Title: Shelter Island Cottages from CA $111 | 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 Shelter Island Cottage Rentals from CA $111 ![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 In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Shelter Island Cottages ![Exterior](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/65eed284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/b4ee006e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/2e009ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/8e3d5f6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1-bedroom cottage with Grove Beach 🏖️ access. Clinton 9.4/10 Exceptional (32) "Loved the overall stay and experience. The private beach access is a bonus" CA $108 CA $261 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Clinton-Hotels-Shalom-Cottage-With-Private-Beach-Rights.h90991445.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/c0b20841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/41a9fc7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/ec09d195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/c5a2aa07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk Waterford 10/10 Exceptional (9) "This listing was perfect for our stay. Close to the water, beautifully styled, and plenty of items to cook and clean.Thanks so much, Erin!" CA $209 CA $451 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Waterford-Hotels-Charming-3-Bedroom-Cottage-With-WiFi.h108765994.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84068900/84068889/49fd1564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/85000000/84070000/84068900/84068889/5f2fc934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/85000000/84070000/84068900/84068889/983fe32e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/85000000/84070000/84068900/84068889/63a7df8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Tiny Home In Niantic East Lyme 10/10 Exceptional (5) "This property is perfect for 2-3 guests and located within short distance to town. The house is well built and very clean. Five Stars" CA $240 CA $473 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Niantic-Hotels-Luxury-Tiny-Home-In-Niantic.h84068889.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/93000000/92890000/92882900/92882804/add9463a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/93000000/92890000/92882900/92882804/b0e14587.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, table tennis](https://images.trvl-media.com/lodging/93000000/92890000/92882900/92882804/1005bb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92890000/92882900/92882804/593c541a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxurious 3 BR Cottage w/ Ocean View Balcony Amagansett 10/10 Exceptional (3) "Had a great weekend. Right on beach. Beautiful." CA $836 CA $1,501 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Amagansett-Hotels-Luxurious-3-BR-Cottage-W-Ocean-View-Balcony.h92882804.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/71856d05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/825be1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/a3e46cd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/e52f4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Driftwood Cottage @ Saybrook Point Marina, 2 King Beds Old Saybrook Center 9.6/10 Exceptional (38) "Great property, would stay here again." CA $343 CA $715 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/65eee158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/51cab21c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/1eb9ef8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/c937e03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town Greenport 10/10 Exceptional (1) "Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!" CA $356 CA $784 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/93000000/92890000/92882900/92882809/e04b5a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, table tennis](https://images.trvl-media.com/lodging/93000000/92890000/92882900/92882809/c8930af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/93000000/92890000/92882900/92882809/60998335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, table tennis](https://images.trvl-media.com/lodging/93000000/92890000/92882900/92882809/c71a1492.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### My Humble Abode 2BR Beachside Home | TennisPoolPKG Amagansett 10/10 Exceptional (1) CA $766 CA $1,398 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Amagansett-Hotels-My-Humble-Abode-2BR-Beachside-Home-TennisPoolPKG.h92882809.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112020000/112018500/112018432/051a149f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112020000/112018500/112018432/74ff05ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112020000/112018500/112018432/35c74c75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112020000/112018500/112018432/24e1a3fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Montauk Waterfront Cottage with Private Spa & Sunset Views Montauk CA $2,246 CA $2,905 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Montauk-Hotels-Luxury-Montauk-Waterfront-Cottage-With-Private-Spa-Sunset-Views.h112018432.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119970000/119966900/119966853/15dd4e72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119970000/119966900/119966853/w917h683x48y0-57e46773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119970000/119966900/119966853/60e9a277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119970000/119966900/119966853/w509h683x258y0-4df3a872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East End Escape Flanders CA $587 CA $767 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Riverhead-Hotels-East-End-Escape.h119966853.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=2025-10-20&endDate=2025-10-21®ionId=157359&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Cottages.d157359-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Cottages.d157359-aaCottages.Travel-Guide-Accommodation) ## Top Shelter Island Hotel Reviews ![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, well maintained property. Our room was clean and comfortable. Definitely want to come back and extend our stay with family and friends. It’s a beautiful escape on the East Coast " [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.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 "We were there 1 night, so i didnt notice shops. But there was a good restaurant across the road." [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![The Sagaponack](//images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg) ### The Sagaponack 10/10 Excellent "I arrived late night for check-in. The staff text arranged for checking me in ahead of time and left a nice breakfast for me for the morning. Thank you!" [](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) ![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) ![Offshore Montauk](//images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154_y.jpg) ### Offshore Montauk 10/10 Excellent "The staff is excellent and very accommodating. Great place in a great location. Would stay here again." [](https://expedia.ca/Montauk-Hotels-The-Offshore.h113578409.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) ## Find out more about Shelter Island ## Shelter Island Cottages information | Number of reviews | 7,659 | | --- | --- | | Accommodation | 228 Cottages | | Lowest Price | CA $111 | | Highest Price | CA $416 | ## 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) - [Coecles Harbor Hotels](https://www.expedia.ca/Coecles-Harbor-Shelter-Island-Hotels.0-n553248635976480820-0.Travel-Guide-Filter-Hotels) - [Hotels near Crescent Beach](https://www.expedia.ca/Crescent-Beach-Hotels.0-l553248621554204758-0.Travel-Guide-Filter-Hotels) - 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[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) - 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[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 Cottages in Shelter Island on Expedia.com](https://www.expedia.com/Shelter-Island-Cottages.d157359-aaCottages.Travel-Guide-Accommodation)