Title: Book The Best Hotels in Shelter Island, NY for 2025 from CA $129 - Competitive Prices - 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) ![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels in Shelter Island, NY from CA $129 ![](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 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=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&amenities=SPA_ON_SITE) 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=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&amenities=OCEAN_VIEW) 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=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&amenities=PETS) 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=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&amenities=HOT_TUB) 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=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&amenities=POOL) 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=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&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=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&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=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&lodging=APARTMENT) Condo [](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=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&lodging=CONDO) 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=2025-11-11&d1=2025-11-11&endDate=2025-11-13&d2=2025-11-13&amenities=WATER_PARK) ## Check prices for these dates Tonight [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-28&endDate=2025-10-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 4,703 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a.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) ![Suite, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/37cdbc57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Manor Montauk 9.2/10 Wonderful (1258) "Always excellent, even suring my eleventh stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daryl CA $211 CA $269 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/65651fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/8957afe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/770255ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Saybrook Point Resort & Marina Old Saybrook Center 9.4/10 Exceptional (1004) "Beautiful property, we loved our room, friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Natalie CA $336 CA $421 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Outdoor wedding area](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View One Bedroom Suite](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/d3ce4464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront Two Bedroom Suite | Living area](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/60539ea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's activities](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/5a7a4c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gurney's Montauk Resort & Seawater Spa Montauk 8.2/10 Very good (679) "Unbelievable stay! Staff was very accommodating. Beautiful views. Redone very nicely" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lauren CA $425 CA $581 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/w2880h1079x0y0-f10fe240.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 (961) "Very nice staff and great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Granger CA $144 CA $200 total includes taxes & fees Oct 29 - Oct 30 [](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) ![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) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/72f65e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pier Blue Inn Old Saybrook - Essex Saybrook Manor 8.0/10 Very good (1001) "Always a great stay at Pier Blue. Comfy bed and plenty of room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $112 CA $129 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Deluxe Double Room, 1 King Bed, City View](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/e3ee1fa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/f08791bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Interior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/a206dde5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Bays Hotel on Main Hampton Bays 7.0/10 Good (65) "Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia CA $169 CA $193 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard Double Queen](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/07fb7947.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/00b9aef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/6da50c27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marram Montauk 8.8/10 Excellent (241) "It was an amazing relaxing weekend. We want to come back next year the same weekend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Piera CA $278 CA $445 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, hot tub, steam room, body treatments](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/533d1f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/ccd49f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/5c6281d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Water's Edge Resort & Spa Westbrook Center 8.8/10 Excellent (1011) "We love the stay everything was perfect" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) angelica CA $320 CA $392 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.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) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/9aa57818.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) ### Quality Inn Old Saybrook - Westbrook Old Saybrook 7.8/10 Good (1009) "Everything was good, had a quiet happy stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aishwariya CA $131 CA $150 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![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) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/4e8534b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Harbor View Balcony Junior Suite | Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/e407cc6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/64ea9871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harbor Front Inn Greenport 8.8/10 Excellent (526) "Beautiful view and room. Staff friendly and accommodating. Excellent location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $245 CA $348 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.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) ![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) ![Suite, 1 King Bed](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/74fca349.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) ### The Hampton Maid Hampton Bays 9.0/10 Wonderful (676) "Was so lovely would definitely come back again, very cute clean and safe " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Maria CA $263 CA $300 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Maid-Motel.h19715959.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/dc9e5678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/bfb5cc4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/20957ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Zey Hotel Greenport 9.2/10 Wonderful (282) "Such a cute little hotel. Stayed one night bc we had a wedding in the area. Everything was great - the staff was exceptional." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phyllis CA $368 CA $421 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.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) ![BBQ/picnic area](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6f247566.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 9.4/10 Exceptional (63) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $208 CA $398 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b.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/2000000/1210000/1209400/1209378/1ef9d54f.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/2000000/1210000/1209400/1209378/a4958436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/b8f87b0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Madison Beach Hotel Madison Center 9.4/10 Exceptional (327) "Beautiful hotel ! Great waterviews, staff and restaurant food !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim CA $343 CA $394 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/7a84d66f.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) ### Montauk Blue Hotel Downtown Montauk 9.2/10 Wonderful (174) "The beach view is spectacular the surrounding area has everything you need for a each getaway" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $166 CA $190 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/fc8f49f6.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) ### Ocean Vista Resort Amagansett 9.0/10 Wonderful (198) "Such a beautiful place to stay. Pam at the front was so nice and welcoming. The room was clean it was quiet and everyone was friendly. Love that it has a private beach! Would 10/10 recommend it and deff will be going back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kayla c [](https://www.expedia.ca/Amagansett-Hotels-Ocean-Vista-Resort.h9388116.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/1f765cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/e64d0e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/783d70b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/cd124626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Preston House & Hotel Riverhead 9.8/10 Exceptional (366) "Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nakia CA $251 CA $287 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/04aa4e82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/d096a355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/e77eab74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hamlet Inn Southampton 8.6/10 Excellent (433) "A solid inexpensive stay in the Hamptons. Staff are very accommodating, they helped guide us when there was an upcoming storm. Room was comfortable and clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $143 CA $185 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Indoor pool, 2 outdoor pools](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/c7873724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/5c314659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, beach towels, kayaking, fishing](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/d705542f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Yacht Club Montauk 8.6/10 Excellent (1005) "Wonderful hotel and location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) FIONA CA $211 CA $400 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.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) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/6142ad8a.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) ### Hampton's Vacation Inn Hampton Bays 9.0/10 Wonderful (323) "A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maggie CA $189 CA $216 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Hampton-Bays-Hotels-Bowens-By-The-Bays.h10211593.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=2025-11-11&endDate=2025-11-12®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) - Coecles Harbor - Menantic Creek - Silver Beach - Shorewood - Hay Beach [](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 When in Coecles Harbor, you can plan a visit to Gardiner's Bay Country Club and Sunset Beach, some noteworthy sights in the nearby area. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976480820) [](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 If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Crescent Beach. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481214) [](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 While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481903) [](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 While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Sunset Beach and Crescent Beach. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481937) [](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 might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976470037) ## 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=2025-11-11&endDate=2025-11-12&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/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/Wades-Beach-Hotels.0-l553248621554204759-0.Travel-Guide-Filter-Hotels) #### 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/Shell-Beach-Hotels.0-l553248621554204761-0.Travel-Guide-Filter-Hotels) #### 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/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 ![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 CA $112 CA $129 total Oct 29 - Oct 30 includes taxes & fees 7.8/10 Good! (1,011 reviews) [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.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 $131 CA $150 total Nov 9 - Nov 10 includes taxes & fees 7.6/10 Good! (1,008 reviews) [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.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 CA $166 CA $190 total Nov 9 - Nov 10 includes taxes & fees 9/10 Wonderful! (174 reviews) [](https://expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.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 CA $144 CA $200 total Oct 29 - Oct 30 includes taxes & fees 7/10 Good! (961 reviews) [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.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 $208 CA $238 total Nov 11 - Nov 12 includes taxes & fees 9.4/10 Exceptional! (364 reviews) [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Budget Host East End Hotel in Riverhead](https://images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/ad0c5cd3_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Budget Host East End Hotel in Riverhead 30 Lake Avenue, Riverhead, NY CA $131 CA $150 total Oct 29 - Oct 30 includes taxes & fees 6.6/10 (757 reviews) [](https://expedia.ca/Riverhead-Hotels-Budget-Host-East-End-Hotel-In-Riverhead.h1130479.Hotel-Information) ## Hotels in Shelter Island with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6_w.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/8000000/7040000/7033800/7033726/895004c9_w.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/1000000/40000/38800/38715/5e605108_w.jpg) 3 Star Hotels 274 properties [](https://expedia.ca/3Star-Shelter-Island-Hotels.s30-0-d157359.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_w.jpg) 2 Star Hotels 232 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 ![The Bentley Hotel Southampton](//images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 5/5 Excellent "The staff was beyond helpful and nice, the rooms are huge and clean. Would definitely recommend " A verified traveller stayed at The Bentley Hotel Southampton Posted 19 hours ago [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 5/5 Excellent "Perfect " A verified traveller stayed at The Atlantic Hotel Posted 23 hours ago [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 5/5 Excellent "Beautiful Long Island Sound and sunset views." A verified traveller stayed at Sound View Greenport Posted 23 hours ago [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![The Harbor Front Inn](//images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 5/5 Excellent "Beautiful view and room. Staff friendly and accommodating. Excellent location. " A verified traveller stayed at The Harbor Front Inn Posted 1 day ago [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Montauk Blue Hotel](//images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e_y.jpg) ### Montauk Blue Hotel 5/5 Excellent "Great view of the ocean with nice balcony. " A verified traveller stayed at Montauk Blue Hotel Posted 2 days ago [](https://expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](//images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 5/5 Excellent "Everything was good, had a quiet happy stay." A verified traveller stayed at Quality Inn Old Saybrook - Westbrook Posted 2 days ago [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Zey Hotel](//images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg) ### Zey Hotel 5/5 Excellent "Such a cute little hotel. Stayed one night bc we had a wedding in the area. Everything was great - the staff was exceptional." A verified traveller stayed at Zey Hotel Posted 2 days ago [](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ![Gurney's Montauk Resort & Seawater Spa](//images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg) ### Gurney's Montauk Resort & Seawater Spa 5/5 Excellent "Unbelievable stay! Staff was very accommodating. Beautiful views. Redone very nicely" A verified traveller stayed at Gurney's Montauk Resort & Seawater Spa Posted 2 days ago [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![The Sagaponack](//images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg) ### The Sagaponack 5/5 Excellent "An absolute gem of a place to stay. The rooms are full of character and charm, it’s The Hamptons all the way. Great location, too. " A verified traveller stayed at The Sagaponack Posted 2 days ago [](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) ## Frequently asked questions ### Which hotels in Shelter Island offer the best spa experiences? > For hotel guests seeking a relaxing spa experience in Shelter Island, the [Sunset Beach Hotel](https://www.expedia.ca/Shelter-Island-Hotels-Sunset-Beach-Hotel.h104493980.Hotel-Information)is a highly recommended option. > > > > With a 9.2 rating, the Sunset Beach Hotel offers unique massages directly on the beach, accompanied by champagne service. The rooms feature premium bedding, Frette Italian sheets, bathrobes, and designer toiletries, ensuring a comfortable and luxurious stay. ### How much does a spa hotel in Shelter Island cost? > Enjoy staying in a spa hotel in Shelter Island, with plenty of hotels from CA $129 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during the weekend or around public holidays. ### Is it cheaper to book a spa hotel in Shelter Island with flights as part of a package deal? > Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package. ### Are there any unique spa experiences available in Shelter Island? > Yes, Shelter Island offers unique spa experiences, particularly at The Pridwin Spa and the Shelter Island Retreat. > > > > The Pridwin Spa, located within The Pridwin Hotel, provides a relaxing atmosphere with an extensive massage menu. Guests can enjoy both dry and wet saunas, and the spa's design is inspired by the healing properties of water and the Crescent Beach coastline. They utilise plant-based skincare products, enhancing the wellness experience. > > > > The Shelter Island Retreat also features a spa and wellness centre, where guests can relax on sandy shores or by the outdoor swimming pool in addition to enjoying spa services. ### How can I save on a spa hotel in Shelter Island with Expedia? > Members always get our best prices. Find our best Shelter Island spa hotel deals by joining Expedia's free travel rewards program—[One Key™](https://www.expedia.ca/welcome-one-key). As a member, you can unlock instant savings and member perks when you're logged in to your account. For a spontaneous weekend retreat, discover last-minute offers. ### Can I cancel my spa hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right spa hotel in Shelter Island for you. ### What is the best time of year to stay in a beach hotel in Shelter Island? > The most popular time to stay in a beach hotel on Shelter Island is during July and August. These are the warmest months, with average temperatures ranging from 24°C to 27°C, creating ideal conditions for beach days and swimming in the Atlantic. > > > > During this peak season, the island truly comes alive, with a vibrant setting superb for those seeking a classic summer holiday experience. You'll find beach clubs buzzing and all watersports readily available, from paddleboarding to sailing. It's a fantastic time for families to enjoy the sand and sea, and for couples to relax by the water. Due to the high demand, securing your preferred hotel and restaurant reservations well in advance is highly recommended. > > > > For a slightly more tranquil, yet equally enjoyable, experience, June is a wonderful alternative. The weather is still beautifully warm, with temperatures comfortably in the low 20s, making it excellent for outdoor activities like cycling the island's scenic routes or exploring its nature preserves. ### How can I save on a beach hotel in Shelter Island with Expedia? > With Expedia, you'll unlock our lowest prices by becoming a [One Key™](https://www.expedia.ca/welcome-one-key) member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Shelter Island beach hotels. Typically, booking in advance will help you save on your hotel. If you're feeling spontaneous, check out the [last-minute deals](https://www.expedia.ca/lp/b/vacations/last-minute-deals). ### What beach activities should we do in Shelter Island? > The best beach activities in Shelter Island revolve around its calm waters and natural beauty, making swimming, paddleboarding, and kayaking top choices. > > > > For a relaxing beach day, head to Crescent Beach, also known as Sunset Beach. This is a popular spot on the western side of the island, known for its gentle waves and clear water, making it great for a swim or just lounging on the sand. You'll find amenities nearby, and it's a great place to watch the sun go down. This beach is especially enjoyable for couples looking for a peaceful setting. > > > > Families with children will particularly enjoy Shell Beach. Located on the northern side of the island, its shallow, calm waters are ideal for younger swimmers and offer plenty of opportunities for shell collecting. The lack of strong currents makes it a very nice spot for kids to play in the water. > > > > For those looking for a bit more activity, many beaches, including Crescent Beach and Wades Beach, offer excellent conditions for paddleboarding and kayaking. The protected bays around Shelter Island provide smooth waters, great for exploring the coastline at your own pace. ### Is it cheaper to book flights and a beach hotel in Shelter Island as a package? > Booking a beach hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking a beach vacation package well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package. ### Can I cancel my beach hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. 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[Visit Sag Harbor](https://www.expedia.ca/Sag-Harbor.dx154327) - [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) - [Car rental Orient](https://www.expedia.ca/Car-Rentals-In-Orient.d6326191.Car-Rental-Guide) - [Car rental Sag Harbor](https://www.expedia.ca/Car-Rentals-In-Sag-Harbor.d154327.Car-Rental-Guide) - [Sag Harbor Vacation Rentals](https://www.expedia.ca/Sag-Harbor-Vacation-Rentals.d154327.Travel-Guide-VacationRentals) - [Things to do in Greenport](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities) - [Things to do in Sag Harbor](https://www.expedia.ca/Things-To-Do-In-Sag-Harbor.d154327.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 Hotels in Shelter Island on Expedia.com](https://www.expedia.com/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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