Title: Browse the Best Shelter Island Resorts | Expedia.ca [Shelter Island Travel Guide](https://expedia.ca/Shelter-Island.dx157359)[Hotels in Shelter Island](https://expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island](https://expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)[Flights to Shelter Island](https://expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Things to do in Shelter Island](https://expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)[Shelter Island Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.ca/Shelter-Island.d157359.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by tom owens # Search Resort Hotels in Shelter Island ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Shelter Island Resorts ![Exterior](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0.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) ![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) ![Villa, Multiple Beds, Ground Floor (by the Sea) | Beach/ocean view](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/25adc215.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Water's Edge Resort & Spa Westbrook Center 8.8/10 Excellent (1022) "clean and quiet property, great views, amazing staff" CA $304 CA $374 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.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) ![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) ![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) ![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) ### Gurney's Montauk Resort & Seawater Spa Montauk 8.2/10 Very good (669) "Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay. " CA $438 CA $598 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Luxury Cottage, Bay View](https://images.trvl-media.com/lodging/112000000/111720000/111716900/111716867/03c3b3c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Cottage, Bay View | Private spa tub](https://images.trvl-media.com/lodging/112000000/111720000/111716900/111716867/ae0e1a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Cottage, Bay View | Private kitchenette](https://images.trvl-media.com/lodging/112000000/111720000/111716900/111716867/262dab4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/112000000/111720000/111716900/111716867/57ae1cf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Duryea's Sunset Cottages Montauk 10/10 Exceptional (3) "Absolutely beautiful property. Everything was perfect. The staff are amazing. This an incredible place." CA $1,973 CA $2,255 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Montauk-Hotels-Duryeas-Sunset-Cottages.h111716867.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=2025-10-17&endDate=2025-10-18®ionId=157359&adults=2&lodging=HOTEL_RESORT&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-Resort-Hotels.d157359-aaResortHotels.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Resort-Hotels.d157359-aaResortHotels.Travel-Guide-Accommodation) ## Top Shelter Island Hotel Reviews ![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "Only issue....the refrigerator makes an annoying sound which is amlpified wearing hearing aids" [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Montauk Blue Hotel](//images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e_y.jpg) ### Montauk Blue Hotel 10/10 Excellent "The ocean view from the 2nd floor was beautiful. The area was very walkable, but it was still nice to have a car to explore other areas such as the light house. Room was clean and staff was helpful. " [](https://expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information) ![Beachcomber Resort at Montauk](//images.trvl-media.com/lodging/3000000/2220000/2212000/2211971/d4cb08d2_y.jpg) ### Beachcomber Resort at Montauk 10/10 Excellent "Beautiful room right across from the ocean and by town. Definitely go back!" [](https://expedia.ca/Montauk-Hotels-Beachcomber-At-Montauk.h2211971.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 10/10 Excellent "wonderful place only criticism is how far away rooms are from lobby and the rest of the facilities" [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Sea Crest Resort](//images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769_y.jpg) ### Sea Crest Resort 10/10 Excellent "Perfect location!" [](https://expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](//images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 10/10 Excellent "Liked having and using pool. didn't realize there would be a swimming lesson going on at same time. As this was a quick stop over on our way to Bar Harbor, it fit our needs. Since the room was on the street side it was a bit noisy even with fan running all the time. The room was clean and comfortable and we enjoyed the breakfast which was included. " [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Offshore Montauk](//images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154_y.jpg) ### Offshore Montauk 10/10 Excellent "Super clean cut. Would be nice to have some waters in the room" [](https://expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Zey Hotel](//images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg) ### Zey Hotel 10/10 Excellent "Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay." [](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ![Water's Edge Resort & Spa](//images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "Beautiful grounds and quiet private beach" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ## Find out more about Shelter Island ## Shelter Island Resorts information | Number of reviews | | | --- | --- | | Accommodation | Resorts | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - 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) - [Bay Point Hotels](https://www.expedia.ca/Bay-Point-Sag-Harbor-Hotels.0-n553248635976471151-0.Travel-Guide-Filter-Hotels) - 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[Greenport West Hotels](https://www.expedia.ca/Greenport-West-Hotels.d553248635975876381.Travel-Guide-Hotels) - [Adults Only Resorts & in Hay Beach](https://www.expedia.ca/Hay-Beach-Shelter-Island-Hotels-Adults-Only-Resorts.0-n553248635976470037-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Casino Hotels in Hay Beach](https://www.expedia.ca/Hay-Beach-Shelter-Island-Hotels-Casino-Hotel.0-n553248635976470037-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [New York Hotels](https://www.expedia.ca/New-York-Hotels.d178293.Travel-Guide-Hotels) - [Chalets in North Haven](https://www.expedia.ca/North-Haven-Chalets.d553248634998589872-aaChalets.Travel-Guide-Accommodation) - [North Haven Hotels](https://www.expedia.ca/North-Haven-Hotels.d553248634998589872.Travel-Guide-Hotels) - [Residences in North Haven](https://www.expedia.ca/North-Haven-Residences.d553248634998589872-aaResidences.Travel-Guide-Accommodation) - [B&B in Noyack](https://www.expedia.ca/Noyack-Bed-And-Breakfast.d6217344-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Noyack](https://www.expedia.ca/Noyack-Guest-Houses.d6217344-aaGuestHouses.Travel-Guide-Accommodation) - [Noyack Hotels](https://www.expedia.ca/Noyack-Hotels.d6217344.Travel-Guide-Hotels) - [Aparthotels in Orient](https://www.expedia.ca/Orient-Apart-Hotels.d6326191-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Orient](https://www.expedia.ca/Orient-Bed-And-Breakfast.d6326191-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Luxury Hotels in Orient](https://www.expedia.ca/Orient-Hotels-Luxury-Hotel.0-0-d6326191-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Orient Hotels](https://www.expedia.ca/Orient-Hotels.d6326191.Travel-Guide-Hotels) - [Inns in Orient](https://www.expedia.ca/Orient-Inns.d6326191-aaInns.Travel-Guide-Accommodation) - [Resorts in Orient](https://www.expedia.ca/Orient-Resort-Hotels.d6326191-aaResortHotels.Travel-Guide-Accommodation) - [Aparthotels in Sag Harbor](https://www.expedia.ca/Sag-Harbor-Apart-Hotels.d154327-aaApartHotels.Travel-Guide-Accommodation) - [Apartments in Sag Harbor](https://www.expedia.ca/Sag-Harbor-Apartments.d154327-aaApartments.Travel-Guide-Accommodation) - [B&B in Sag Harbor](https://www.expedia.ca/Sag-Harbor-Bed-And-Breakfast.d154327-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Resorts in Sag Harbor](https://www.expedia.ca/Sag-Harbor-Condominium-Resort.d154327-aaCondominiumResort.Travel-Guide-Accommodation) - [Condo Rentals in Sag Harbor](https://www.expedia.ca/Sag-Harbor-Condos.d154327-aaCondos.Travel-Guide-Accommodation) - [Cottages in Sag Harbor](https://www.expedia.ca/Sag-Harbor-Cottages.d154327-aaCottages.Travel-Guide-Accommodation) - [Guest Houses in Sag Harbor](https://www.expedia.ca/Sag-Harbor-Guest-Houses.d154327-aaGuestHouses.Travel-Guide-Accommodation) - [Sag Harbor Hotels](https://www.expedia.ca/Sag-Harbor-Hotels.d154327.Travel-Guide-Hotels) - [Inns in Sag Harbor](https://www.expedia.ca/Sag-Harbor-Inns.d154327-aaInns.Travel-Guide-Accommodation) - [Hotels near Sag Harbor Marine Park](https://www.expedia.ca/Sag-Harbor-Marine-Park-Hotels.0-l6327316-0.Travel-Guide-Filter-Hotels) - 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[Pet-Friendly Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Pet-Friendly-Hotel.0-0-d183716-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Spa-Hotel.0-0-d183716-tSpaHotel.Travel-Guide-Filter-Hotels) - [Shelter Island Heights Hotels](https://www.expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels) - [Resorts in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Resort-Hotels.d183716-aaResortHotels.Travel-Guide-Accommodation) - [Adults Only Resorts & in Silver Beach](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels-Adults-Only-Resorts.0-n553248635976481903-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Silver Beach Hotels](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels.0-n553248635976481903-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Southold](https://www.expedia.ca/Southold-Hotels-Cheap-Hotels.0-0-d183719-tCheapHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Southold](https://www.expedia.ca/Southold-Hotels-Romantic-Hotel.0-0-d183719-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Southold Hotels](https://www.expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels) - [Motels in Southold](https://www.expedia.ca/Southold-Motels.d183719-aaMotels.Travel-Guide-Accommodation) - [Hotels near Sunset Beach](https://www.expedia.ca/Sunset-Beach-Hotels.0-l553248626388141313-0.Travel-Guide-Filter-Hotels) - [The Heights Hotels](https://www.expedia.ca/The-Heights-Shelter-Island-Heights-Hotels.0-n553248635976473534-0.Travel-Guide-Filter-Hotels) - [Hotels near Wades Beach](https://www.expedia.ca/Wades-Beach-Hotels.0-l553248621554204759-0.Travel-Guide-Filter-Hotels) - [Flights to Greenport](https://www.expedia.ca/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights) - [Flights from Southold](https://www.expedia.ca/lp/flights/183719/flights-from-southold) - [Flights from North Haven](https://www.expedia.ca/lp/flights/553248634998589872/flights-from-north-haven) - [Flights from East Marion](https://www.expedia.ca/lp/flights/6069914/flights-from-east-marion) - [Flights from Orient](https://www.expedia.ca/lp/flights/6326191/flights-from-orient) - [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york) - [Visit East Marion](https://www.expedia.ca/East-Marion.dx6069914) - [Visit Pipes Cove](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295) - [Kontokosta Winery](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction) - [Visit North Haven](https://www.expedia.ca/North-Haven.dx553248634998589872) - [Orient Vacations](https://www.expedia.ca/Orient.d6326191.Destination-Travel-Guides) - [Visit Bay Point](https://www.expedia.ca/Sag-Harbor-Bay-Point.dx553248635976471151) - [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) - [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 Resorts in Shelter Island on Expedia.com](https://www.expedia.com/Shelter-Island-Resorts.d157359-aaResorts.Travel-Guide-Accommodation)