Title: Shelter Island Houseboats from CA $107 | 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 Houseboats in Shelter Island from CA $107 - ![](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 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) No exact matches found, but these alternatives could be just right ## Recommended hotels in Shelter Island ![Exterior](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c614d2a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/7a155d22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) 9.4/10 Exceptional (78) "Nice decoration, clean amenities, good stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) weihao CA $160 CA $262 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/e3411bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, Private Bathroom | Private kitchen](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/733470c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 2 Double Beds, Non Smoking, Kitchenette](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/a4c86ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio, Private Bathroom (King Size Bed)](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/65285c66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Niantic Inn [](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information) 9.2/10 Wonderful (126) "Easy parking. Walkable dining and to boardwalk. Quaint shopping." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerry CA $110 CA $126 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/11d8806e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/85851742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/c263e1c7.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) ### Motel in Southampton [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) 8.6/10 Excellent (440) "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 $123 CA $159 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/aa464430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/ec2516ce.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) ![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aparthotel in Montauk [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) 9.2/10 Wonderful (1265) "Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Violet CA $192 CA $246 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/89358591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/8fa06225.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) ![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) ### Motel in Culloden Shores [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) 8.4/10 Very good (878) "Really clean and nice location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiara [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/afdef753.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/5cb2e3e0.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 [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) 8.0/10 Very good (1001) "A welcoming place with some nice touches." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/cc53a2c2.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/54000000/53970000/53963000/53962986/6222b412.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) ![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/b432d22f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bentley Hotel Southampton [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) 9.6/10 Exceptional (392) "great cost-effective option; room was very spacious and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Isadora CA $158 CA $181 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/a27d78bb.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) ![Pool](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/b026cb5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/61b6e714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Old Saybrook [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) 7.2/10 Good (460) "🙂" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jared CA $93 CA $107 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/55dd3e1b.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) ![On the beach](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/150849d6.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) ### Apartment in Old Lyme [](https://www.expedia.ca/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information) 10/10 Exceptional (3) "I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lylian CA $105 CA $267 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information) ![](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/c4264a32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/07ec8098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/ae8f0ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/77fe5437.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Guesthouse in The Heights [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information) 9.4/10 Exceptional (79) " This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen CA $144 CA $165 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/f5b274b4.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) ![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 sitting area](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/be26a516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Old Saybrook - Westbrook [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) 7.8/10 Good (1001) "Staff was kind. Easy, comfortable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jake CA $139 CA $160 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![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/f9bec315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 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) ### Motel in Clinton [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) 8.6/10 Excellent (296) "Great staff and clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyler CA $108 CA $124 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/a8d80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/717b3774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/2c9cc7e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harbor Front Inn [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) 8.8/10 Excellent (545) "Awesome stay!!! Great Location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan CA $181 CA $274 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/147e40ed.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) ![Breakfast area](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/ee8b7737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/1bb00541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Riverhead [](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information) 8.4/10 Very good (708) "Couldn't have been easier! The woman at the front desk was warm and welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival. Adorable backyard with seating, too. Super hot water in the shower. Perfect for an impromptu winter getaway. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mahlon [](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/90ac61e4.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) ![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace King | Living area](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/582203a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Shoals Suites and Slips [](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) 9.6/10 Exceptional (227) "Food!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan CA $241 CA $276 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/0a5356ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/765aa668.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) ![Interior](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/f28083b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Hampton Bays [](https://www.expedia.ca/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information) 10/10 Exceptional (1) CA $76 CA $630 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/035b4021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/185a0230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/0bbae525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/f3aa91d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Waterford [](https://www.expedia.ca/Waterford-Hotels-Charming-3-Bedroom-Cottage-With-WiFi.h108765994.Hotel-Information) 10/10 Exceptional (14) "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 $189 CA $420 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Waterford-Hotels-Charming-3-Bedroom-Cottage-With-WiFi.h108765994.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/56b46a8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9b1283d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/df127760.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/003f8776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Long Island East End [](https://www.expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) 9.2/10 Wonderful (1002) "Our room had a great view of the river and marina. we also loved the seating area in the room. Very comfortable" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Helen CA $173 CA $197 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/b4ee006e.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) ![Dining](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/0c11d8f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/a654b98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Clinton [](https://www.expedia.ca/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information) 9.2/10 Wonderful (36) "Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michelle CA $100 CA $249 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/706ae0a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/f1ebef28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/22da4a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/2fdf39bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Montauk [](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information) 9.0/10 Wonderful (202) "Great weekend trip " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy CA $198 CA $367 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.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=2025-12-25&endDate=2025-12-26®ionId=157359&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&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=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=COTTAGE) 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=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=APARTMENT) 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=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=APART_HOTEL) 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=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&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=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&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=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&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-Houseboats.d157359-aaHouseboats.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Houseboats.d157359-aaHouseboats.Travel-Guide-Accommodation) ## Top Shelter Island Hotel Reviews ![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 10/10 Excellent "Yes" [](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 10/10 Excellent "My stay with Saybrook Point Resort & Marina was amazing. Clean room, amazing staff and amenities! I plan to return again!" [](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 10/10 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." [](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 10/10 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!" [](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 10/10 Excellent "Yes! Ease of registration! The staff helped us with dinning suggestions, hotel programs and amenities!" [](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 "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." [](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 10/10 Excellent "Everything was amazing! Friendly service! " [](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 10/10 Excellent "The Spa was wonderful and the staff was attentive and helpful. " [](https://expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a_y.jpg) ### Montauk Manor 10/10 Excellent "Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. " [](https://expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ## Find out more about Shelter Island ## Shelter Island Houseboats information | Number of reviews | 8,710 | | ----------------- | ------------ | | Accommodation | 3 Houseboats | | Lowest Price | CA $107 | | Highest Price | CA $630 | ## Frequently asked questions ### Why book your houseboat in Shelter Island with Expedia? ## 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) - [Cottages in Dering Harbor ](https://www.expedia.ca/Dering-Harbor-Cottages.d553248634998885605-aaCottages.Travel-Guide-Accommodation) - [Dering Harbor Hotels ](https://www.expedia.ca/Dering-Harbor-Hotels.d553248634998885605.Travel-Guide-Hotels) - [Residences in Dering Harbor ](https://www.expedia.ca/Dering-Harbor-Residences.d553248634998885605-aaResidences.Travel-Guide-Accommodation) - [Town of Southold Town Hotels ](https://www.expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Hotel-Destinations) - [Farmstay in East Marion ](https://www.expedia.ca/East-Marion-Agritourism.d6069914-aaAgritourism.Travel-Guide-Accommodation) - [Cabin Rentals in East Marion ](https://www.expedia.ca/East-Marion-Cabins.d6069914-aaCabins.Travel-Guide-Accommodation) - [Hotels with Bar in East Marion ](https://www.expedia.ca/East-Marion-Hotels-Hotels-With-Bar.0-0-d6069914-tHotelswithBar.Travel-Guide-Filter-Hotels) - [East Marion Hotels ](https://www.expedia.ca/East-Marion-Hotels.d6069914.Travel-Guide-Hotels) - [B&B in Fishers Island ](https://www.expedia.ca/Fishers-Island-Bed-And-Breakfast.d1208-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Fishers Island ](https://www.expedia.ca/Fishers-Island-Guest-Houses.d1208-aaGuestHouses.Travel-Guide-Accommodation) - [Inns in Fishers Island ](https://www.expedia.ca/Fishers-Island-Inns.d1208-aaInns.Travel-Guide-Accommodation) - [B&B in Greenport ](https://www.expedia.ca/Greenport-Bed-And-Breakfast.d110728-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Greenport ](https://www.expedia.ca/Greenport-Cabins.d110728-aaCabins.Travel-Guide-Accommodation) - [Adults Only Resorts & in Greenport ](https://www.expedia.ca/Greenport-Hotels-Adults-Only-Resorts.0-0-d110728-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Beach-Hotel.0-0-d110728-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Boutique-Hotel.0-0-d110728-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Cheap-Hotels.0-0-d110728-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Greenport ](https://www.expedia.ca/Greenport-Hotels-Couples-Resorts-Hotels.0-0-d110728-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Lake Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Lake-Hotels.0-0-d110728-tLakeHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Luxury-Hotel.0-0-d110728-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Oceanfront-Hotels.0-0-d110728-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Shopping-Hotel.0-0-d110728-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Spa-Hotel.0-0-d110728-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Greenport ](https://www.expedia.ca/Greenport-Hotels-Waterpark-Hotels.0-0-d110728-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Greenport Hotels ](https://www.expedia.ca/Greenport-Hotels.d110728.Travel-Guide-Hotels) - [Motels in Greenport ](https://www.expedia.ca/Greenport-Motels.d110728-aaMotels.Travel-Guide-Accommodation) - [Hotels near Greenport Station ](https://www.expedia.ca/Greenport-Station-Hotels.d6186190.Travel-Guide-Hotels) - [Beach Hotel Hotels in Greenport West ](https://www.expedia.ca/Greenport-West-Hotels-Beach-Hotel.0-0-d553248635975876381-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Greenport West ](https://www.expedia.ca/Greenport-West-Hotels-Cheap-Hotels.0-0-d553248635975876381-tCheapHotels.Travel-Guide-Filter-Hotels) - [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) - [Motels in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Motels.d154327-aaMotels.Travel-Guide-Accommodation) - [Palaces in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Palaces.d154327-aaPalaces.Travel-Guide-Accommodation) - [Vacation Homes in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Private-Vacation-Homes.d154327-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Townhomes in Sag Harbor ](https://www.expedia.ca/Sag-Harbor-Townhomes.d154327-aaTownhomes.Travel-Guide-Accommodation) - [B&B in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Bed-And-Breakfast.d183716-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Beach-Hotel.0-0-d183716-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Boutique-Hotel.0-0-d183716-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Couples-Resorts-Hotels.0-0-d183716-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [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 Houseboats in Shelter Island on Expedia.com ](https://www.expedia.com/Shelter-Island-Houseboats.d157359-aaHouseboats.Travel-Guide-Accommodation)