Title: Book The Best Hotels in Shelter Island, NY for 2026 from CA $160 - 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) ![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f/central-park-wagner-cove-rustic-gazebo-lake-autumn-new-york-city.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels in Shelter Island, NY from CA $160 - ![](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=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&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=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&amenities=OCEAN_VIEW) 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=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&amenities=POOL) 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=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&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=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&amenities=PETS) 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=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&travelerType=family_friendly) 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=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&lodging=APARTMENT) 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=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&lodging=COTTAGE) 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=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&amenities=WATER_PARK) ## Check prices for these dates Tonight [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shelter Island hotels ![Exterior](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/32a9a3ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/4dcdf083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/2e44d319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/1e2037a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lamplighter Motel - Clinton, Connecticut [](https://www.expedia.ca/Old-Saybrook-Hotels-Lamplighter-Motel-Clinton.h14708579.Hotel-Information) Clinton 6.4/10 (228) "Extremely nice rooms for the price, with fridge and microwave." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven Traveling with partner CA $90 CA $103 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Old-Saybrook-Hotels-Lamplighter-Motel-Clinton.h14708579.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/9ab5b9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7836a152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free cribs/infant beds, rollaway beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/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 (296) "The room was clean. very easy parking" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesse Traveling solo CA $107 CA $124 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/f08791bb.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 [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information) Hampton Bays 7.2/10 Good (69) "The location is excellent, with easy access to Southampton, Bridgehampton, and East Hampton, plus a nearby train station." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Monique Traveling with friends [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/e5f6999f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/98e9a1b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/2a96c58c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/553f589d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Huntting Inn [](https://www.expedia.ca/East-Hampton-Hotels-The-Huntting-Inn.h35373712.Hotel-Information) Egypt Lane Historic District 9.0/10 Wonderful (104) "Staff and management was very welcoming!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sanailer CA $527 CA $616 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/East-Hampton-Hotels-The-Huntting-Inn.h35373712.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/7fc14e3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![40-inch flat-screen TV with digital channels, TV, Netflix](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/9675cf7e.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) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/e820e996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hampton Maid [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Maid-Motel.h19715959.Hotel-Information) Hampton Bays 9.0/10 Wonderful (688) "Everyone was so attentive and super clean room!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) marijke Traveling solo [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Maid-Motel.h19715959.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/d1fe07eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/dde88cf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/8e47f99f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mill House Inn [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) Pantigo Road Historic District 9.0/10 Wonderful (73) "Bed was extremely warm and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) margaret Traveling for leisure CA $413 CA $519 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/d7688cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/32e03a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/3b892c7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/968c61db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Maidstone [](https://www.expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.Hotel-Information) East Hampton 8.0/10 Very good (150) "Rooms are nice just little small for the standard rooms Rate was very competitive" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William Traveling for leisure CA $430 CA $492 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/aa9cc8cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite | Living area](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/1b2ac676.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, body treatments, hot stone massages](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/1782c2d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/6893dda0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Canoe Place Inn and Cottages [](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Inn-And-Cottages.h83519458.Hotel-Information) Hampton Bays 9.8/10 Exceptional (60) "The bed and pillows were so comfy" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaye Traveling for leisure [](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Inn-And-Cottages.h83519458.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/52063f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/93f768d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/ecd1e47d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/7418aad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Journey East Hampton [](https://www.expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.Hotel-Information) East Hampton North 9.0/10 Wonderful (160) "The rooms were very nice, spacious and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah Traveling with family [](https://www.expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.Hotel-Information) ![2 restaurants, American cuisine](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/d3bf1318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/67db121e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/44f578e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Carriage House | Living area](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/6a224301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The 1770 House Restaurant & Inn [](https://www.expedia.ca/East-Hampton-Hotels-The-1770-House-Restaurant-Inn.h1085655.Hotel-Information) East Hampton 9.8/10 Exceptional (161) "Nice, quiet & quaint bed and breakfast near all, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) harvey Traveling with partner CA $345 CA $472 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/East-Hampton-Hotels-The-1770-House-Restaurant-Inn.h1085655.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/4db6535f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/bbbb0bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/6809b461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/d9c11af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Hampton Art House Bed & Breakfast [](https://www.expedia.ca/East-Hampton-Hotels-East-Hampton-Art-House-Bed-Breakfast.h31007589.Hotel-Information) Clearwater Beach 9.6/10 Exceptional (65) "Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dan CA $541 CA $619 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/East-Hampton-Hotels-East-Hampton-Art-House-Bed-Breakfast.h31007589.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/ce84672e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/18d5c2a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/5c1700b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sagaponack [](https://www.expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) Wainscott 8.8/10 Excellent (212) "Very clean and modern, spacious rooms and cute snack/coffee area with free soft drinks etc." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carissa Traveling for leisure CA $209 CA $294 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) ![IPod dock, MP3 dock](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/497076d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/f58e6c21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/f543141b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/5ebf0e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Captain Stannard [](https://www.expedia.ca/Westbrook-Hotels-Captain-Stannard-BB-Country-Inn.h1479959.Hotel-Information) Westbrook Center 9.8/10 Exceptional (259) "The rooms are comfortable and well decorated." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lawrence Traveling solo [](https://www.expedia.ca/Westbrook-Hotels-Captain-Stannard-BB-Country-Inn.h1479959.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/1190496c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/5689ac07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/253d38d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/934c8d81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Canoe Place Waterfront Residences [](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Waterfront-Residences.h109662697.Hotel-Information) Hampton Bays 10/10 Exceptional (1) CA $2,335 CA $2,828 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Waterfront-Residences.h109662697.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/62eddf34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/c1dea5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/520263a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/82f07910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westbrook Inn B&B [](https://www.expedia.ca/Old-Saybrook-Hotels-Westbrook-Inn-Bed-And-Breakfast.h35596310.Hotel-Information) Westbrook Center 9.8/10 Exceptional (175) "And the bed was extremely comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $306 CA $339 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Old-Saybrook-Hotels-Westbrook-Inn-Bed-And-Breakfast.h35596310.Hotel-Information) ![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/028711b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/a3bdf0f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/56f0c16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/06408853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Roundtree, Amagansett [](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.Hotel-Information) Amagansett North 10/10 Exceptional (91) "the grounds on this property are wonderful with clean and comfortable suites" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) adam Traveling with family CA $819 CA $982 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/9000000/8440000/8439600/8439546/96167988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/9000000/8440000/8439600/8439546/48c79f65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8440000/8439600/8439546/957f09b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds | Terrace/patio](https://images.trvl-media.com/lodging/9000000/8440000/8439600/8439546/9c36d066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea Haven Resort Motel [](https://www.expedia.ca/Southampton-Hotels-Sea-Haven-Resort-Motel.h8439546.Hotel-Information) Southampton 7.8/10 Good (31) "Great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Douglas CA $166 CA $213 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Southampton-Hotels-Sea-Haven-Resort-Motel.h8439546.Hotel-Information) ![Miss Anna James Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/w848h631x48y3-ad11e9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Katharine Hepburn Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/20c673f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/f09f38b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miss Anna James Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/dc6ad011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### James Pharmacy Bed & Breakfast [](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.Hotel-Information) Old Saybrook Center 9.0/10 Wonderful (23) "The location was perfect - located near restaurants, shops, and the beach" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel Traveling with partner CA $416 CA $462 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/db00678f.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 (460) "I was pleasantly surprised by how clean and updated the room was." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robin Traveling for leisure CA $92 CA $106 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/565c8d39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/51619c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/802040b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/2ac0e6c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harpoon House [](https://www.expedia.ca/Southampton-Hotels-Harpoon-House.h36879849.Hotel-Information) Southampton 8.4/10 Very good (148) "bed was crisp & comfortable" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DIANE Traveling with friends [](https://www.expedia.ca/Southampton-Hotels-Harpoon-House.h36879849.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=2025-12-27&endDate=2025-12-28®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 - Coecles Harbor - Menantic Creek - Shorewood - Hay Beach [](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=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 Shelter Island Whale's Tail and Gardiner's Bay Country Club, 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 Shelter Island Historical Society and Sunset Beach. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481214) [](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 Mashomack Preserve and Sunset 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=2025-12-27&endDate=2025-12-28&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/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) [](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/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/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) ## More cheap stays in Shelter Island ![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 $139 CA $160 total Jan 8 - Jan 9, 2026 includes taxes & fees 7.6/10 Good! (1,001 reviews) [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Budget Host East End Hotel in Riverhead](https://images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/ad0c5cd3_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Budget Host East End Hotel in Riverhead 30 Lake Avenue Riverhead NY CA $143 CA $164 total Dec 14 - Dec 15 includes taxes & fees 6.6/10 (778 reviews) [](https://expedia.ca/Riverhead-Hotels-Budget-Host-East-End-Hotel-In-Riverhead.h1130479.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 $161 CA $186 total Dec 22 - Dec 23 includes taxes & fees 9.4/10 Exceptional! (391 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=27%2F12%2F2025&endDate=28%2F12%2F2025&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true®ionId=157359) 7.8/10 Good! (1,000 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=27%2F12%2F2025&endDate=28%2F12%2F2025&selected=447803&PinnedHotelID=447803&HadPinnedHotel=true®ionId=157359) 7/10 Good! (974 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=27%2F12%2F2025&endDate=28%2F12%2F2025&selected=105612509&PinnedHotelID=105612509&HadPinnedHotel=true®ionId=157359) 9.2/10 Wonderful! (187 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 275 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 ![Offshore Montauk](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d_y.jpg) ### Offshore Montauk 5/5 Excellent "Excellent views. Quiet and calm " A verified traveller stayed at Offshore Montauk Posted 2 days ago [](https://expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 5/5 Excellent "Yes" A verified traveller stayed at The Harbor Front Inn Posted 5 days ago [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 5/5 Excellent "My stay with Saybrook Point Resort & Marina was amazing. Clean room, amazing staff and amenities! I plan to return again!" A verified traveller stayed at Saybrook Point Resort & Marina Posted 5 days ago [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg) ### Gurney's Montauk Resort & Seawater Spa 5/5 Excellent "EVERYTHING about our stay at Gurneys was wonderful. The staff was outstanding and so accommodating. The room was beautiful looking out at the ocean. We have decided to make a family tradition to go to stay." A verified traveller stayed at Gurney's Montauk Resort & Seawater Spa Posted 5 days ago [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.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 "The staff couldn’t have been nicer! Courteous and caring. The room was immaculate with all necessary amenities. Somewhat dated but not shabby. Very close to town. Parking was ample and right outside my door! I attended a concert at the Kate and did not want to drive an hour home late that evening, so this was perfect for me. Much more reasonable than the other places in the area. Depends on what you’re looking for. Won’t hesitate to come back again!" A verified traveller stayed at Pier Blue Inn Old Saybrook - Essex Posted 6 days ago [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 5/5 Excellent "Yes! Ease of registration! The staff helped us with dinning suggestions, hotel programs and amenities!" A verified traveller stayed at Water's Edge Resort & Spa Posted 6 days ago [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.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 "Had a wonderful stay at The Bentley Hotel Southampton. The room was spacious, stylish, and spotless. I especially loved the record player — such a unique and thoughtful touch that made the stay feel personal and relaxing. The overall vibe of the room and the layout were perfect. Staff were friendly and the property felt well cared for. I’d definitely stay here again and highly recommend it." A verified traveller stayed at The Bentley Hotel Southampton Posted 6 days ago [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![The Sagaponack](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg) ### The Sagaponack 5/5 Excellent "Everything was amazing! Friendly service! " A verified traveller stayed at The Sagaponack Posted 9 days ago [](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) ![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg) ### Madison Beach Hotel 5/5 Excellent "The Spa was wonderful and the staff was attentive and helpful. " A verified traveller stayed at Madison Beach Hotel Posted 11 days ago [](https://expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.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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