Title: Book The Best Hotels in Southold, NY for 2026 from CA $147 - 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 # Find hotels in Southold, NY from CA $147 - ![](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 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=2026-01-20&d1=2026-01-20&endDate=2026-01-22&d2=2026-01-22&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=2026-01-20&d1=2026-01-20&endDate=2026-01-22&d2=2026-01-22&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=2026-01-20&d1=2026-01-20&endDate=2026-01-22&d2=2026-01-22&amenities=SPA_ON_SITE) 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=2026-01-20&d1=2026-01-20&endDate=2026-01-22&d2=2026-01-22&amenities=POOL) 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=2026-01-20&d1=2026-01-20&endDate=2026-01-22&d2=2026-01-22&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=2026-01-20&d1=2026-01-20&endDate=2026-01-22&d2=2026-01-22&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=2026-01-20&d1=2026-01-20&endDate=2026-01-22&d2=2026-01-22&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=2026-01-20&d1=2026-01-20&endDate=2026-01-22&d2=2026-01-22&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=2026-01-20&d1=2026-01-20&endDate=2026-01-22&d2=2026-01-22&amenities=WATER_PARK) ## Check prices for these dates Tonight [Jan 6 - Jan 7](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-06&endDate=2026-01-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 7 - Jan 8](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-07&endDate=2026-01-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-16&endDate=2026-01-18&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 | Living area](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/582203a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/7f5c2322.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 [](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) Southold 9.4/10 Exceptional (234) "Great stay, will definitely go again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ANTONIO J CA $224 CA $256 total includes taxes & fees Feb 5 - Feb 6 [](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) ![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) ![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) ![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 (13) "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) ![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) ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2.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) ### Spark by Hilton Guilford [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) Guilford 8.8/10 Excellent (77) "The front desk staff were excellent, clean and comfortable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JUstine CA $140 CA $161 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/afdef753.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 (1000) "Staff was courteous, and bed was comfortable. The room hasn't had decor updated for decades. Fine for an overnight if you are just traveling through area for the price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sue [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.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/16000000/15250000/15241400/15241380/1bb00541.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) ![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/cfee764e.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 8.6/10 Excellent (713) "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) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/2c9cc7e9.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) ![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) ![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 (559) "Room and staff were amazing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Manuel CA $185 CA $250 total includes taxes & fees Jan 7 - Jan 8 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Golf](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/c263e1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/85851742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/302ae081.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) ### Hamlet Inn [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) Southampton 8.6/10 Excellent (446) "Great weekend stay! staff was super kind and property was beautiful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chyanne CA $119 CA $154 total includes taxes & fees Jan 7 - Jan 8 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.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) ![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) ![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) ### Clinton Motel [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) Clinton 8.6/10 Excellent (299) "Is good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miguel CA $104 CA $120 total includes taxes & fees Jan 7 - Jan 8 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/db00678f.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) ### 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 (465) "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 $92 CA $106 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.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) ![Lobby](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/6a538e4d.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) ### 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 (1003) "Clean and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $153 CA $175 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.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) ![Restaurant](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/ae8f0ca6.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 (79) " This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen CA $143 CA $163 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/70f0f9b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 King Bed, Bathtub, Ocean View](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/700c4d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 King Bed, Bathtub, Bay View (Beach Front suite 2)](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/f0863357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/82b0f430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aqua by American Beech - Adults Only [](https://www.expedia.ca/Riverhead-Hotels-Aqua-By-American-Beech.h24081913.Hotel-Information) Riverhead 9.4/10 Exceptional (312) "Relaxing stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin [](https://www.expedia.ca/Riverhead-Hotels-Aqua-By-American-Beech.h24081913.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) ![Yoga](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/a7c5a78c.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 8.6/10 Excellent (604) "Nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mateusz CA $210 CA $279 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.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, 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) ![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](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/8ffa2c0d.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 (1003) "The very friendly staff made this stay enjoyable from The beginning. The hotel was very clean and comfy. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Virginia CA $133 CA $153 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.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 lounge](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/75016698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/4908c465.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 (1008) "The places lovely good restaurant. Nice dinner excellent complimentary breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caroline CA $146 CA $166 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/e3411bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 2 Double Beds, Non Smoking, Kitchenette](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/a4c86ff1.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 (133) "Quiet and warm and clean. Nice touch from Housekeeping too! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $158 CA $182 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information) ![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/4848cd3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/w3438h2272x6y0-ee61100c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/885537fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room | Living area](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/0fc29bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southampton Long Island Hotel [](https://www.expedia.ca/Southampton-Hotels-Southampton-Long-Island-Hotel.h7874046.Hotel-Information) Southampton 8.6/10 Excellent (206) "Staff was amazing. The room was very clean. I've stayed here numerous times, even on the night before my wedding as I was married in the Hamptons and I highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martine CA $144 CA $172 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Southampton-Hotels-Southampton-Long-Island-Hotel.h7874046.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) ![Seasonal outdoor pool, open 8:00 AM to 7:30 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/3fa39065.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) ### 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 (1001) "Quality hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $147 CA $168 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Riverhead-Hotels-Holiday-Inn-Express-Hotel-Suites-Long-Island-East-End.h1376205.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) ![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) ![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/54000000/53970000/53963000/53962986/6222b412.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 (417) "Adorable boutique hotel with charming unique touches. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $169 CA $194 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/9000000/8440000/8439600/8439546/96167988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds | Terrace/patio](https://images.trvl-media.com/lodging/9000000/8440000/8439600/8439546/9c36d066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8440000/8439600/8439546/957f09b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/9000000/8440000/8439600/8439546/48c79f65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea Haven Resort Motel [](https://www.expedia.ca/Southampton-Hotels-Sea-Haven-Resort-Motel.h8439546.Hotel-Information) Southampton 7.8/10 Good (31) "Great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Douglas CA $165 CA $211 total includes taxes & fees Jan 8 - Jan 9 [](https://www.expedia.ca/Southampton-Hotels-Sea-Haven-Resort-Motel.h8439546.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=2026-01-20&endDate=2026-01-21®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) ## 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=2026-01-20&endDate=2026-01-21&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 ### Stay near popular Southold attractions [](https://expedia.ca/Sparkling-Pointe-Hotels.0-l6327589-0.Travel-Guide-Filter-Hotels) ![Sparkling Pointe](https://mediaim.expedia.com/destination/2/3f9e84132c7cf86c180b2490717bed52.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Sparkling Pointe 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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6327589) [](https://expedia.ca/Horton-Lane-Beach-Hotels.0-l553248635983992604-0.Travel-Guide-Filter-Hotels) #### Horton Lane Beach 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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248635983992604) [](https://expedia.ca/Croteaux-Vineyards-Hotels.0-l6326852-0.Travel-Guide-Filter-Hotels) #### 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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6326852) [](https://expedia.ca/Corey-Creek-Winery-Hotels.0-l6326844-0.Travel-Guide-Filter-Hotels) #### 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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6326844) [](https://expedia.ca/The-Old-Field-Vineyards-Hotels.0-l6327777-0.Travel-Guide-Filter-Hotels) #### The Old Field Vineyards 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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6327777) [](https://expedia.ca/Sanninos-Bella-Vita-Vineyard-Hotels.0-l6327435-0.Travel-Guide-Filter-Hotels) #### 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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6327435) ## 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 $129 CA $147 total Jan 7 - Jan 8 includes taxes & fees 6.6/10 (786 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 $133 CA $153 total Jan 12 - Jan 13 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 $140 CA $161 total Jan 31 - Feb 1 includes taxes & fees 8.6/10 Excellent! (74 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 $169 CA $194 total Jan 22 - Jan 23 includes taxes & fees 9.4/10 Exceptional! (415 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=20%2F01%2F2026&endDate=21%2F01%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=20%2F01%2F2026&endDate=21%2F01%2F2026&selected=447803&PinnedHotelID=447803&HadPinnedHotel=true®ionId=183719) 7/10 Good! (975 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. ## Recent reviews of Southold hotels ![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 5/5 Excellent "Clean and quiet. " A verified traveller stayed at Hyatt Place Long Island East End Posted 1 day ago [](https://expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) ![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 5/5 Excellent "All was beautiful" A verified traveller stayed at Saybrook Point Resort & Marina Posted 2 days ago [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.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 5/5 Excellent "Quality hotel" A verified traveller from Mount Sinai stayed at Holiday Inn Express Hotel & Suites Long Island-East End by IHG Posted 4 days ago [](https://expedia.ca/Riverhead-Hotels-Holiday-Inn-Express-Hotel-Suites-Long-Island-East-End.h1376205.Hotel-Information) ![Spark by Hilton Guilford](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2_y.jpg) ### Spark by Hilton Guilford 5/5 Excellent "The room was in great shape.The staff was friendly and the location was perfect" A verified traveller stayed at Spark by Hilton Guilford Posted 5 days ago [](https://expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg) ### The Shoals Suites and Slips 5/5 Excellent "The room was much larger than expected, very clean. Perfect location, Melissa at the front desk was very helpful" A verified traveller stayed at The Shoals Suites and Slips Posted 5 days ago [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 5/5 Excellent "Nice place" A verified traveller stayed at Sound View Greenport Posted 6 days ago [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 5/5 Excellent "Great place!" A verified traveller stayed at Water's Edge Resort & Spa Posted 7 days ago [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 5/5 Excellent "Great stay at the Bentley Hotel. Don’t judge it from the exterior appearance. The indoor hallways are nice when the weather is stormy and the inside is very spacious, cozy, clean, well appointed and comfortable. Love the modern vibe. The only thing I didn’t care for was the shower head, it doesn’t have a soft rain like spray, just a very strong pulsing and too high up for shorter people. Over all a great stay, and highly recommend it." A verified traveller stayed at The Bentley Hotel Southampton Posted 7 days ago [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Sag Harbor Inn](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf_y.jpg) ### Sag Harbor Inn 5/5 Excellent "Lovely hotel, very clean and friendly! Definitely going back!" A verified traveller stayed at Sag Harbor Inn Posted 9 days ago [](https://expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Southold with outdoor pools? > In addition to its inviting pool, Vine & Sand provides a range of amenities that enhance the stay for families. Enjoy complimentary breakfast on weekends, and take advantage of free WiFi to stay connected or plan your excursions. The hotel also offers self-parking at no extra cost, making it convenient for those driving to the area. With bicycles available for guests, exploring the beautiful surroundings becomes an enjoyable family activity. ### How much does a hotel with outdoor pool in Southold cost? ### Are there hotels in Southold with outdoor pool cabanas or loungers? > The outdoor pool features beach sun loungers, allowing you to soak up the sun comfortably while enjoying the serene surroundings. Additionally, the hotel provides convenient amenities like free WiFi and complimentary breakfast on weekends, enhancing your stay with quality and value. ### Is it cheaper to book flights and a hotel in Southold as a package? ### How can I save on a hotel in Southold with Expedia? ### Can I cancel my hotel reservation on Expedia? ### When is the best time to go to Southold? > During the peak season, which runs from June to August, Southold comes alive with vibrant tourist activity. Visitors flock to the area for its stunning coastal views and charming small-town atmosphere. This time of year is especially enjoyable for those who appreciate leisurely days spent cycling through scenic vineyards or indulging in fresh seafood at waterfront restaurants, where you can savour the local cuisine while soaking in the sun. > > > For families and couples alike, July offers numerous festivals and events that showcase the best of Southold's culture and community spirit. Whether it's a local art fair or a concert in the park, there's always something happening to enhance your visit. The long days and pleasant evenings provide ample time to explore and relax. > > > If you're looking for a slightly quieter experience, consider planning your trip in September. The weather remains pleasant, with temperatures still hovering around 20 to 24°C, and you'll find that prices for accommodations and activities often drop as the summer crowds disperse. This is a wonderful opportunity to enjoy the area's natural beauty without the hustle and bustle of peak season. ### 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 Rentals - 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) - 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