Title: Book The Best Hotels in Shelter Island, NY for 2026 from CA $105 - Fully Refundable Options - Expedia.ca [Shelter Island Travel Guide](https://expedia.ca/Shelter-Island.dx157359)[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) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.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 Shelter Island Pool [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-13&d2=2026-02-13&amenities=POOL) Ocean view [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-13&d2=2026-02-13&amenities=OCEAN_VIEW) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-13&d2=2026-02-13&amenities=HOT_TUB) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-13&d2=2026-02-13&amenities=PETS) Spa [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-13&d2=2026-02-13&amenities=SPA_ON_SITE) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-13&d2=2026-02-13&travelerType=family_friendly) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-13&d2=2026-02-13&lodging=COTTAGE) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-13&d2=2026-02-13&lodging=APARTMENT) Waterpark [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-11&d1=2026-02-11&endDate=2026-02-13&d2=2026-02-13&amenities=WATER_PARK) ## Check prices for these dates Tonight [Jan 28 - Jan 29](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-01-28&endDate=2026-01-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 29 - Jan 30](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-01-29&endDate=2026-01-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shelter Island hotels ![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/aa464430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/ec2516ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Manor [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) Montauk 9.2/10 Wonderful (1,287 reviews) "The room was clean and nice. Breakfast was good and the service was great. The pool and Jacuzzi was nice and clean. We would definetly stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Athena CA $167 CA $218 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Ocean View 2 Queens](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![El Presidente | View from room](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/0404b0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/7a155d22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Offshore Montauk [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) Montauk 9.4/10 Exceptional (97 reviews) "Hotel was beautiful !!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $158 CA $258 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.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 (1,003 reviews) "Room was very clean and staff was wonderful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $132 CA $151 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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/afdef753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pier Blue Inn Old Saybrook - Essex [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) Saybrook Manor 8.0/10 Very good (1,000 reviews) "A welcoming place with some nice touches." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/147e40ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/ee8b7737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/cfee764e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/f90ba663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shorewood Inn [](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information) Riverhead 8.4/10 Very good (718 reviews) "ROOM WAS CLEAN, WARM, GOOD PARKING" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JOSEPH [](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information) ![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) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/8ac37006.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 (448 reviews) "Room was in good condition however I found the shower to be extremely small despite having great water pressure and extremely nice temperature." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) gail CA $117 CA $152 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.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) ![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) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/717b3774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harbor Front Inn [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) Greenport 8.8/10 Excellent (563 reviews) "Everything was Great Immaculate hotel very good location sraff was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) latoya CA $171 CA $234 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/dc79a27f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/89358591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kenny's Tipperary Inn [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) Culloden Shores 8.4/10 Very good (885 reviews) "Big room Clean Needs bathroom update In general, we had a good day" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raz [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) ![Resort view](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/55b708b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/ac1b5094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Yoga](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/a7c5a78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sound View Greenport [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) Greenport 8.4/10 Very good (608 reviews) "Nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mateusz CA $173 CA $237 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/9ab5b9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f2520f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free cribs/infant beds, rollaway beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/d1788901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free 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) ### Clinton Motel [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) Clinton 8.6/10 Excellent (301 reviews) "The room was comfortable and clean. A good value for the money." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $103 CA $119 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.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/54000000/53970000/53963000/53962986/6222b412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/4bbf34cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bentley Hotel Southampton [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) Southampton 9.6/10 Exceptional (432 reviews) "Adorable boutique hotel with charming unique touches. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $148 CA $171 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/e3411bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Niantic Inn [](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information) Niantic 9.2/10 Wonderful (137 reviews) "Quiet and warm and clean. Nice touch from Housekeeping too! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $148 CA $170 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/51be5ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/ae8f0ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/c4264a32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/07ec8098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House on Chase Creek [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information) The Heights 9.4/10 Exceptional (80 reviews) "Great stay. The host is amzing and very helpful. The house is peaceful and safe!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marshella CA $142 CA $162 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace King | Living area](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/582203a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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 (238 reviews) "Great stay, will definitely go again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ANTONIO J CA $220 CA $252 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/6a538e4d.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 (1,006 reviews) "Clean and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $152 CA $173 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.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) ![Interior detail](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/885537fe.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) ### 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 $144 CA $172 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Southampton-Hotels-Southampton-Long-Island-Hotel.h7874046.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/81e91eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/6603a689.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/9091cefd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/d9d8edde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech Hotel [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information) Greenport 8.8/10 Excellent (195 reviews) "The property was clean beautiful and pleasant. Loved the trendy decor." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $210 CA $295 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/aeb3a957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/dc0e4dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/4139664c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/5439c990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Harbor Hill Marina [](https://www.expedia.ca/Niantic-Hotels-Inn-At-Harbor-Hill-Marina.h1506634.Hotel-Information) Niantic 9.4/10 Exceptional (1,001 reviews) "Everything was perfect, from the room to the staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $216 CA $249 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Niantic-Hotels-Inn-At-Harbor-Hill-Marina.h1506634.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) ![Pool](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/b026cb5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Inn & Suites Old Saybrook Westbrook [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) Old Saybrook 7.2/10 Good (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 $91 CA $105 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.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) ![Interior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/a206dde5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/ff8b5175.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) ### 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 (70 reviews) "Loved the 2 bar options on the property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $192 CA $220 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.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=2026-02-11&endDate=2026-02-12®ionId=157359&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%2FShelter-Island-Hotels.d157359.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Hotels.d157359.Travel-Guide-Hotels) ## Where to stay in Shelter Island Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. [Learn more about Shelter Island](https://www.expedia.ca/Shelter-Island.dx157359) - Silver Beach - Menantic Creek - Coecles Harbor - Hay Beach - Shorewood ![Center console boat on Long Island, NY. Photographed by drone.](https://images.trvl-media.com/place/553248635976481903/93829460-9892-494c-803a-a3af6b3b8523.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=553248635976481903) ![Silver Beach map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:mzpyF%60vvxLg%60%40kEi%40%7DHuLaYrBOSaK_Oib%40n%40cFuWiStCmEvBXxDwDfHH%7EK%60NpNxDjFyGlHrAf%5CwSlg%40oUhImBpAvPoN%7El%40kp%40dsAcAxK&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=LI215i5nbJyDKLk8XZgKcAhItxY=) ### Silver Beach Silver Beach offers a tranquil coastal retreat on Shelter Island with direct access to the sound. This charming area features weathered cottages and natural shorelines perfect for peaceful waterfront strolls. Shell Beach provides a serene spot for swimming and sunbathing. The neighborhood's calm waters make it ideal for kayaking and small boat activities. Enjoy the scent of salt air mixed with pine and beach roses. Most visitors bring supplies or travel to nearby island markets since Silver Beach maintains its residential character. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481903) ![Welcome To The Beach. Driftwood beach hut with handwritten welcome sign. Port Crescent State Park. Port Austin, Michigan.](https://images.trvl-media.com/place/553248635976481214/0fd5766e-1ec1-4630-87ca-616953333ece.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=553248635976481214) ![Menantic Creek map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:q%7BryFh%7CqxLeOkr%40fT_EnMqEjKc%40fGjBhAuArItErIPrBnB%7DAb%5Cm_AnW&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=wL_I5E54rllE0bcZHkxAdQylRUE=) ### Menantic Creek Menantic Creek on Shelter Island offers a peaceful waterfront escape where natural beauty takes centre stage. This residential haven features classic Hamptons-style homes with private docks nestled among mature trees. The winding creek waters create a tranquil backdrop for a truly authentic island experience. The area provides excellent opportunities for kayaking, paddleboarding, and birdwatching along pristine shorelines. Visitors can easily explore nearby attractions like Wades Beach and Shelter Island Historical Society. Those seeking quiet relaxation will appreciate the gentle creek sounds and salt-tinged air that define this serene coastal retreat. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481214) ![A sweeping view of the natural beauty at Mashomack Preserve on Shelter Island which is situated between the North and South Forks of Long Island, New York.](https://images.trvl-media.com/place/553248635976480820/ef16583d-a1b3-4f29-8d9e-0f21fcceaafc.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=553248635976480820) ![Coecles Harbor map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:ybxyFxymxLw%5Das%40rjAyyBnqA%7Cx%40pIl%7E%40%7DhCnt%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=xFWty9iq-ZDYNo-RgTcjrckcozE=) ### Coecles Harbor Coecles Harbour offers a peaceful retreat where pristine waterfront paths wind along Peconic Bay. Luxury yachts and sailboats dot the protected marina, creating a classic New England coastal scene. Wooden docks extend into calm waters, providing perfect sunset viewing spots. This upscale Shelter Island area balances authentic maritime character with vacation amenities. Visitors can enjoy swimming at Menhadden Lane Beach or explore by kayak and paddleboard. The quiet atmosphere, with only the sounds of lapping waves and seabirds, makes it ideal for those seeking a serene coastal escape. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976480820) ![view of wetland from the Marine Park Salt Marsh Nature Trail in brooklyn, new york (with gil hodges bridge to the rockaways int he background) cloud reflections in bay, water (shell bank creek)](https://images.trvl-media.com/place/553248635976470037/504e907d-021d-4378-950f-32bb724622a2.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=553248635976470037) ![Hay Beach map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:q%7DyyFvxoxLu%7B%40aS%7Ei%40owAnj%40cEfEdc%40a_%40nmA&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=oUw1-B9agSYZdTPReexAj0cx418=) ### Hay Beach Hay Beach offers a tranquil peninsula retreat on Shelter Island, away from the bustling Hamptons scene. This residential haven is surrounded by water on three sides with several beach access points for scenic coastal views. Private waterfront homes and cottages create a peaceful atmosphere where natural beauty takes centre stage. Visitors can explore Menhadden Lane Beach or take short trips to nearby Gardiner's Bay Country Club. The neighborhood's charm lies in its uncrowded shoreline paths and pristine waters. Perfect for kayaking, swimming, and sunset watching, Hay Beach delivers a genuine low-key coastal experience. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976470037) ![Aerial Views of Mamaroneck, New Rochelle, and Larchmont](https://images.trvl-media.com/place/553248635976481937/9210af7b-6de4-447d-b525-19512b2b53b1.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=553248635976481937) ![Shorewood map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:iepyFdhnxLeP%7DEwBi%5Cha%40wNvL%7BLRhb%40cTnSsE%60I&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=qbvaos58sMF0pgaReQcoKBoiPaw=) ### Shorewood Shorewood offers a peaceful retreat on Shelter Island with pristine shorelines and scenic waterfront paths. Classic Hamptons-style cottages with cedar shingles and white trim line the quiet, tree-lined streets. The neighborhood's charm lies in its natural beauty and exclusive residential character. Wades Beach beckons with sandy shores and calm bay waters perfect for swimming and kayaking. Visitors appreciate the minimal tourist crowds and opportunities for stargazing at night. The salt air mingles with pine scents while gentle waves create a soothing natural soundtrack. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481937) ## 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=2026-02-11&endDate=2026-02-12&adults=2®ionId=157359) ![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=900&h=430&p=1&q=high) ### Stay near popular Shelter Island attractions [](https://expedia.ca/Shell-Beach-Hotels.0-l553248621554204761-0.Travel-Guide-Filter-Hotels) ![Colorful pebbles and shells on a beach](https://images.trvl-media.com/place/553248621554204761/5a57054c-a374-4fe2-8982-2385bf184bb1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Shell Beach Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621554204761) [](https://expedia.ca/Wades-Beach-Hotels.0-l553248621554204759-0.Travel-Guide-Filter-Hotels) ![Man watching sailboat on Long Island Sound](https://images.trvl-media.com/place/553248621554204759/ee48f50e-5c27-4bcd-8a17-a99baf567092.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wades Beach Why not spend a carefree afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621554204759) [](https://expedia.ca/Gardiners-Bay-Country-Club-Hotels.0-l6282173-0.Travel-Guide-Filter-Hotels) #### Gardiner's Bay Country Club Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6282173) [](https://expedia.ca/Shelter-Island-Whales-Tail-Hotels.0-l553248621554204762-0.Travel-Guide-Filter-Hotels) #### Shelter Island Whale's Tail You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621554204762) [](https://expedia.ca/Mashomack-Preserve-Hotels.0-l6224462-0.Travel-Guide-Filter-Hotels) #### Mashomack Preserve Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. 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=6224462) [](https://expedia.ca/Shelter-Island-Historical-Society-Hotels.0-l553248635961235094-0.Travel-Guide-Filter-Hotels) #### Shelter Island Historical Society You can spend time studying the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248635961235094) ## More cheap stays in Shelter Island ![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 $127 CA $145 total Jan 29 - Jan 30 includes taxes & fees 6.6/10 (794 reviews) [](https://expedia.ca/Riverhead-Hotels-Budget-Host-East-End-Hotel-In-Riverhead.h1130479.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn Old Saybrook - Westbrook 100 Essex Rd Old Saybrook CT CA $132 CA $151 total Feb 15 - Feb 16 includes taxes & fees 7.6/10 Good! (1,000 reviews) [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Bentley Hotel Southampton 161 Hills Station Rd Southampton NY CA $148 CA $171 total Feb 8 - Feb 9 includes taxes & fees 9.4/10 Exceptional! (431 reviews) [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Pier Blue Inn Old Saybrook - Essex 1430 Boston Post Rd Old Saybrook CT [Get rates](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true®ionId=157359) 7.8/10 Good! (1,002 reviews) [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Atlantic Hotel 1655 County Road 39 Southampton NY [Get rates](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=447803&PinnedHotelID=447803&HadPinnedHotel=true®ionId=157359) 7/10 Good! (978 reviews) [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Montauk Blue Hotel](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Montauk Blue Hotel 108 South Emerson Avenue Montauk NY [Get rates](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=105612509&PinnedHotelID=105612509&HadPinnedHotel=true®ionId=157359) 9.2/10 Wonderful! (188 reviews) [](https://expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information) ## Hotels in Shelter Island 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-Shelter-Island-Hotels.s50-0-d157359.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 58 properties [](https://expedia.ca/4Star-Shelter-Island-Hotels.s40-0-d157359.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 272 properties [](https://expedia.ca/3Star-Shelter-Island-Hotels.s30-0-d157359.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 277 properties [](https://expedia.ca/2Star-Shelter-Island-Hotels.s20-0-d157359.Travel-Guide-Filter-Hotels) ## Find out more about Shelter Island ### Top reasons to visit Shelter Island - **Stunning Beaches:** Shelter Island boasts beautiful beaches like Crescent Beach, perfect for relaxation and ocean views. - **Outdoor Adventures:** Enjoy paddle boarding, windsurfing, and golf amidst the island's natural beauty. - **Rich History:** Explore historic buildings and learn about the island's unique heritage. - **Scenic Boat Tours:** Take a picturesque boat tour to appreciate the stunning coastal scenery. - **Diverse Accommodations:** Choose from pet-friendly and family-oriented stays to suit every traveller's needs. ### Find great hotels near Shelter Island Experience the charm of Shelter Island with a variety of accommodations tailored to meet the needs of every traveller. From pet-friendly options to family-oriented stays, you'll find the perfect lodging for your adventure. Explore the best hotels and luxury accommodations that provide a memorable vacation experience amidst the beautiful surroundings of Shelter Island. - **[Sound View Greenport: ](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)** Nestled 6.4km from Shelter Island, Sound View Greenport is a delightful 3.5-star hotel that combines a business-friendly environment with a family-oriented beach getaway. Guests can enjoy direct access to the pristine beach, perfect for sun-soaked days. The hotel is equipped with essential business amenities, including meeting rooms and conference spaces, ensuring a productive stay for corporate travellers. Families will appreciate thoughtful features such as window guards for children and complimentary cribs, making it a safe and enjoyable destination for all ages. - **[Sag Harbor Inn: ](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)** Located 8.0km from Shelter Island, Sag Harbor Inn offers a sophisticated 3.5-star experience tailored for business travellers. This charming inn provides essential business facilities, including meeting rooms, allowing guests to conduct meetings in a serene setting. The inn's proximity to both the vibrant town of Sag Harbor and the scenic waterfront makes it an appealing choice for those looking to blend work and leisure. The inviting atmosphere and convenient amenities make it a great option for a productive yet relaxing stay. - **[The Harbor Front Inn: ](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)** Situated 4.8km from Shelter Island, The Harbor Front Inn is a welcoming 3.5-star hotel that prides itself on being pet-friendly. Ideal for business travellers who wish to bring their furry companions along, the inn features a pet policy that allows dogs in guest rooms. With a focus on comfort and convenience, guests can enjoy business amenities while also having the flexibility to travel with their pets. The charming waterfront location enhances the appeal, ensuring a delightful retreat for both you and your four-legged friends. ### Where to stay near Shelter Island Discover the charm of Shelter Island, a perfect getaway for outdoor enthusiasts and couples alike. Enjoy stunning ocean views and relaxing beach access at Crescent Beach. Explore the rich history of the area while immersing yourself in its family-friendly atmosphere. Nearby Long Island offers additional excursions and scenic spots, making Shelter Island an ideal base for your vacation adventure. Experience the unique blend of relaxation and exploration that this picturesque destination has to offer. - **[Hamptons: ](https://www.expedia.ca/Hamptons-Hotels.d6056452.Travel-Guide-Hotels)** Located 14.5km from Shelter Island, the Hamptons is a quintessential summer retreat known for its stunning beaches and vibrant atmosphere. This area is particularly popular from June to August, attracting visitors for its romantic seaside charm and outdoor activities. With picturesque golf courses and lively music concerts, the Hamptons offers an array of entertainment options. Local landmarks like beautiful beaches and serene lakes provide the perfect backdrop for relaxation and adventure alike, making it an ideal spot for those looking to soak up the sun and enjoy coastal life. - **[Greenport: ](https://www.expedia.ca/Greenport-Hotels.d110728.Travel-Guide-Hotels)** Only 4.8km away from Shelter Island, Greenport boasts a charming small-town vibe combined with rich maritime history. This city, which sees a spike in visitors from June to August, is perfect for those seeking outdoor adventures, romantic getaways, and beach time. Visitors can enjoy various activities like golfing and attending local music concerts. The nearby family-friendly beaches and event conference venues add to the allure, making Greenport a delightful destination for exploration and fun. - **[Sag Harbor: ](https://www.expedia.ca/Sag-Harbor-Hotels.d154327.Travel-Guide-Hotels)** Just 8.0km from Shelter Island, Sag Harbor is a picturesque village that captures the essence of coastal living. Known for its outdoor attractions and romantic atmosphere, this city experiences peak visitor numbers in the summer months. Visitors can indulge in golfing or even skiing during the winter months. The local beaches and parks offer ample opportunities for relaxation and recreation, making Sag Harbor a charming stop for those looking to immerse themselves in the beauty of the East End. ### Things to do in and around Shelter Island Shelter Island is perfect for outdoor adventures and romantic getaways, offering a variety of activities. Enjoy paddle boarding and windsurfing on its beautiful waters, explore numerous attractions, or take a scenic boat tour. Golf enthusiasts will appreciate the island's golf courses, and there are opportunities for skiing as well. With its stunning beaches and natural beauty, Shelter Island is an ideal destination for a memorable vacation. **Shopping** The [Greenport Farmers' Market](https://www.expedia.ca/Greenport-Farmers-Market-Hotels.0-l553248621532665744-0.Travel-Guide-Filter-Hotels), located 4.8km away, offers a vibrant public market experience with local produce and 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 8.0km away, feature unique clothing and books, perfect for souvenirs. If you're up for a drive, explore further shopping options in nearby towns. **Recreation** [Shelter Island Whale's Tail](https://www.expedia.ca/Shelter-Island-Whales-Tail-Hotels.0-l553248621554204762-0.Travel-Guide-Filter-Hotels) offers a fun-filled mini-golf experience with a family-friendly atmosphere perfect for playful competition. For golf enthusiasts, [Noyac Golf Club](https://www.expedia.ca/Noyac-Golf-Club-Hotels.0-l6064499-0.Travel-Guide-Filter-Hotels) presents a picturesque outdoor course just 9.7km away. [Cedar Point County Park](https://www.expedia.ca/Cedar-Point-County-Park-Hotels.0-l6326834-0.Travel-Guide-Filter-Hotels), located 8.0km away, invites relaxation amidst nature with its tranquil surroundings. **Adventure** Experience the thrill at [Splish Splash Water Park](https://www.expedia.ca/Splish-Splash-Water-Park-Hotels.0-l6173416-0.Travel-Guide-Filter-Hotels), located 37.0km from Shelter Island, with exciting water slides and family fun. Hike the scenic [Walking Dunes Trailhead](https://www.expedia.ca/Walking-Dunes-Trailhead-Hotels.0-l553248633992587102-0.Travel-Guide-Filter-Hotels), 25.7km away, for stunning views. For adrenaline, check out the [Riverhead Raceway](https://www.expedia.ca/Riverhead-Raceway-Hotels.0-l6173429-0.Travel-Guide-Filter-Hotels), 35.4km from Shelter Island, featuring exhilarating motor racing. **Nightlife** Experience the enchanting [Greenport Carousel](https://www.expedia.ca/Greenport-Carousel-Hotels.0-l553248635961252285-0.Travel-Guide-Filter-Hotels), just 4.8km away, for a nostalgic ride under the stars. For a cultural evening, visit [Bay Street Theatre](https://www.expedia.ca/Bay-Street-Theatre-Hotels.0-l6326787-0.Travel-Guide-Filter-Hotels), 8.0km from Shelter Island, which offers a blend of romance and entertainment, perfect for families and couples alike. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Shelter Island To save money on your trip to Shelter Island, consider visiting between January and March when hotel prices are at their lowest. Tuesdays are typically the least expensive days for accommodation. Use Expedia to search for budget-friendly hotels, and don’t forget to check for eco-certified options. Additionally, bundling your hotel with flights and activities can lead to great savings. Explore free local attractions and utilize public transport to keep costs down. Planning your visit during the off-peak season and taking advantage of deals will enhance your experience without breaking the bank. - **The most and least expensive months on average to stay in a hotel:** The hotel pricing in Shelter Island is moderately seasonal. The cheapest months to stay in Shelter Island are January to March, where the prices are moderately lower. This is in comparison to June to August, where prices are moderately higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Shelter Island is Tuesday. The most expensive day to stay in Shelter Island is Saturday. - **Find cheap hotels on Expedia:** Expedia’s search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your search results to display prices from lowest to highest, ensuring you see the most affordable hotels first. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking. - **Consider bundling your trip:** You can save money by combining your Shelter Island hotel reservation with your flights and activities through an Expedia package. ### Find the best attractions in and around Shelter Island Shelter Island offers a perfect blend of outdoor adventures, romantic getaways, and family-friendly experiences. Visitors can enjoy beautiful beaches, explore historic buildings, and relax in urban parks. With a focus on culture and leisure, popular activities include unwinding at sunset beach, making it an ideal destination for those seeking relaxation and exploration. - **[67 Steps Beach: ](https://www.expedia.ca/67-Steps-Beach-Hotels.0-l553248626388140598-0.Travel-Guide-Filter-Hotels)** A picturesque beach located 6.4km from Shelter Island, 67 Steps Beach offers a serene escape with its beautiful shoreline and tranquil vibes. It's the perfect spot for sunbathing, swimming, or simply enjoying the coastal scenery. - **[Gardiner's Bay Country Club: ](https://www.expedia.ca/Gardiners-Bay-Country-Club-Hotels.0-l6282173-0.Travel-Guide-Filter-Hotels)** Situated within Shelter Island, this exceptional golf course provides a unique blend of challenging play and stunning views. Experience a round of golf surrounded by lush landscapes and the refreshing breeze from the bay. - **[Orient Point County Park: ](https://www.expedia.ca/Orient-Point-County-Park-Hotels.0-l553248621532665781-0.Travel-Guide-Filter-Hotels)** Located 12.9km from Shelter Island, this urban park is ideal for families and outdoor enthusiasts. Enjoy scenic trails, picnic spots, and the vibrant atmosphere of the city, making it a great place to unwind and connect with nature. ### Best time to go to Shelter Island The best time to visit Shelter Island is dependant on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average 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 | Average | Moderately Low | | February | 35.8°F (2.1°C) | Light Rain | Mostly Cloudy | Average | Moderately Low | | March | 39.7°F (4.3°C) | Light Rain | Mostly Sunny | Average | Moderately 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 | High | Moderately High | | July | 73.0°F (22.8°C) | Light Rain | Mostly Sunny | High | Moderately High | | August | 73.4°F (23.0°C) | Light Rain | Mostly Sunny | High | Moderately 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 | Low | Average | | November | 49.6°F (9.8°C) | Light Rain | Mostly Sunny | Low | Average | | December | 42.1°F (5.6°C) | Light Rain | Mostly Cloudy | Low | Average | ### The nearest major airports for your trip to Shelter Island To reach Shelter Island, 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 situated 70.8km away, with nearby accommodations like the 3.5-star [Hyatt Regency Long Island](https://www.expedia.ca/Hauppauge-Hotels-Hyatt-Regency-Long-Island.h3668.Hotel-Information) and Jake's 58 Casino Hotel, both 6.4km from the airport, along with the [Radisson Hotel Hauppauge-Long Island](https://www.expedia.ca/Hauppauge-Hotels-Radisson-Hotel-Hauppauge-Long-Island.h10706.Hotel-Information), 14.5km away. 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 51.5km from Shelter Island, offering excellent hotels such as [The Blake Hotel](https://www.expedia.ca/New-Haven-Hotels-The-Blake-Hotel.h32129620.Hotel-Information), [Graduate by Hilton New Haven](https://www.expedia.ca/New-Haven-Hotels-Graduate-New-Haven.h37200005.Hotel-Information), and [Omni New Haven Hotel at Yale](https://www.expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information), all 4.8km from the airport. East Hampton, NY ([HTO](https://www.expedia.ca/East-Hampton-Airport-Hotels.0-aHTO-0.Travel-Guide-Filter-Hotels)) is the closest at 14.5km away, featuring 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), both 4.8km from the airport. ## Recent reviews of Shelter Island hotels ![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 5/5 Excellent "All good. Peyton was very helpful, as well as all the other staff. Beautiful view - snowed in! Thanks. " A verified traveller stayed at Saybrook Point Resort & Marina Posted 1 day ago [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a_y.jpg) ### Montauk Manor 5/5 Excellent "Everyone was perfect for our stay at the Montauk Manor!!! The lobby is beautiful and clean. The staff was friendly and very welcoming. We enjoyed massages with Amy, which I highly recommend. Breakfast was delicious at Monte’s (restaurant in the lobby). We loved our room it was immaculate and had everything we needed for a perfect weekend getaway!! We are looking forward to returning again in the spring. " A verified traveller stayed at Montauk Manor Posted 3 days ago [](https://expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![The Preston House & Hotel](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/1f765cec_y.jpg) ### The Preston House & Hotel 5/5 Excellent "Everyone was very helpful and nice, the room was amazing. Super clean and modern. " A verified traveller stayed at The Preston House & Hotel Posted 3 days ago [](https://expedia.ca/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information) ![Offshore Montauk](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d_y.jpg) ### Offshore Montauk 5/5 Excellent "Clean, excellent service, great amenities, walking distance to the strip. Great value. Only thing was bathroom area was cold as air was seeping in. We stayed during the winter. " A verified traveller stayed at Offshore Montauk Posted 4 days ago [](https://expedia.ca/Montauk-Hotels-The-Offshore.h113578409.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 5/5 Excellent "I have stayed here a number of times, and each time the room has been spotless and smells fresh. The staff is very friendly and always offers to help in some way, whether it's to get the snow off my car or provide bottled water. I will be staying here again!" A verified traveller stayed at Pier Blue Inn Old Saybrook - Essex Posted 5 days ago [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.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 "Room was great. Clean and comfortable. Glad I found this place and will be back. " 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) ![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 5/5 Excellent "From the front desk to the rest of the staff, everyone was very friendly but also very professional and very helpful. I called the front desk about 5 straight times to ask questions I was waiting for the receptionist to e upset ,to my surprise she was laughing it up with me. That alone made my stay great" A verified traveller stayed at Quality Inn Old Saybrook - Westbrook Posted 7 days ago [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 5/5 Excellent "Nice" A verified traveller stayed at The Bentley Hotel Southampton Posted 8 days ago [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Montauk Blue Hotel](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e_y.jpg) ### Montauk Blue Hotel 5/5 Excellent "Great view of sunrise and sunset " A verified traveller from New York stayed at Montauk Blue Hotel Posted 10 days ago [](https://expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information) ## Frequently asked questions ### When is the best time to go to Shelter Island? > During the peak season from June to August, Shelter Island attracts a diverse crowd of travellers, making it an exciting time to experience the community vibe. You'll find plenty of opportunities for outdoor adventures, whether it's kayaking in the calm waters, cycling along the picturesque paths, or simply relaxing on the sandy shores. The long, sunlit days provide ample time for sightseeing and enjoying the island's natural beauty. > > > For those who appreciate a quieter experience, consider visiting in September. The summer crowds begin to dwindle, yet the weather remains pleasantly warm, often still hovering around 22°C. This month also offers a wonderful opportunity to enjoy local events without the hustle and bustle of high season. You can take leisurely walks through the vineyards or indulge in fresh seafood at waterfront restaurants, all while soaking in the stunning autumnal scenery. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Shelter Island hotel booking with Expedia? ### How much is the nightly rate at a Shelter Island 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) - [Hotels near Channing Daughters Winery ](https://www.expedia.ca/Channing-Daughters-Winery-Hotels.0-l6326836-0.Travel-Guide-Filter-Hotels) - 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