Title: Book The Best Hotels in Southold, NY for 2026 from CA $104 - Fully Refundable Options - Expedia.ca [Vacation Rentals in Southold](https://expedia.ca/Southold-Vacation-Rentals.d183719.Travel-Guide-VacationRentals)[Flights to Southold](https://expedia.ca/Cheap-Flights-To-Southold.d183719.Travel-Guide-Flights)[Southold Car Rentals](https://expedia.ca/Car-Rentals-In-Southold.d183719.Car-Rental-Guide)[Southold Vacation Packages](https://expedia.ca/Southold.d183719.Destination-Travel-Guides) ![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Benny Goh ![](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.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 ## Go beyond your typical stay in Southold Pool [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&amenities=POOL) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&amenities=PETS) Ocean view [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&amenities=OCEAN_VIEW) Spa [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&amenities=SPA_ON_SITE) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&amenities=HOT_TUB) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&travelerType=family_friendly) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&lodging=COTTAGE) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&lodging=APARTMENT) Waterpark [](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-15&d2=2026-02-15&amenities=WATER_PARK) ## Check prices for these dates Tonight [Jan 30 - Jan 31](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-30&endDate=2026-01-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 31 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-31&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Southold hotels ![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) ![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) ![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) ### The Shoals Suites and Slips [](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) Southold 9.4/10 Exceptional (238 reviews) "Great stay, will definitely go again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ANTONIO J CA $220 CA $252 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/242d28e0.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) ![Private beach nearby, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/e94ab56a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/70895a0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vine & Sand [](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information) Southold 9.6/10 Exceptional (15 reviews) "Wonderful stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judy [](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/dc9b088b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, hair dryer, towels, soap](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/afd83ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/735ceae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Guilford [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) Guilford 8.8/10 Excellent (88 reviews) "The front desk staff were excellent, clean and comfortable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JUstine CA $145 CA $167 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/147e40ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/cfee764e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/ee8b7737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/f90ba663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shorewood Inn [](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information) Riverhead 8.4/10 Very good (718 reviews) "ROOM WAS CLEAN, WARM, GOOD PARKING" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JOSEPH [](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/72f65e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a48f4b96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/31bd2f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pier Blue Inn Old Saybrook - Essex [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) Saybrook Manor 8.0/10 Very good (1,000 reviews) "A welcoming place with some nice touches." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/2d17124a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio, Private Bathroom (King Size Bed)](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/65285c66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/e3411bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, Private Bathroom | Private kitchen](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/733470c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Niantic Inn [](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information) Niantic 9.2/10 Wonderful (137 reviews) "Quiet and warm and clean. Nice touch from Housekeeping too! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $120 CA $138 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information) ![Indoor pool, open 9:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/0b15e4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/be26a516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/604acd23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Old Saybrook - Westbrook [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) Old Saybrook 7.8/10 Good (1,001 reviews) "Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $134 CA $154 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.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 (608 reviews) "Nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mateusz CA $164 CA $226 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/6b467104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/32676408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/0d39535c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/89db28cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Long Island-East End by IHG [](https://www.expedia.ca/Riverhead-Hotels-Holiday-Inn-Express-Hotel-Suites-Long-Island-East-End.h1376205.Hotel-Information) Riverhead 8.6/10 Excellent (1,003 reviews) "Quality hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $139 CA $159 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Riverhead-Hotels-Holiday-Inn-Express-Hotel-Suites-Long-Island-East-End.h1376205.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/9ab5b9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f2520f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free cribs/infant beds, rollaway beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/d1788901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7836a152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clinton Motel [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) Clinton 8.6/10 Excellent (301 reviews) "The room was comfortable and clean. A good value for the money." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $103 CA $118 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/85851742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach nearby, beach towels](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/8a104c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/d096a355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/8ac37006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hamlet Inn [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) Southampton 8.6/10 Excellent (448 reviews) "Room was in good condition however I found the shower to be extremely small despite having great water pressure and extremely nice temperature." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) gail CA $117 CA $151 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine, pool views ](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/a6b9753f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/75016698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/ecf5693f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/65c6d537.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Indigo Long Island - East End by IHG [](https://www.expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.Hotel-Information) Riverhead 8.8/10 Excellent (1,000 reviews) "The places lovely good restaurant. Nice dinner excellent complimentary breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caroline CA $142 CA $162 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/df127760.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9b1283d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/56b46a8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/003f8776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Long Island East End [](https://www.expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) Riverhead 9.2/10 Wonderful (1,001 reviews) "Tamara, who checked us in, made a great first impression. She was friendly, helpful, and very accommodating." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kameron CA $153 CA $175 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/cc53a2c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/b432d22f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/1bfd9996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/4bbf34cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bentley Hotel Southampton [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) Southampton 9.6/10 Exceptional (432 reviews) "Adorable room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martin CA $148 CA $171 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/b5361d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/2ffae8cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/ff7ccdb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/039bea88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott New York Long Island East End [](https://www.expedia.ca/Riverhead-Hotels-Residence-Inn-By-Marriott-New-York-Long-Island-East-End.h18516036.Hotel-Information) Riverhead 9.0/10 Wonderful (1,000 reviews) "great place,I loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan CA $148 CA $169 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Riverhead-Hotels-Residence-Inn-By-Marriott-New-York-Long-Island-East-End.h18516036.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/2c9cc7e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/1345db22.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) ![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 (563 reviews) "Everything was Great Immaculate hotel very good location sraff was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) latoya CA $176 CA $239 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/51be5ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/c4264a32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/77fe5437.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/07ec8098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House on Chase Creek [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information) The Heights 9.4/10 Exceptional (80 reviews) "Great stay. The host is amzing and very helpful. The house is peaceful and safe!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marshella CA $140 CA $161 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/849992dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/w3837h2557x3y3-b7e16408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/w3837h2557x3y3-55740709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/w3837h2557x3y3-564a2b5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Riverhead [](https://www.expedia.ca/Riverhead-Hotels-Hilton-Garden-Inn-Riverhead.h1962521.Hotel-Information) Riverhead 8.6/10 Excellent (1,000 reviews) "The amenities were great! Staff was amazing! Overall a great stay. Will be back soon!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Candace CA $149 CA $171 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Riverhead-Hotels-Hilton-Garden-Inn-Riverhead.h1962521.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) ![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) ![Reception](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/65a6ec82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/6603a689.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 (195 reviews) "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 $209 CA $293 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/0820f8f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/b026cb5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/a27d78bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/61b6e714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Inn & Suites Old Saybrook Westbrook [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) Old Saybrook 7.2/10 Good (466 reviews) "All good it met our expectations as a budget hotel. Large clean room bed was comfortable although the pillows were past it. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hilary CA $88 CA $102 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.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=2026-02-13&endDate=2026-02-14®ionId=183719&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%2FSouthold-Hotels.d183719.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Hotels.d183719.Travel-Guide-Hotels) ## Stay near popular Southold attractions ### Sparkling Pointe 4.5/5 (2 reviews) You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6327589) ### Horton Lane Beach 4.0/5 (1 review) Why not spend a lazy afternoon at Horton Lane Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248635983992604) ### Sannino's Bella Vita Vineyard You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6327435) ### Croteaux Vineyards You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6326852) ### The Old Field Vineyards 4.0/5 (1 review) You can enjoy a tasting or tour at The Old Field Vineyards during your travels to Southold. Stroll along the beaches or discover the sunsets in this family-friendly area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6327777) ### Osprey's Dominion You can enjoy a tasting or tour at Osprey's Dominion during your travels to Southold. Wander the beautiful beaches in this family-friendly area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6326243) ### Corey Creek Winery You can enjoy a tasting or tour at Corey Creek Winery during your travels to Southold. Wander the beautiful beaches in this family-friendly area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6326844) ### Horton Point Park Explore the great outdoors at Horton Point Park, a lovely green space in Southold. Wander the beaches or discover the sunsets in this family-friendly area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6064489) ## Learn more about Southold Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip. [See all hotels in Southold](https://www.expedia.ca/Hotel-Search?startDate=2026-02-13&endDate=2026-02-14&adults=2®ionId=183719) ![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=899&h=600&p=1&q=high) Photo by Benny Goh ## Top Southold Hotel Reviews ![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 10/10 Excellent "Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area. " [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Hyatt Place Long Island East End](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb_y.jpg) ### Hyatt Place Long Island East End 10/10 Excellent "Tamara, who checked us in, made a great first impression. She was friendly, helpful, and very accommodating." [](https://expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) ![Hotel Indigo East End by IHG](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/75016698_y.jpg) ### Hotel Indigo East End by IHG 10/10 Excellent "Staff was amazing especially with a major storm coming. Food was terrific as well." [](https://expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.Hotel-Information) ![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "All good. Peyton was very helpful, as well as all the other staff. Beautiful view - snowed in! Thanks. " [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Residence Inn by Marriott New York Long Island East End](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/b5361d70_y.jpg) ### Residence Inn by Marriott New York Long Island East End 10/10 Excellent "Absolutely and I'm finally happy and safe with my fiance and I. So thank you 😊 " [](https://expedia.ca/Riverhead-Hotels-Residence-Inn-By-Marriott-New-York-Long-Island-East-End.h18516036.Hotel-Information) ![Holiday Inn Express Hotel & Suites Long Island-East End by IHG](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/6b467104_y.jpg) ### Holiday Inn Express Hotel & Suites Long Island-East End by IHG 10/10 Excellent "Clean, helpful staff, comfy pillows and bed. Slept like a baby " [](https://expedia.ca/Riverhead-Hotels-Holiday-Inn-Express-Hotel-Suites-Long-Island-East-End.h1376205.Hotel-Information) ![The Preston House & Hotel](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/1f765cec_y.jpg) ### The Preston House & Hotel 10/10 Excellent "Everyone was very helpful and nice, the room was amazing. Super clean and modern. " [](https://expedia.ca/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information) ![Hilton Garden Inn Riverhead](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/82ff92d7_y.jpg) ### Hilton Garden Inn Riverhead 10/10 Excellent "The amenities were great! Staff was amazing! Overall a great stay. Will be back soon!" [](https://expedia.ca/Riverhead-Hotels-Hilton-Garden-Inn-Riverhead.h1962521.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "I have stayed here a number of times, and each time the room has been spotless and smells fresh. The staff is very friendly and always offers to help in some way, whether it's to get the snow off my car or provide bottled water. I will be staying here again!" [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ## More cheap stays in Southold ![Budget Host East End Hotel in Riverhead](https://images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/ad0c5cd3_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Budget Host East End Hotel in Riverhead 30 Lake Avenue Riverhead NY CA $126 CA $144 total Feb 1 - Feb 2 includes taxes & fees 6.6/10 (794 reviews) [](https://expedia.ca/Riverhead-Hotels-Budget-Host-East-End-Hotel-In-Riverhead.h1130479.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn Old Saybrook - Westbrook 100 Essex Rd Old Saybrook CT CA $136 CA $157 total Feb 5 - Feb 6 includes taxes & fees 7.6/10 Good! (1,000 reviews) [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Spark by Hilton Guilford](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Spark by Hilton Guilford 300 Boston Post Rd Guilford CT CA $145 CA $167 total Feb 17 - Feb 18 includes taxes & fees 8.8/10 Excellent! (85 reviews) [](https://expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Bentley Hotel Southampton 161 Hills Station Rd Southampton NY CA $148 CA $171 total Feb 9 - Feb 10 includes taxes & fees 9.4/10 Exceptional! (431 reviews) [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Pier Blue Inn Old Saybrook - Essex 1430 Boston Post Rd Old Saybrook CT [Get rates](https://expedia.ca/Hotel-Search?startDate=13%2F02%2F2026&endDate=14%2F02%2F2026&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true®ionId=183719) 7.8/10 Good! (1,002 reviews) [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Atlantic Hotel 1655 County Road 39 Southampton NY [Get rates](https://expedia.ca/Hotel-Search?startDate=13%2F02%2F2026&endDate=14%2F02%2F2026&selected=447803&PinnedHotelID=447803&HadPinnedHotel=true®ionId=183719) 7/10 Good! (978 reviews) [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ## Hotels in Southold with star rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg) 5 Star Hotels 2 properties [](https://expedia.ca/5Star-Southold-Hotels.s50-0-d183719.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 54 properties [](https://expedia.ca/4Star-Southold-Hotels.s40-0-d183719.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 239 properties [](https://expedia.ca/3Star-Southold-Hotels.s30-0-d183719.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 254 properties [](https://expedia.ca/2Star-Southold-Hotels.s20-0-d183719.Travel-Guide-Filter-Hotels) ## Find out more about Southold ### Top reasons to visit Southold - **Picturesque Beaches:** Southold features stunning sandy shores, perfect for relaxing or enjoying a family day by the water. - **Outdoor Adventures:** Engage in various activities like paddleboarding in the summer or skiing in the winter. - **Local Culture:** Explore charming spots like the Southold Fish Market for a taste of local flavours. - **Scenic Picnic Areas:** Enjoy beautiful picnic spots amidst Southold's natural beauty. - **Diverse Accommodations:** Choose from a range of lodging options, including family-friendly and pet-friendly stays. ### Find great hotels near Southold Southold, New York, offers a diverse array of accommodations to cater to every traveller's needs, from family-friendly stays to pet-friendly options. Notably, the Southold Beach Motel stands out for its charming atmosphere and proximity to the stunning shoreline. Whether you're seeking adventure or a relaxing getaway, you'll find the perfect lodging to enhance your experience in this picturesque coastal town. - **[Sound View Greenport: ](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)** Nestled along the picturesque shoreline, Sound View Greenport offers a delightful blend of beachside relaxation and family-friendly amenities. This 3.5-star hotel is perfect for those looking to unwind by the water while enjoying a range of activities suitable for all ages. With direct beach access, you can soak up the sun or partake in water sports. Business travellers will appreciate the well-equipped meeting rooms and conference space, while families can take advantage of amenities designed for children, including free cribs and window guards for added safety. - **[Sag Harbor Inn: ](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)** Located a short drive from Southold, Sag Harbor Inn is an excellent choice for business travellers seeking a tranquil environment. This 3.5-star hotel is designed with professionalism in mind, offering essential business amenities including a meeting room that caters to corporate needs. The hotel's serene surroundings provide a peaceful atmosphere, allowing you to focus on your work while enjoying the charm of Sag Harbor. Guests have noted the attentive service and comfortable accommodations that make this inn a reliable option for business trips. - **[The Harbor Front Inn: ](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)** The Harbor Front Inn stands out as a pet-friendly haven for travellers wanting to bring their furry companions along. This 3.5-star hotel, conveniently located near Southold, combines business amenities with a welcoming atmosphere for pets. With policies that allow dogs and service animals, you won't have to leave your pet behind. Business travellers can benefit from a range of facilities designed to cater to their needs, while enjoying the unique experience of a waterfront stay. Guests have praised the incredible location and accommodating staff, ensuring a comfortable visit for both you and your pet. ### Where to stay near Southold Southold, New York, offers an idyllic vacation experience perfect for outdoor enthusiasts and couples alike. With its stunning beaches and beachfront locations, it's an ideal beach getaway for families and those seeking relaxation. Nearby attractions provide a blend of scenic beauty, historical charm, and luxury excursions. Whether you're enjoying sunny weather or planning a weekend escape, Southold promises a delightful atmosphere for every traveller. - **[Hamptons: ](https://www.expedia.ca/Hamptons-Hotels.d6056452.Travel-Guide-Hotels)** Located a mere 16.1km from Southold, the Hamptons are a quintessential summer destination known for their beautiful beaches and upscale charm. This area sees a peak in visitors from June to August, attracting those seeking a beach , outdoor , and romantic experience. With golf courses, music concerts, and luxurious resorts, there’s no shortage of activities to indulge in. Additionally, the picturesque local landmarks, including family-friendly beaches and serene lakes, make the Hamptons a perfect getaway for relaxation and recreation. - **[Greenport: ](https://www.expedia.ca/Greenport-Hotels.d110728.Travel-Guide-Hotels)** Just 6.4km away from Southold, Greenport is a charming city that offers a delightful mix of outdoor activities and romantic vibes. Like the Hamptons, Greenport experiences peak travel from June to August, drawing visitors who enjoy beaches and local events. Golf courses and music concerts abound, providing ample entertainment options. The proximity to beautiful beaches and event conference venues adds to Greenport’s appeal, making it a must-visit for those looking to experience the coastal lifestyle. - **[Sag Harbor: ](https://www.expedia.ca/Sag-Harbor-Hotels.d154327.Travel-Guide-Hotels)** Located 12.9km from Southold, Sag Harbor is a picturesque city that perfectly encapsulates a coastal retreat. The area enjoys a moderate influx of visitors, especially from June to August, who come for its outdoor , beach , and romantic experiences. From golf courses to ski fields, the range of activities is impressive. Sag Harbor is also home to beautiful beaches, family parks, and scenic spots, making it an ideal location for both adventure and relaxation. ### Things to do near Southold Southold, New York, is perfect for a romantic and outdoor getaway, offering a variety of activities. Enjoy relaxing beach days on the sandy shores, have a picnic in scenic areas, or soak up the sun on the terrace. For the adventurous, paddleboard rentals are available, and there are opportunities for winter sports like skiing. Additionally, music concerts provide entertainment options, making Southold an ideal vacation destination. **Shopping** In Southold, visit the [Greenport Farmers' Market](https://www.expedia.ca/Greenport-Farmers-Market-Hotels.0-l553248621532665744-0.Travel-Guide-Filter-Hotels), only 6.4km away, for fresh produce and local crafts. [The Style Bar](https://www.expedia.ca/The-Style-Bar-Hotels.0-l553248621532665737-0.Travel-Guide-Filter-Hotels) and [BookHampton](https://www.expedia.ca/BookHampton-Hotels.0-l553248621532665731-0.Travel-Guide-Filter-Hotels), both 12.9km away, offer unique fashion and books. If you're up for a drive, check out larger malls in nearby towns for more extensive shopping options. **Recreation** [Goldsmith's Inlet Park](https://www.expedia.ca/Goldsmiths-Inlet-Park-Hotels.0-l6326890-0.Travel-Guide-Filter-Hotels) offers a tranquil escape with its calming natural surroundings, perfect for relaxation and rejuvenation. For those seeking sport and outdoor fun, [Noyac Golf Club](https://www.expedia.ca/Noyac-Golf-Club-Hotels.0-l6064499-0.Travel-Guide-Filter-Hotels) provides a beautiful golf experience, while [Shelter Island Whale's Tail](https://www.expedia.ca/Shelter-Island-Whales-Tail-Hotels.0-l553248621554204762-0.Travel-Guide-Filter-Hotels) mini-golf promises family-friendly adventure in a delightful setting. **Adventure** Experience thrilling water rides at [Splish Splash Water Park](https://www.expedia.ca/Splish-Splash-Water-Park-Hotels.0-l6173416-0.Travel-Guide-Filter-Hotels), located 30.6km from Southold, perfect for family fun. For adrenaline junkies, [Riverhead Raceway](https://www.expedia.ca/Riverhead-Raceway-Hotels.0-l6173429-0.Travel-Guide-Filter-Hotels) offers exciting motor racing action, situated 29.0km away. Don't miss the scenic [Walking Dunes Trailhead](https://www.expedia.ca/Walking-Dunes-Trailhead-Hotels.0-l553248633992587102-0.Travel-Guide-Filter-Hotels), 33.8km from Southold, for a picturesque hiking adventure. **Nightlife** Experience the charm of the [Greenport Carousel](https://www.expedia.ca/Greenport-Carousel-Hotels.0-l553248635961252285-0.Travel-Guide-Filter-Hotels), just 6.4km away, offering a whimsical outdoor vibe. For a touch of culture and romance, head to [Bay Street Theatre](https://www.expedia.ca/Bay-Street-Theatre-Hotels.0-l6326787-0.Travel-Guide-Filter-Hotels), 12.9km from Southold, or [Guild Hall](https://www.expedia.ca/Guild-Hall-Hotels.0-l6323757-0.Travel-Guide-Filter-Hotels), 16.4km away, both perfect for family entertainment. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Southold To save money on your trip to Southold, consider visiting between January and March when accommodation prices drop. Tuesdays tend to be the least expensive days to stay, while Saturdays are pricier. Use Expedia's search tool to find budget-friendly hotels by sorting prices from lowest to highest and filtering for eco-friendly options. Additionally, you can save by booking a package that combines your hotel, flights, and activities. Exploring the area on foot is a great way to enjoy free activities while keeping transport costs down. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Southold are January to March, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Southold is Tuesday. The most expensive day to stay in Southold is Saturday. - **Find cheap hotels on Expedia:** Expedia’s search tool enables you to specify your budget, preferred destination, and additional criteria. You can arrange your search results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Furthermore, you have the option to narrow down your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly accommodations that you can book. - **Consider bundling your trip:** You can potentially save some money by combining your Southold hotel reservation with your flights and activities through an Expedia package. ### Find the best attractions near Southold Southold, New York, is perfect for outdoor enthusiasts and romantic getaways, offering a blend of beach experiences, cultural attractions, and history. Visitors can enjoy the scenic Southold Town Beach and explore local gems like the Southold Fish Market. The area caters to those seeking relaxation by the shore, engaging outdoor activities, and a taste of local culture, making it an ideal destination for a memorable vacation. - **[67 Steps Beach: ](https://www.expedia.ca/67-Steps-Beach-Hotels.0-l553248626388140598-0.Travel-Guide-Filter-Hotels)** Located 8.0km from Southold, 67 Steps Beach offers a delightful seaside experience with its picturesque views and relaxing beach vibes. It's perfect for sunbathing, swimming, and enjoying the tranquil sounds of the waves. - **[Railroad Museum of Long Island: ](https://www.expedia.ca/Railroad-Museum-Of-Long-Island-Hotels.0-l6327144-0.Travel-Guide-Filter-Hotels)** Just 6.4km away, this cultural gem showcases the rich history of Long Island's railroads. Explore fascinating exhibits and learn about the region's transportation heritage in a family-friendly environment. - **[Sag Harbor Marine Park: ](https://www.expedia.ca/Sag-Harbor-Marine-Park-Hotels.0-l6327316-0.Travel-Guide-Filter-Hotels)** Situated 12.9km from Southold, this marina is ideal for outdoor enthusiasts. Enjoy various water activities, unwind on the beach, and take in the scenic beauty of the surrounding area for a perfect adventure. ### Best time to go to Southold The best time to visit Southold is dependant on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 35.6°F (2.0°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly Low | | February | 35.8°F (2.1°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | March | 39.7°F (4.3°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | April | 47.5°F (8.6°C) | Light Rain | Mostly Sunny | Average | Average | | May | 55.8°F (13.2°C) | Light Rain | Mostly Sunny | Average | Average | | June | 64.9°F (18.3°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High | | July | 73.0°F (22.8°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High | | August | 73.4°F (23.0°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High | | September | 68.2°F (20.1°C) | Light Rain | Mostly Sunny | Average | Average | | October | 59.7°F (15.4°C) | Light Rain | Mostly Sunny | Average | Average | | November | 49.6°F (9.8°C) | Light Rain | Mostly Sunny | Moderately Low | Average | | December | 42.1°F (5.6°C) | Light Rain | Mostly Cloudy | Moderately Low | Average | ### The nearest major airports for your trip to Southold For your visit to Southold, New York, you have several airport options. Islip, NY ([ISP](https://www.expedia.ca/MacArthur-Airport-Hotels.0-aISP-0.Travel-Guide-Filter-Hotels)\-MacArthur) is located 64.4km away, with nearby hotels such as the 3.5-star [Hyatt Regency Long Island](https://www.expedia.ca/Hauppauge-Hotels-Hyatt-Regency-Long-Island.h3668.Hotel-Information), Jake's 58 Casino Hotel, and Radisson Hotel Hauppauge, each offering convenient access to the airport. New Haven, CT ([HVN](https://www.expedia.ca/Tweed-New-Haven-Regional-Airport-Hotels.0-aHVN-0.Travel-Guide-Filter-Hotels)\-Tweed - New Haven Regional) is 45.1km distant, featuring 4-star accommodations like [The Blake Hotel](https://www.expedia.ca/New-Haven-Hotels-The-Blake-Hotel.h32129620.Hotel-Information) and [Graduate by Hilton New Haven](https://www.expedia.ca/New-Haven-Hotels-Graduate-New-Haven.h37200005.Hotel-Information). East Hampton, NY ([HTO](https://www.expedia.ca/East-Hampton-Airport-Hotels.0-aHTO-0.Travel-Guide-Filter-Hotels)) is the closest at 19.3km, with luxurious options such as the 5-star [Mill House Inn](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) and the 4.5-star [Topping Rose House](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information), ensuring a comfortable stay while being near the airport. ## Frequently asked questions ### What is the best area to stay in Southold? > This area is the heart of Southold, offering a blend of historic charm and modern conveniences. You'll find a selection of local shops, eateries, and a relaxed atmosphere. The village green and the historic Southold Presbyterian Church are central landmarks, and it's quite walkable for exploring the local businesses. > > > Couples looking for a relaxing escape will appreciate staying in the village centre. It offers easy access to local vineyards, farm stands, and beaches, allowing for leisurely days of wine tasting and coastal strolls. Many of the guesthouses and boutique hotels here provide a comfortable and private setting. > > > For families, staying near the village centre is also a good option due to its proximity to family-friendly activities. Beaches like Kenney's Beach are a short drive away, offering opportunities for swimming and picnicking. ### What are the best hotels in Southold that travellers recommend? > The Shoals Suites and Slips is a 3.5-star hotel with an outstanding 9.6 rating. Guests frequently compliment the beautiful and clean rooms, the super comfortable beds, and the nice staff who make them feel welcome. The hotel also features a vineyard with a tasting room and offers private winery tours. > > > Another highly recommended option is the 3-star Vine & Sand, which also has a 9.6 rating. This hotel is praised for its lovely rooms, which include premium bedding, Egyptian cotton sheets, and rainfall showerheads. Guests can enjoy a free buffet breakfast. It is conveniently located near the Custer Institute and Observatory, just 0.6 km away. ### What are the best family hotels in Southold? > This 3.5-star hotel, with an impressive 9.6 rating, is an excellent choice for families. Guests consistently praise its clean and new rooms, with the suites often described as beautiful and spacious, featuring super comfortable beds. The staff are noted for being particularly nice and welcoming, ensuring a pleasant stay for all. The hotel also offers cribs free of charge, which is a convenient amenity for those travelling with young children. For adults, there's the added benefit of a vineyard and a winery on-site, offering tasting room experiences, release events, and both private and public tours. The location itself is frequently described as beautiful and great, providing a lovely setting for a family holiday. Find more [child-friendly accommodations in Southold](https://www.expedia.ca/Southold-Hotels-Family-Hotel.0-0-d183719-tFamilyHotel.Travel-Guide-Filter-Hotels) ### What hotels in Southold offer free breakfast? > The 3-star Vine & Sand, with an impressive 9.6 rating, offers a free buffet breakfast daily, which guests really appreciate. This hotel also provides complimentary Wi-Fi and free self-parking, adding to the convenience. Guests have described the rooms as lovely. It is also conveniently located near the Custer Institute and Observatory, just 0.6 kilometres away, and Sannino's Bella Vita Vineyard, which is 1.5 kilometres from the hotel. Find more [hotels with free breakfast in Southold](https://www.expedia.ca/Southold-Hotels-Hotels-With-Free-Breakfast.0-0-d183719-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) ### What are the top pet-friendly hotels in Southold? > This property, with an outstanding 9.6 rating, is superb for those travelling with their beloved canine companions, as it specifically permits dogs. It offers a well-equipped kitchen, a patio, and a secured yard, ensuring both comfort and safety for your pets. Guests also benefit from a deck or lanai, ideal for relaxing outdoors. The Cozy Long Island Escape is conveniently located near the Custer Institute and Observatory, just 1.4 km away, and Horton Lane Beach, a mere 1.7 km distant. See more [pet-friendly hotels in Southold](https://www.expedia.ca/Southold-Hotels-Pet-Friendly-Hotel.0-0-d183719-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) ### What are the best budget hotels in Southold? > The 3-star Vine & Sand, with an exceptional 9.6 rating, offers a fantastic stay with complimentary buffet breakfast and free WiFi. Guests describe the rooms as lovely. It is conveniently located near Custer Institute and Observatory, just 0.6 kilometres away, and Sannino's Bella Vita Vineyard, 1.5 kilometres away. Free self-parking is also available, along with bicycles for guest use. View all [budget hotels in Southold](https://www.expedia.ca/Southold-Hotels-Cheap-Hotels.0-0-d183719-tCheapHotels.Travel-Guide-Filter-Hotels) ### What are the most romantic hotels in Southold for couples? > The 3.5-star Shoals Suites and Slips boasts an impressive 9.6 review rating and offers amenities perfectly suited for couples, including couples dining options and a vineyard on site with a tasting room and private tours. Guests frequently praise its beautiful, clean, and new rooms, the super comfortable beds, and the welcoming staff. Its location is also highly praised, being just 0.7 kilometres from The Old Field Vineyards. See all [romantic hotels in Southold](https://www.expedia.ca/Southold-Hotels-Romantic-Hotel.0-0-d183719-tRomanticHotel.Travel-Guide-Filter-Hotels) ### What are the best hotels in Southold near Custer Institute and Observatory? > The 3-star Vine & Sand, rated 9.6, is an excellent choice, being just 0.6 km from the Custer Institute and Observatory. Guests particularly appreciate the lovely rooms and the convenience of free breakfast, including a free buffet breakfast. Free WiFi and free self-parking are also provided. > > > Another highly-rated option is Cozy Long Island Escape, with a 9.6 rating. This accommodation is 1.4 km from the Custer Institute and Observatory and provides a full kitchen, a patio, and a secured yard, making it ideal for a comfortable stay. It is also 1.7 km from Horton Lane Beach. ### When is the best time to go to Southold? > Late spring offers comfortable temperatures, great for exploring the vineyards and enjoying outdoor activities before the peak summer rush. You'll find most businesses are open, and the roads are less busy, making for a more relaxed experience. > > > Early autumn is also ideal, with cooler temperatures, stunning foliage, and the grape harvest season in full swing. Many wineries host special events during this time. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Southold hotel booking with Expedia? ### How much is the nightly rate at a Southold hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [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 NYC-All Airports ](https://www.expedia.ca/All-Airports-Airport-Hotels.0-aNYC-0.Travel-Guide-Filter-Hotels) - [Bay Point Hotels ](https://www.expedia.ca/Bay-Point-Sag-Harbor-Hotels.0-n553248635976471151-0.Travel-Guide-Filter-Hotels) - [Coecles Harbor Hotels ](https://www.expedia.ca/Coecles-Harbor-Shelter-Island-Hotels.0-n553248635976480820-0.Travel-Guide-Filter-Hotels) - [Hotels near Crescent Beach ](https://www.expedia.ca/Crescent-Beach-Hotels.0-l553248621554204758-0.Travel-Guide-Filter-Hotels) - 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