/d9d8edde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/65a6ec82.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) ### American Beech Hotel [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information) Greenport 8.8/10 Excellent (196 reviews) "Very nice and very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $212 CA $297 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information) ![Resort view](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c.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) ![Exterior](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/8a4a605e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/ac1b5094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sound View Greenport [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) Greenport 8.4/10 Very good (614 reviews) "Nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mateusz CA $204 CA $272 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.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](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/1c4953c1.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/fe6e5945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/2d824970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Sands Motel & Beach Bungalows [](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information) Greenport 9.8/10 Exceptional (144 reviews) "Everything was excellent, best hotel on the north fork. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dan [](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943259/2e6970b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943259/3faee5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, internet](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943259/3402d29d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943259/5ca46def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech - Luxury 2 Bedroom Apartment 10 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Luxury-2-Bedroom-Apartment-10.h71943259.Hotel-Information) Greenport 10/10 Exceptional (2 reviews) "This is an amazing hotel with high end finishes and a staff to match. The staff are polite, attentive, helpful in all ways and thoughtful in all their communication. I highly recommend to anyone looking for a boutique experience!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randall CA $368 CA $541 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Luxury-2-Bedroom-Apartment-10.h71943259.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-06&endDate=2026-03-07®ionId=553248635976002319&adults=2&travelerType=budget_property&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_553248635976002319) ![](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-Cheap-Hotels.0-0-d553248635976002319-tCheapHotels.Hotel-Filter-Destinations)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Town-Of-Southold-Town-Cheap-Hotels.0-0-d553248635976002319-tCheapHotels.Hotel-Filter-Destinations) ## Top Town of Southold Town Hotel Reviews ![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg) ### The Shoals Suites and Slips 10/10 Excellent "Clean and spacious room" [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Zey Hotel](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg) ### Zey Hotel 10/10 Excellent "Other guests mentioned that it was noisy, we heard nothing. Rooms are small, but perfect for a get away. Staff was helpful, kind, and courteous. Had a really nice stay." [](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ![American Beech Hotel](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/0caf92d6_y.jpg) ### American Beech Hotel 10/10 Excellent "Very nice and very clean." [](https://expedia.ca/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information) ![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 10/10 Excellent "Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return! " [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![The SandPiper ](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/9eada5e0_y.jpg) ### The SandPiper 10/10 Excellent "The host was very understanding about some last minute events that affected our trip" [](https://expedia.ca/Greenport-Hotels-The-SandPiper.h89698318.Hotel-Information) ![Vine & Sand](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/a9ca389a_y.jpg) ### Vine & Sand 10/10 Excellent "Vine + Sand was wonderful. The hosts were so friendly and it was close to many wineries." [](https://expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information) ![Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698399/w906h683x59y0-97f670df_y.jpg) ### Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office 10/10 Excellent "This hosts properties are so thoughtfully stocked, ,i felt home only nicer! Cabana is a real treat. Beautiful, new, clean, beautifully done. Every need of staying away in a home is thought of. Great area in walking distance to town as well. Host is always available for quick communications.well. " [](https://expedia.ca/Greenport-Hotels-Blue-Bay-Dream.h89698399.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Amazing room and view from the room was perfect! " [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![The Menhaden](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf_y.jpg) ### The Menhaden 10/10 Excellent "Loved our stay at the Menhaden! Everything was great especially the staff who went beyond our expectations...from offering us champagne and my husband a great mocktail to cleaning the snow off our car! The place is so pretty and the bar has all fun games & all albums you can play. The king room was large, no bath though :( and it was a bit cold in there, they did try and fix it though. Breakfast and goodies available all day on our floor with sodas, water, coffee and cappuccinos :). " [](https://expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Beach Hotel Hotels in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Beach-Hotel.0-0-d177851-tBeachHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Business-Hotel.0-0-d177851-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Honeymoon-Hotels.0-0-d177851-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Hotels-With-Waterslides.0-0-d177851-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Ski Hotels in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Ski-Hotel.0-0-d177851-tSkiHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Waterpark-Hotels.0-0-d177851-tWaterparkHotels.Travel-Guide-Filter-Hotels) - 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