Title: 2 Stars Hotels in Southold, New York from CA $104 - Find Cheap Southold Hotels With 2 Stars | Expedia.ca [Southold Travel Guide](https://expedia.ca/Southold.dx183719)[Hotels in Southold](https://expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels)[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)[Things to do in Southold](https://expedia.ca/Things-To-Do-In-Southold.d183719.Travel-Guide-Activities)[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 # 2 Stars Hotels in Southold, New York from CA $104 - ![](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 ## Check availability on Southold 2 Star Hotels Tonight [Jan 11 - Jan 12](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-11&endDate=2026-01-12&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 12 - Jan 13](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-12&endDate=2026-01-13&adults=2&star=20&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&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-23&endDate=2026-01-25&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Southold 2-star hotels ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f.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) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/72f65e39.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 (1,002 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) ![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) ![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) ![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 (1,002 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 $135 CA $155 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.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/54000000/53970000/53963000/53962986/1bfd9996.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) ![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 (419 reviews) "Adorable boutique hotel with charming unique touches. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $166 CA $191 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Sport court](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/ad346ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/b32a156e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/55438f97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/806c49e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Atlantic Hotel [](https://www.expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) Southampton 7.2/10 Good (976 reviews) "Good place to stay in this area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brenda [](https://www.expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.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) ![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) ![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) ### Spark by Hilton Guilford [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) Guilford 8.8/10 Excellent (79 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 $144 CA $166 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/ad0c5cd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed](https://images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/f74fc429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/686b9f5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/18115e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Budget Host East End Hotel in Riverhead [](https://www.expedia.ca/Riverhead-Hotels-Budget-Host-East-End-Hotel-In-Riverhead.h1130479.Hotel-Information) Riverhead 6.6/10 (791 reviews) "Easy check in/out. Room was clean. Nice quiet stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $130 CA $149 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Riverhead-Hotels-Budget-Host-East-End-Hotel-In-Riverhead.h1130479.Hotel-Information) ![Premium Studio Suite](https://images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/12e5dcab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/0f344e92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Single Room](https://images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/1802c026.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Studio Suite](https://images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/8aa4b577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greenview Inn Riverhead [](https://www.expedia.ca/Riverhead-Hotels-Greenview-Inn-Riverhead.h1373980.Hotel-Information) Riverhead 7.4/10 Good (787 reviews) "Nice staff Beautiful & Safe place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cameron [](https://www.expedia.ca/Riverhead-Hotels-Greenview-Inn-Riverhead.h1373980.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) ![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) ![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) ### Hamlet Inn [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) Southampton 8.6/10 Excellent (447 reviews) "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 $120 CA $155 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.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/a27d78bb.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) ### Econo Lodge Inn & Suites Old Saybrook Westbrook [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) Old Saybrook 7.2/10 Good (466 reviews) "All good it met our expectations as a budget hotel. Large clean room bed was comfortable although the pillows were past it. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hilary CA $93 CA $107 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/2d17124a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio, Private Bathroom (King Size Bed)](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/65285c66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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 reviews) "Quiet and warm and clean. Nice touch from Housekeeping too! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $149 CA $171 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.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) ![Reception](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/f90ba663.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/16000000/15250000/15241400/15241380/1bb00541.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 (714 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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/6b467104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/0d39535c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/89db28cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/32676408.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 (1,001 reviews) "Quality hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $149 CA $170 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Riverhead-Hotels-Holiday-Inn-Express-Hotel-Suites-Long-Island-East-End.h1376205.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/9ab5b9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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) ![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 (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 12 - Jan 13 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/7fc14e3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/9f1bca91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/9f64cb2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/e820e996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hampton Maid [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Maid-Motel.h19715959.Hotel-Information) Hampton Bays 9.0/10 Wonderful (688 reviews) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mitchell [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Maid-Motel.h19715959.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/8ac8989f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/d45d7974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/ad4e87dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/f50958a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Liberty Inn [](https://www.expedia.ca/Old-Saybrook-Hotels-Liberty-Inn.h3004551.Hotel-Information) Old Saybrook 7.4/10 Good (640 reviews) "Great little place to stay with friendly staff and clean room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carolan CA $124 CA $142 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Old-Saybrook-Hotels-Liberty-Inn.h3004551.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/32a9a3ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/08314c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/2e44d319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/1e2037a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lamplighter Motel - Clinton, Connecticut [](https://www.expedia.ca/Old-Saybrook-Hotels-Lamplighter-Motel-Clinton.h14708579.Hotel-Information) Clinton 6.4/10 (228 reviews) "Would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) pamela CA $90 CA $104 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Old-Saybrook-Hotels-Lamplighter-Motel-Clinton.h14708579.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/935ed559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c7d19019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c3d8e2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greenporter Hotel [](https://www.expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) Greenport 9.2/10 Wonderful (284 reviews) "Comfy bed hot shower big room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kai [](https://www.expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ![Deluxe Double Room, 1 King Bed, City View](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/96395fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Double Room | Private kitchenette](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/b36c7eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/a206dde5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/f08791bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Bays Hotel on Main [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information) Hampton Bays 7.2/10 Good (69 reviews) "Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/244ffe91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/42c9a535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/98bad297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/7fef8cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tower Inn And Suites Of Guilford - Madison [](https://www.expedia.ca/New-Haven-Hotels-Tower-Inn-And-Suites-Of-Guilford-Madison.h1399998.Hotel-Information) Guilford 7.4/10 Good (237 reviews) "I really enjoy staying here. The family who runs this motel are so nice. I used to live in Guilford and moved out of state. I return to Conn frequently and always stay here. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan B CA $125 CA $143 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/New-Haven-Hotels-Tower-Inn-And-Suites-Of-Guilford-Madison.h1399998.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) ![Terrace/patio](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/82b0f430.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) ### 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 CA $284 CA $373 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Riverhead-Hotels-Aqua-By-American-Beech.h24081913.Hotel-Information) ![](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%2F2Star-Southold-Hotels.s20-0-d183719.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F2Star-Southold-Hotels.s20-0-d183719.Travel-Guide-Filter-Hotels) ## Explore similar 3-star hotels Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Southold. ![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Saybrook Point Resort & Marina 2 Bridge St Old Saybrook CT CA $426 CA $525 total Jan 12 - Jan 13 includes taxes & fees 9.4/10 Exceptional! (1,011 reviews) [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Water's Edge Resort & Spa 1525 Boston Post Road Westbrook CT CA $289 CA $356 total Jan 12 - Jan 13 includes taxes & fees 8.8/10 Excellent! (1,005 reviews) [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![The Sagaponack](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Sagaponack 3720 Montauk Hwy Wainscott NY CA $203 CA $288 total Jan 23 - Jan 24 includes taxes & fees 8.6/10 Excellent! (220 reviews) [](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) Still don't see what you're looking for? [See all properties in Southold.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=12%2F01%2F2026&endDate=13%2F01%2F2026®ionId=183719&star=20) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=12%2F01%2F2026&endDate=13%2F01%2F2026®ionId=183719&star=20&star=20&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=12%2F01%2F2026&endDate=13%2F01%2F2026®ionId=183719&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=12%2F01%2F2026&endDate=13%2F01%2F2026®ionId=183719&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=12%2F01%2F2026&endDate=13%2F01%2F2026®ionId=183719&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=12%2F01%2F2026&endDate=13%2F01%2F2026®ionId=183719&star=20&star=20&amenities=WATER_PARK) 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. ## 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=2026-01-25&endDate=2026-01-26&adults=2®ionId=183719) ![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=899&h=600&p=1&q=high) Photo by Benny Goh ## Top Southold Hotel Reviews ![Hamlet Inn](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38_y.jpg) ### Hamlet Inn 10/10 Excellent "Nice getaway spot in Southampton. Friendly staff. Well situated to may local points of interest. " [](https://expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 10/10 Excellent "The rooms were so nice! Definitely gonna be back!" [](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) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "This hotel is clean and safe. Parking was easy. Rooms are spacious. Staff was friendly. It's not overly fancy but was perfect for a reasonable price. " [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Hampton Bays Hotel on Main](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/e3ee1fa3_y.jpg) ### Hampton Bays Hotel on Main 10/10 Excellent "Loved the 2 bar options on the property." [](https://expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information) ## Find out more about Southold Want to get out of town on the cheap? Thanks to the low rates and great discounts at the top 2 Stars hotels in Southold, Southold you can sneak away on the trip of your dreams with plenty of cash to spare. In addition to the friendly staff and well-maintained surroundings, you’ll find comfortable rooms, complimentary bath products, and quiet sleeping areas, so you can kick back with all the basic conveniences after a long day. Plus, these properties are perfect, if you need a jumping-off point for exploring the local attractions. Several of the best hotels with 2 Stars in Southold are situated just a stone’s throw from both public transportation and the city’s main freeways. Use the travel tools at Expedia.ca to search for options near your favorite neighborhood, find a cheap deal, and book your room. 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