Title: 2 Stars Hotels in Shelter Island, New York from CA $115 - Find Cheap Shelter Island Hotels With 2 Stars | Expedia.ca [Shelter Island Travel Guide](https://expedia.ca/Shelter-Island.dx157359)[Hotels in Shelter Island](https://expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island](https://expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)[Flights to Shelter Island](https://expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Things to do in Shelter Island](https://expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)[Shelter Island Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.ca/Shelter-Island.d157359.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by tom owens # 2 Stars Hotels in Shelter Island, New York from CA $115 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Shelter Island 2 Star Hotels Tonight [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-06&endDate=2025-10-07&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-07&endDate=2025-10-08&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Shelter Island 2 Star Hotels ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2.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) ![Honeymoon Room, Jetted Tub](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/5fc9f561.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) ### The Atlantic Hotel Southampton 7.2/10 Good (947) "Very nice staff and great location " CA $162 CA $220 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.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) ![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) ![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 Saybrook Manor 8.0/10 Very good (1004) "Very friendly and helpful staff." CA $112 CA $129 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f.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) ![Garden](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/a7102e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/e78d099b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greenporter Hotel Greenport 9.2/10 Wonderful (260) "Staff was amazing and this hotel is in the perfect location " CA $184 CA $211 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98.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/54000000/53970000/53963000/53962986/1bfd9996.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/ec2d268d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bentley Hotel Southampton Southampton 9.6/10 Exceptional (348) "Return visitor. Great stay." CA $223 CA $255 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/511d84f6.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) ![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) ### Quality Inn Old Saybrook - Westbrook Old Saybrook 7.6/10 Good (1004) "We have stayed there before so have been pleased with it." CA $130 CA $150 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![King Ocean Front | Balcony view](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/d8d28e68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/7a84d66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 10:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/bd8b651c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Blue Hotel Downtown Montauk 9.2/10 Wonderful (152) "It is aperfect no-frills hotel right on the beach at an extremely reasonable price, walkable to great dining, shopping and more" CA $202 CA $231 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/e820e996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/e70cf1f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/34576327.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) ### The Hampton Maid Hampton Bays 9.0/10 Wonderful (667) "Love this place " CA $262 CA $300 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Maid-Motel.h19715959.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, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/50034f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/28534251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/1c109370.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Budget Host East End Hotel in Riverhead Riverhead 6.6/10 (750) "Good price, beds were comfortable, plenty of parking" CA $144 CA $165 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Riverhead-Hotels-Budget-Host-East-End-Hotel-In-Riverhead.h1130479.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/4e86636a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/78e3666a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/8fa06225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/35541bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kenny's Tipperary Inn Culloden Shores 8.4/10 Very good (861) "Love this place. " CA $162 CA $192 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/13000000/12010000/12001200/12001193/7bd2ac6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12010000/12001200/12001193/67609737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/13000000/12010000/12001200/12001193/1443e1dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/13000000/12010000/12001200/12001193/8593ea67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Surf Resort Downtown Montauk 8.4/10 Very good (211) "The view from our balcony was beautiful! We watched whales and dolphins swim by. Hotel is close to restaurants and town and very walkable. Would definitely stay again " CA $170 CA $195 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Montauk-Hotels-Ocean-Surf-Resort.h12001193.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) ![Double Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/374b57af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/7e8d204d.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) ### Liberty Inn Old Saybrook 7.4/10 Good (631) "Well located for getting to the places we wanted to be. This is an older property, but well taken care of and service was very good. I wouldn’t hesitate to stay here again. " CA $112 CA $129 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Old-Saybrook-Hotels-Liberty-Inn.h3004551.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/7564e116.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) ![Property entrance](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/509e7634.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/f90ba663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shorewood Inn Riverhead 8.6/10 Excellent (699) "Close to food n gas station nice modern place " [](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View 2 Queens with Kitchenette | Private kitchen](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/294d9a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View King](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/e47e67f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c614d2a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Offshore Montauk Montauk 9.2/10 Wonderful (56) "Great place." CA $208 CA $398 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/9ab5b9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7bb1af0a.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) ### Clinton Motel Clinton 8.6/10 Excellent (280) "Great staff and clean rooms" CA $109 CA $125 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) ![Seasonal outdoor pool, open 9:00 AM to 8:00 PM, free cabanas](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5ed206f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Penthouse, 2 Queen Beds, Bay View | Living area](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/cd50a48f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/934899a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fishing](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/eb1df3cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayview Resort Hampton Bays 8.8/10 Excellent (447) "Staff was fantastic, room was always clean and the area was perfect! " CA $228 CA $260 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Hampton-Bays-Hotels-Bayview-Resort.h10453825.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/ae918eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/7454864c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/20fb5209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/98ce732d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Vista Resort Amagansett 9.0/10 Wonderful (195) "Lovely short stay! Right on the beautiful beach. Staff were so welcoming and even quickly sent me something I accidentally left behind in the room. Absolutely plan to be back!" CA $187 CA $214 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Amagansett-Hotels-Ocean-Vista-Resort.h9388116.Hotel-Information) ![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/10000000/9630000/9622400/9622352/6bc86eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/10000000/9630000/9622400/9622352/e2b4ce6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 Queen Bed (Upper Level)](https://images.trvl-media.com/lodging/10000000/9630000/9622400/9622352/19012da7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/10000000/9630000/9622400/9622352/f52858af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Resort Inn Downtown Montauk 9.6/10 Exceptional (475) "Great Staff , the pool and property was spotless , great views!." CA $152 CA $196 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Montauk-Hotels-Ocean-Resort-Inn.h9622352.Hotel-Information) ![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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/f4e648ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/39934cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Inn & Suites Old Saybrook Westbrook Old Saybrook 7.2/10 Good (456) "the so-called breakfast was absolute minimum only thing available was make your own waffle" CA $100 CA $115 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) ![Studio Unit Upper Oceanfront 'San Remo' | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lower 2 Bedroom 2 Bath Corner Oceanfront | Living area](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5d8554d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Kitchen, Pool View](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/d576d9e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Kitchen, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/0c1795de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea Crest Resort Amagansett 9.2/10 Wonderful (489) "Perfect location!" CA $239 CA $304 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.Hotel-Information) ![Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/4e100a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's activities](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/949a0d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/a37c2d73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/6142ad8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton's Vacation Inn Hampton Bays 9.0/10 Wonderful (317) "A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street." CA $176 CA $201 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Hampton-Bays-Hotels-Bowens-By-The-Bays.h10211593.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-Shelter-Island-Hotels.s20-0-d157359.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F2Star-Shelter-Island-Hotels.s20-0-d157359.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 Shelter Island. ![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 $363 CA $452 total Nov 5 - Nov 6 includes taxes & fees 9.4/10 Exceptional! (1,014 reviews) [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Harbor Front Inn 209 Front St, Greenport, NY CA $230 CA $332 total Nov 2 - Nov 3 includes taxes & fees 8.6/10 Excellent! (521 reviews) [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Hyatt Place Long Island East End](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hyatt Place Long Island East End 451 East Main Street, Riverhead, NY CA $250 CA $285 total Oct 28 - Oct 29 includes taxes & fees 9/10 Wonderful! (1,000 reviews) [](https://expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) Still don't see what you're looking for? [See all properties in Shelter Island.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F10%2F2025&endDate=08%2F10%2F2025®ionId=157359&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=07%2F10%2F2025&endDate=08%2F10%2F2025®ionId=157359&star=20&star=20&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F10%2F2025&endDate=08%2F10%2F2025®ionId=157359&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F10%2F2025&endDate=08%2F10%2F2025®ionId=157359&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F10%2F2025&endDate=08%2F10%2F2025®ionId=157359&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F10%2F2025&endDate=08%2F10%2F2025®ionId=157359&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 Shelter Island Nestled between Long Island's forks, this serene island offers pristine beaches and kayaking through Mashomack Preserve's coastal wetlands. Rent bikes to explore historic mansions and stop at Sunset Beach for seafood with spectacular evening views across Shelter Bay. [See all hotels in Shelter Island](https://www.expedia.ca/Hotel-Search?startDate=2025-10-20&endDate=2025-10-21&adults=2®ionId=157359) ![](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg?impolicy=fcrop&w=400&h=400&p=1&q=high) Photo by tom owens ## Top Shelter Island Hotel Reviews ![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "Only issue....the refrigerator makes an annoying sound which is amlpified wearing hearing aids" [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Montauk Blue Hotel](//images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e_y.jpg) ### Montauk Blue Hotel 10/10 Excellent "The ocean view from the 2nd floor was beautiful. The area was very walkable, but it was still nice to have a car to explore other areas such as the light house. Room was clean and staff was helpful. " [](https://expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information) ![Offshore Montauk](//images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154_y.jpg) ### Offshore Montauk 10/10 Excellent "The staff is excellent and very accommodating. Great place in a great location. Would stay here again." [](https://expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![The Bentley Hotel Southampton](//images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 10/10 Excellent "Staff and management were very helpful with the room change request. Property was ideal with large rooms and comfort for a quick stay in the hamptons. Great value!" [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ## Find out more about Shelter Island Want to get out of town on the cheap? Thanks to the low rates and great discounts at the top 2 Stars hotels in Shelter Island, Shelter Island 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 Shelter Island 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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[Boutique Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Boutique-Hotel.0-0-d183716-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Couples-Resorts-Hotels.0-0-d183716-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Pet-Friendly-Hotel.0-0-d183716-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Spa-Hotel.0-0-d183716-tSpaHotel.Travel-Guide-Filter-Hotels) - [Shelter Island Heights Hotels](https://www.expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels) - [Resorts in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Resort-Hotels.d183716-aaResortHotels.Travel-Guide-Accommodation) - [Adults Only Resorts & in Silver Beach](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels-Adults-Only-Resorts.0-n553248635976481903-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Silver Beach Hotels](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels.0-n553248635976481903-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Southold](https://www.expedia.ca/Southold-Hotels-Cheap-Hotels.0-0-d183719-tCheapHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Southold](https://www.expedia.ca/Southold-Hotels-Romantic-Hotel.0-0-d183719-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Southold Hotels](https://www.expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels) - [Motels in Southold](https://www.expedia.ca/Southold-Motels.d183719-aaMotels.Travel-Guide-Accommodation) - [Hotels near Sunset Beach](https://www.expedia.ca/Sunset-Beach-Hotels.0-l553248626388141313-0.Travel-Guide-Filter-Hotels) - [The Heights Hotels](https://www.expedia.ca/The-Heights-Shelter-Island-Heights-Hotels.0-n553248635976473534-0.Travel-Guide-Filter-Hotels) - [Hotels near Wades Beach](https://www.expedia.ca/Wades-Beach-Hotels.0-l553248621554204759-0.Travel-Guide-Filter-Hotels) - [Flights to Greenport](https://www.expedia.ca/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights) - [Flights from Southold](https://www.expedia.ca/lp/flights/183719/flights-from-southold) - [Flights from North Haven](https://www.expedia.ca/lp/flights/553248634998589872/flights-from-north-haven) - [Flights from East Marion](https://www.expedia.ca/lp/flights/6069914/flights-from-east-marion) - [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york) - [Visit East Marion](https://www.expedia.ca/East-Marion.dx6069914) - [Visit Pipes Cove](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295) - [Kontokosta Winery](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction) - [Visit North Haven](https://www.expedia.ca/North-Haven.dx553248634998589872) - [Visit Bay Point](https://www.expedia.ca/Sag-Harbor-Bay-Point.dx553248635976471151) - [Shelter Island Heights Vacations](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides) - [Car rental Greenport](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide) - [Things to do in Greenport](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities) - [Things to do in Shelter Island Heights](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities) - [Book 2 Star Hotels in Shelter Island on Expedia.com](https://www.expedia.com/2Star-Shelter-Island-Hotels.s20-0-d157359.Travel-Guide-Filter-Hotels)