Title: Browse the Best Shelter Island Resorts from CA $283 | 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) ![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Resort Hotels in Shelter Island from CA $283 - ![](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 ## Check prices for these dates Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-01-23&endDate=2026-01-25&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) ![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) ![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 (1007) "We love the stay everything was perfect" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) angelica CA $225 CA $283 total includes taxes & fees Dec 7 - Dec 8 [](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) ![Oceanfront One Bedroom Suite | Terrace/patio](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/3a4c2dc9.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) ![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 (694) "Beautiful view and accomodations. Enjoyed the bathhouse and hotel amenities" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex CA $330 CA $451 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.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=2025-12-11&endDate=2025-12-12®ionId=157359&adults=2&lodging=HOTEL_RESORT&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_157359) ![](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](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "The room was spotless, spacious and unique. Staff was very friendly and efficient. Amenities are what you need. " [](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) ### The Atlantic Hotel 10/10 Excellent "Great hotel for a quick stay - very friendly staff" [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 10/10 Excellent "Always love staying there when in Greenport. Clean. Central. Quality continental breakfast." [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 10/10 Excellent "Great" [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.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 10/10 Excellent "Staff is fantastic " [](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 10/10 Excellent "EXCELLENT staff ! Room was clean. Will stay again " [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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 10/10 Excellent "Great resort with a beautiful restaurant " [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Montauk Blue Hotel](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e_y.jpg) ### Montauk Blue Hotel 10/10 Excellent "I always have a 5/5 stay at Montauk Blue. " [](https://expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information) ![Bayview Resort](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5ed206f2_y.jpg) ### Bayview Resort 10/10 Excellent "Just right. " [](https://expedia.ca/Hampton-Bays-Hotels-Bayview-Resort.h10453825.Hotel-Information) ## Find out more about Shelter Island ## Shelter Island Resorts information | Number of reviews | 1,701 | | --- | --- | | Accommodation | 14 Resorts | | Lowest Price | CA $283 | | Highest Price | CA $451 | ## Frequently asked questions ### What is Shelter Island like for a resort vacation? > Longing for a relaxing getaway? Treat yourself to the comforts and luxuries of a resort, where you can find everything you want for your trip from tasty food and drink options to activities and shopping. Browse the resort options in the area and discover the right one for you, whether you picture yourself sitting down to fine dining or hitting the golf course for an afternoon game. ### What's a favorite resort in Shelter Island? > Here are our top-rated resorts around Shelter Island: [Gurney's Montauk Resort & Seawater Spa](https://www.expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) - Beach resort. 18.4 mi (29.7 km) from Shelter Island. Features 2 restaurants, a private beach, and a full-service spa. [Water's Edge Resort & Spa](https://www.expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) - Beach resort. 15.6 mi (25.1 km) from Shelter Island. Has 3 restaurants, a private beach, and a full-service spa. Highly rated for its great beach location. [Brand New Waterfront - Chic & Sophisticated Unit # 702](https://www.expedia.ca/Montauk-Hotels-Brand-New-Waterfront-Chic-Sophisticated-Unit-702.h96385564.Hotel-Information) - 20.8 mi (33.5 km) from Shelter Island. Enjoy the fitness center and garden. [Duryea's Sunset Cottages](https://www.expedia.ca/Montauk-Hotels-Duryeas-Sunset-Cottages.h111716867.Hotel-Information) - 19.9 mi (32.1 km) from Shelter Island. Amenities include a private beach, free self parking, and a hot tub. [Brand New Waterfront - Chic & Sophisticated](https://www.expedia.ca/Montauk-Hotels-Brand-New-Waterfront-Chic-Sophisticated.h96385607.Hotel-Information) - 20.8 mi (33.5 km) from Shelter Island. Access to a fitness center and a garden. ### What can I do in Shelter Island? > Grab your golf clubs for a game at Gardiner's Bay Country Club, or bring the kids to Shelter Island Whale's Tail for some family fun. For more to see in the area, you can spend time at Sunset Beach or Crescent Beach. ### What's the weather like in Shelter Island? > The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Shelter Island is 57 inches. ### What's the best way to get to and around Shelter Island? > Fly into East Hampton, NY (HTO), which is located 8.8 mi (14.2 km) away from the city center. You can also search for flights into Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.1 km) away. 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[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)