Title: Shelter Island Condominium Resort Rental from CA $115 | 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 # Find and Compare Shelter Island Condo Resort Rentals - ![](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 In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=CONDO_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=CONDO_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=CONDO_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=CONDO_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Shelter Island Condo Resorts No exact matches found, but these alternatives could be just right ## Recommended hotels in Shelter Island ![Property grounds](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/7033cd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, in-room safe, desk, free WiFi](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/24362044.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/312e44f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/f2189685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Work and Play Special! Extended Stay Discount Shelter Island 10/10 Exceptional (52) "The house was amazing ,clean and full of good energy.it had everything we needed for peaceful, relaxing getaway serenity now! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) moshe A. CA $1,009 CA $1,865 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Shelter-Island-Hotels-Work-And-Play-Special-Extended-Stay-Discount-At-A-Hideaway-With-Stellar-Wifi.h39934446.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/72f65e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a48f4b96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/31bd2f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pier Blue Inn Old Saybrook - Essex Saybrook Manor 8.0/10 Very good (1002) "Great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Indoor pool, open 9:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/8ffa2c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/0b15e4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/9aa57818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Old Saybrook - Westbrook Old Saybrook 7.8/10 Good (1003) "It was a nice clean hotel. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Rhona CA $125 CA $144 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/db00678f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/39934cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/f4e648ae.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) ### Econo Lodge Inn & Suites Old Saybrook Westbrook Old Saybrook 7.2/10 Good (459) "🙂" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jared CA $100 CA $115 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/724b2312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/6b9fb589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 1 Bedroom, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/e582d722.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property map](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/9177383b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Fork Cottages & RV Resort Greenport 9.2/10 Wonderful (5) "great place to stay, clean and quiet....loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darlin CA $266 CA $303 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information) ![Ocean View 2 Queens](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c614d2a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View 2 Queens with Kitchenette | Private kitchen](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/294d9a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Offshore Montauk Montauk 9.2/10 Wonderful (67) "Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $163 CA $266 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/37cdbc57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Manor Montauk 9.2/10 Wonderful (1261) "Idillic property, very relaxing, with a wonderful view. We stayed only one night so we did not try the restaurant or the pool but we enjoyed the stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lydia CA $194 CA $249 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/4e86636a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/78e3666a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/35541bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/efe89d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kenny's Tipperary Inn Culloden Shores 8.4/10 Very good (875) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.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) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f2520f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/d45c604d.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) ### Clinton Motel Clinton 8.6/10 Excellent (290) "Clean and neat place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) john CA $109 CA $126 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/dc9e5678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/20957ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/bfb5cc4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Zey Hotel Greenport 9.2/10 Wonderful (287) "Spotless room, wonderfully comfortable bed, beautiful decorating job and the sweetest, nicest front desk person - Jessica, who made us feel welcome!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marina [](https://www.expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/691fdd98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/5b4c06e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker, cookware/dishes/utensils, spices](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/b6de66d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/909788b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stern at Soundview · Beach+Ocean+Sunrise Old Lyme 10/10 Exceptional (3) "Perfect for a weekend beach getaway. Very small but accurately portrayed in the pictures. It was clean and the host was very helpful and responsive. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia C. CA $107 CA $271 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information) ![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/a8d80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/4e8534b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Harbor View Balcony Junior Suite | Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/e407cc6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harbor Front Inn Greenport 8.8/10 Excellent (533) "Awesome stay!!! Great Location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan CA $189 CA $285 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/7564e116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/65f0ee8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/509e7634.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/f90ba663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shorewood Inn Riverhead 8.4/10 Very good (704) "Bed was very comfortable.. staff was very friendly.. loud traffic in AM.. good water pressure.. would stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shelly [](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/04aa4e82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/d096a355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/e77eab74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hamlet Inn Southampton 8.6/10 Excellent (437) "Great weekend stay! staff was super kind and property was beautiful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chyanne CA $144 CA $186 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Standard Studio, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/da242095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, Private Bathroom | Private kitchen](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/c0e14dbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/2d17124a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/a3a48a86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Niantic Inn Niantic 9.0/10 Wonderful (120) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kancheng CA $169 CA $194 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/aeb3a957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/dc0e4dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/4139664c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/1095c0dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Harbor Hill Marina Niantic 9.4/10 Exceptional (1000) "It’s a beautiful inn and location! Our room on the third floor had windows on three sides - views of the river and marina as well as views of Long Island sound. The staff was friendly and helpful! They had some cheese and crackers available in the afternoon, fresh cookies at 7pm (perfect little snack after returning from dinner), not to mention a nice breakfast. Would recommend to anyone looking to get away and enjoy some r&r." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $223 CA $256 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Niantic-Hotels-Inn-At-Harbor-Hill-Marina.h1506634.Hotel-Information) ![Garden Suite King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/efe41897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/22f2b7c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boardwalk Suite | Private kitchen](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/1898cf3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Shoals Suites and Slips Southold 9.6/10 Exceptional (221) "Great quick stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jasmine T CA $233 CA $302 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/10f54062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/f28083b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/b72c2ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/40dd49e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seabreeze #3: Cozy Cottage by the beach Hampton Bays 10/10 Exceptional (1) CA $77 CA $631 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/ec09d195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/c5a2aa07.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) ### Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk Waterford 10/10 Exceptional (12) "The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jorie M. CA $200 CA $436 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Waterford-Hotels-Charming-3-Bedroom-Cottage-With-WiFi.h108765994.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/ec2d268d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/4bbf34cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch Smart TV with cable channels, TV](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/cbe6e5e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bentley Hotel Southampton Southampton 9.6/10 Exceptional (378) "From the front desk receptionist to checking out, everything was perfect. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eileen CA $163 CA $187 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-29®ionId=157359&adults=2&lodging=CONDO_RESORT&sort=RECOMMENDED&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](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=2026-02-12&d1=2026-02-12&endDate=2026-02-15&d2=2026-02-15&lodging=VACATION_HOME) Cottages [](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=2026-02-12&d1=2026-02-12&endDate=2026-02-15&d2=2026-02-15&lodging=COTTAGE) Aparthotels [](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=2026-02-12&d1=2026-02-12&endDate=2026-02-15&d2=2026-02-15&lodging=APART_HOTEL) Apartments [](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=2026-02-12&d1=2026-02-12&endDate=2026-02-15&d2=2026-02-15&lodging=APARTMENT) Condos [](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=2026-02-12&d1=2026-02-12&endDate=2026-02-15&d2=2026-02-15&lodging=CONDO) Villas [](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=2026-02-12&d1=2026-02-12&endDate=2026-02-15&d2=2026-02-15&lodging=VILLA) Houseboats [](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=2026-02-12&d1=2026-02-12&endDate=2026-02-15&d2=2026-02-15&lodging=HOUSE_BOAT) ![](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-Condominium-Resort.d157359-aaCondominiumResort.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Condominium-Resort.d157359-aaCondominiumResort.Travel-Guide-Accommodation) ## Top Shelter Island Hotel Reviews ![Sag Harbor Inn](//images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf_y.jpg) ### Sag Harbor Inn 10/10 Excellent "Great room, with a great view" [](https://expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information) ![The Harbor Front Inn](//images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 10/10 Excellent "Awesome stay!!! Great Location " [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Sea Crest Resort](//images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769_y.jpg) ### Sea Crest Resort 10/10 Excellent "Location. Staff. Space. " [](https://expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.Hotel-Information) ![The Bentley Hotel Southampton](//images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 10/10 Excellent "From the front desk receptionist to checking out, everything was perfect. " [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![The Sagaponack](//images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg) ### The Sagaponack 10/10 Excellent "Great place, wonderful attention to details. Friendly and helpful staff. Comfortable bed. Will be back!" [](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.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 "Well worth upgrading room. Amenities were amazing " [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Saybrook Point Resort & Marina](//images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "Hospitality at its finest! Bed here was beyond comfortable❤️" [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Staff was amazing , room clean view phenomenal " [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Madison Beach Hotel](//images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg) ### Madison Beach Hotel 10/10 Excellent "I can't say enough about our stay at the Madison Beach Hotel. From the moment we arrived we were treated very well. The view from our room was spectacular. It was so peacful sitting on the balconey listening to the waves and the entire property is beautiful. Spent some time in the shops and restaurants downtown. Dinner at the Wharf restaurant was very nice. Highly recommend breakfast at Christy's next door and we had a great lunch/drinks at Aqua in nearby Clinton. We will definitely be booking another stay at this hotel soon." [](https://expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ## Find out more about Shelter Island ## Shelter Island Condo Resorts information | Number of reviews | 8,143 | | --- | --- | | Accommodation | 1 Condo Resorts | | Lowest Price | CA $115 | | Highest Price | CA $1,865 | ## 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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[Things to do in Shelter Island Heights](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities) - [Book Condo Resorts in Shelter Island on Expedia.com](https://www.expedia.com/Shelter-Island-Condominium-Resort.d157359-aaCondominiumResort.Travel-Guide-Accommodation)