Title: Book The Best Hotels in Southold, NY for 2026 from CA $122 - 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 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=2026-02-01&d1=2026-02-01&endDate=2026-02-03&d2=2026-02-03&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=2026-02-01&d1=2026-02-01&endDate=2026-02-03&d2=2026-02-03&amenities=OCEAN_VIEW) 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=2026-02-01&d1=2026-02-01&endDate=2026-02-03&d2=2026-02-03&amenities=POOL) 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=2026-02-01&d1=2026-02-01&endDate=2026-02-03&d2=2026-02-03&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=2026-02-01&d1=2026-02-01&endDate=2026-02-03&d2=2026-02-03&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=2026-02-01&d1=2026-02-01&endDate=2026-02-03&d2=2026-02-03&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=2026-02-01&d1=2026-02-01&endDate=2026-02-03&d2=2026-02-03&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=2026-02-01&d1=2026-02-01&endDate=2026-02-03&d2=2026-02-03&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=2026-02-01&d1=2026-02-01&endDate=2026-02-03&d2=2026-02-03&amenities=WATER_PARK) ## Check prices for these dates Tonight [Jan 18 - Jan 19](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-18&endDate=2026-01-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 19 - Jan 20](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-19&endDate=2026-01-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [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) ## 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) ![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) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/7f5c2322.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 (235 reviews) "Great stay, will definitely go again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ANTONIO J CA $217 CA $248 total includes taxes & fees Feb 18 - Feb 19 [](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) ![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) ![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) ### Vine & Sand [](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information) Southold 9.6/10 Exceptional (14 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) ![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) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/174f7a84.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 (82 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 $142 CA $164 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.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) ![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, 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 (1,001 reviews) "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 $124 CA $143 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/31bd2f7b.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) ### 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 (1,001 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) ![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) ![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) ### Sound View Greenport [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) Greenport 8.6/10 Excellent (606 reviews) "Nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mateusz CA $187 CA $253 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.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) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/717b3774.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) ### The Harbor Front Inn [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) Greenport 8.8/10 Excellent (562 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 $164 CA $228 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.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) ![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) ### Shorewood Inn [](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information) Riverhead 8.4/10 Very good (716 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) ![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) ![Sports facility](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/003f8776.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 (1,003 reviews) "Clean and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $163 CA $186 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) ![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) ![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 (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 $120 CA $155 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.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) ![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) ![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) ### 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 $149 CA $170 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) ![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) ![Pool](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/65c6d537.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) ![Lobby](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/75016698.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 $146 CA $167 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.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) ![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) ![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) ![Luxury Suite, 1 King Bed, Bathtub, Ocean View](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/02959975.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 reviews) "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) ![Property amenity](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/b5361d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/f61e65f9.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) ![Banquet hall](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/ff7ccdb3.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 (1,002 reviews) "great place,I loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan CA $153 CA $174 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Riverhead-Hotels-Residence-Inn-By-Marriott-New-York-Long-Island-East-End.h18516036.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 cribs/infant beds, rollaway beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f9bec315.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 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 (300 reviews) "Is good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miguel CA $106 CA $122 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.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 detail](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/2bfbb5cd.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) ### Southampton Long Island Hotel [](https://www.expedia.ca/Southampton-Hotels-Southampton-Long-Island-Hotel.h7874046.Hotel-Information) Southampton 8.6/10 Excellent (206 reviews) "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 $146 CA $174 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Southampton-Hotels-Southampton-Long-Island-Hotel.h7874046.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 (1,001 reviews) "Clean, well maintained stay with a working Gym " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leilani CA $154 CA $176 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Riverhead-Hotels-Hilton-Garden-Inn-Riverhead.h1962521.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) ![Restaurant](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/ae8f0ca6.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 reviews) " 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 $145 CA $166 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/6a60f683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/e64d0e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Suite, 1 King Bed](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/4f1bdda5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/1f765cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Preston House & Hotel [](https://www.expedia.ca/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information) Riverhead 9.8/10 Exceptional (375 reviews) "Very comfortable, clean, well-appointed room with a modern yet cozy feel. We stayed one night for a wedding. Would highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marcia CA $212 CA $243 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.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 (425 reviews) "Adorable boutique hotel with charming unique touches. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $153 CA $176 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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=2026-02-01&endDate=2026-02-02®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=2026-02-01&endDate=2026-02-02&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/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) [](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/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) ## More cheap stays in Southold ![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 $124 CA $143 total Feb 15 - Feb 16 includes taxes & fees 7.6/10 Good! (1,001 reviews) [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![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 $130 CA $149 total Jan 19 - Jan 20 includes taxes & fees 6.6/10 (791 reviews) [](https://expedia.ca/Riverhead-Hotels-Budget-Host-East-End-Hotel-In-Riverhead.h1130479.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 $142 CA $164 total Jan 31 - Feb 1 includes taxes & fees 8.8/10 Excellent! (81 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 $153 CA $176 total Jan 25 - Jan 26 includes taxes & fees 9.4/10 Exceptional! (422 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=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true®ionId=183719) 7.8/10 Good! (1,003 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=01%2F02%2F2026&endDate=02%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. ## Recent reviews of Southold hotels ![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 room and staff" A verified traveller stayed at Water's Edge Resort & Spa Posted 4 days ago [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.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 5/5 Excellent "Front desk staff and cleanliness of room." A verified traveller stayed at Hyatt Place Long Island East End Posted 5 days ago [](https://expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.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 "Clean room and building. Pleasant and efficient staff. Would stay there again." A verified traveller stayed at Spark by Hilton Guilford Posted 6 days ago [](https://expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.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 "Eveything was great, front desk people very nice." A verified traveller stayed at Holiday Inn Express Hotel & Suites Long Island-East End by IHG Posted 6 days ago [](https://expedia.ca/Riverhead-Hotels-Holiday-Inn-Express-Hotel-Suites-Long-Island-East-End.h1376205.Hotel-Information) ![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 5/5 Excellent "The staff was wonderful and the room and views fantastic." A verified traveller stayed at The Harbor Front Inn Posted 6 days ago [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.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 "Friendly staff, area was cleaned " A verified traveller stayed at The Shoals Suites and Slips Posted 6 days ago [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 5/5 Excellent "Staff was very friendly room was clean and comfortable " A verified traveller stayed at The Atlantic Hotel Posted 7 days ago [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.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 5/5 Excellent "Clean environment, wonderful staff, quiet area, restaurants and tanger outlet near by!!" A verified traveller stayed at Residence Inn by Marriott New York Long Island East End Posted 8 days ago [](https://expedia.ca/Riverhead-Hotels-Residence-Inn-By-Marriott-New-York-Long-Island-East-End.h18516036.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 "Perfect ❤️" A verified traveller stayed at Saybrook Point Resort & Marina Posted 10 days ago [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.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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