Title: Shelter Island Villas from CA $103 | 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) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 10 - Jul 12](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-07-10&endDate=2026-07-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shelter Island villas ![Exterior](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/92c1b984.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) ![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) ![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 (304 reviews) "I enjoyed my stay at the Clinton Motel. The room had everything I needed for my one night stay. The front desk personnel were helpful and courteous. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) william CA $107 CA $123 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.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, pool umbrellas, 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) ### Hotel in Old Saybrook [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) 7.8/10 Good (1,000 reviews) "nice area and quiet...eat and drink in the same place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael CA $127 CA $146 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.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) ![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) ![Beach nearby](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/2d17124a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Niantic [](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information) 9.2/10 Wonderful (146 reviews) "The cleanliness of our room was impeccable! The Inn is situated perfectly with access to the beach and great restaurants! Loved it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alfred CA $158 CA $182 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.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) ![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) ![Pool](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/b026cb5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/0820f8f7.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 (469 reviews) "The only thing they serve for continental breakfast are waffles and orange juice and coffee very disappointed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Candise CA $92 CA $106 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/855300/855251/de0d8039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855300/855251/2ad4b390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/860000/855300/855251/1928b68a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/860000/855300/855251/744f57e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Old Saybrook [](https://www.expedia.ca/Old-Saybrook-Hotels-Super-8-By-Wyndham-Old-Saybrook.h855251.Hotel-Information) 7.0/10 Good (914 reviews) "Excellent " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $95 CA $113 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Old-Saybrook-Hotels-Super-8-By-Wyndham-Old-Saybrook.h855251.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) ![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) ![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) ### Hotel in Saybrook Manor [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) 8.0/10 Very good (1,001 reviews) "Very welcoming staff. Average accommodations but comfortable and convenient to supermarket. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/32a9a3ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/08314c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/2e44d319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/4dcdf083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Clinton [](https://www.expedia.ca/Old-Saybrook-Hotels-Lamplighter-Motel-Clinton.h14708579.Hotel-Information) 6.4/10 (230 reviews) "Would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) pamela CA $89 CA $103 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Old-Saybrook-Hotels-Lamplighter-Motel-Clinton.h14708579.Hotel-Information) ![Cottage, 2 Bedrooms, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/f0c0c2c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/724b2312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Tent, 1 Queen Bed](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/fe9ed1d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 2 Bedrooms, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/e632266d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Greenport [](https://www.expedia.ca/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information) 8.6/10 Excellent (11 reviews) "great place to stay, clean and quiet....loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darlin CA $315 CA $360 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.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) ![Breakfast area](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/ee8b7737.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) ![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) 8.6/10 Excellent (729 reviews) "We really love the place. It was walking distance from some of the best steaks in Long Island. The staff was so friendly our room could possibly need a new coat of paint rather than that the room was in very good condition." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas [](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/2bfbb5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/885537fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/ed0cd730.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/w3438h2272x6y0-ee61100c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Southampton [](https://www.expedia.ca/Southampton-Hotels-Southampton-Long-Island-Hotel.h7874046.Hotel-Information) 8.6/10 Excellent (208 reviews) "Staff was amazing. The room was very clean. I've stayed here numerous times, even on the night before my wedding as I was married in the Hamptons and I highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martine CA $172 CA $205 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Southampton-Hotels-Southampton-Long-Island-Hotel.h7874046.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) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/5439c990.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) ### Bed & Breakfast in Niantic [](https://www.expedia.ca/Niantic-Hotels-Inn-At-Harbor-Hill-Marina.h1506634.Hotel-Information) 9.4/10 Exceptional (1,001 reviews) "Always a nice stay. Clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shelby CA $246 CA $282 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Niantic-Hotels-Inn-At-Harbor-Hill-Marina.h1506634.Hotel-Information) ![Suite | Terrace/patio](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/c0e58e0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/cd675eea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/82f07910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/c1dea5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bed & Breakfast in Westbrook Center [](https://www.expedia.ca/Old-Saybrook-Hotels-Westbrook-Inn-Bed-And-Breakfast.h35596310.Hotel-Information) 9.8/10 Exceptional (180 reviews) "Delicious breakfast, wonderful service and beautiful accommodations." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth CA $282 CA $314 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Old-Saybrook-Hotels-Westbrook-Inn-Bed-And-Breakfast.h35596310.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/8ac37006.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) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/85851742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/302ae081.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 (460 reviews) "Excellent host & very clean stay! Host was very helpful with info about area & very accommodating!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $147 CA $190 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/9000000/8440000/8439600/8439546/1abb65f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8440000/8439600/8439546/957f09b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds | Terrace/patio](https://images.trvl-media.com/lodging/9000000/8440000/8439600/8439546/9c36d066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/9000000/8440000/8439600/8439546/0657711d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Southampton [](https://www.expedia.ca/Southampton-Hotels-Sea-Haven-Resort-Motel.h8439546.Hotel-Information) 7.8/10 Good (31 reviews) "Great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Douglas CA $153 CA $196 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Southampton-Hotels-Sea-Haven-Resort-Motel.h8439546.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/d45d7974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/f50958a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/ad4e87dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Accessible, Non Smoking](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/773be73b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Old Saybrook [](https://www.expedia.ca/Old-Saybrook-Hotels-Liberty-Inn.h3004551.Hotel-Information) 7.6/10 Good (641 reviews) "Great little place to stay with friendly staff and clean room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carolan CA $122 CA $140 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Old-Saybrook-Hotels-Liberty-Inn.h3004551.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/565c8d39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/51619c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathrobes, slippers, towels](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/383870b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/802040b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bed & Breakfast in Southampton [](https://www.expedia.ca/Southampton-Hotels-Harpoon-House.h36879849.Hotel-Information) 8.4/10 Very good (149 reviews) "Great spot!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keith CA $206 CA $235 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Southampton-Hotels-Harpoon-House.h36879849.Hotel-Information) ![18 bedrooms, premium bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/24c73875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 King Bed, Bathtub, Bay View (Beach Front suite 2)](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/f0863357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 King Bed, Bathtub, Ocean View](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/700c4d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/82b0f430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Riverhead [](https://www.expedia.ca/Riverhead-Hotels-Aqua-By-American-Beech.h24081913.Hotel-Information) 9.4/10 Exceptional (320 reviews) "Loved the space. We stayed in the suite upstairs and it was so spacious. Had a cute sitting area and it was nice and clean. One downside is the access other guests have to the balcony. Anyone can just come up the stairs and look in your windows if the curtains are not closed just right. Customer service was good and we really enjoyed the cute breakfast baskets in the morning. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Latanya [](https://www.expedia.ca/Riverhead-Hotels-Aqua-By-American-Beech.h24081913.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/ab093123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miss Anna James Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/dc6ad011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Katharine Hepburn Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/20c673f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miss Anna James Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/w848h631x48y3-ad11e9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bed & Breakfast in Old Saybrook Center [](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.Hotel-Information) 9.0/10 Wonderful (23 reviews) "Cute B&B, very nice room, check-in worked well" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Isolde CA $415 CA $460 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/56b46a8b.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) ![Lobby](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/6a538e4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Riverhead [](https://www.expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) 9.2/10 Wonderful (1,001 reviews) "Great hotel, clean, walkable area " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lawanne CA $155 CA $177 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/f08791bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 1 King Bed, City View](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/96395fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/ff8b5175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/a206dde5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Hampton Bays [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information) 7.2/10 Good (71 reviews) "Loved the 2 bar options on the property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $194 CA $222 total includes taxes & fees Mar 27 - Mar 28 [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.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=2026-04-05&endDate=2026-04-06®ionId=157359&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style 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=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&lodging=APART_HOTEL) 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=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&lodging=VACATION_HOME) 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=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&lodging=CONDO) 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=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&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=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&lodging=APARTMENT) 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=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&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=2026-06-20&d1=2026-06-20&endDate=2026-06-23&d2=2026-06-23&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-Villas.d157359-aaVillas.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Villas.d157359-aaVillas.Travel-Guide-Accommodation) ## Top Shelter Island Hotel Reviews ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c_y.jpg) ### Sound View Greenport 6/10 Okay "Was ok" [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/b29cbb53_y.jpg) ### Gurney's Montauk Resort & Seawater Spa 8/10 Good "The food was delicious. There was an issue with the pool which will be fixed soon. My big complaint was room location. I am a senior citizen and my room was in the 700's. Many steep stairs to get down to main building. They offered a ride from my room to main building which I had to use because it was just too far to walk in the dark alone. Walking up to my room was not an option. This may be find for a young family but not for me." [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/fc6ee41c_y.jpg) ### Water's Edge Resort & Spa 8/10 Good "Easy" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/2c9cc7e9_y.jpg) ### The Harbor Front Inn 10/10 Excellent "Warm & cozy lobby, friendly front desk staff. Location is IDEAL and 1 minute walk to the restaurants & stores. Even in a side room (not waterfront) you can see the water. The balcony is nice and we had coffee outside & enjoyed the view. " [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8_y.jpg) ### Montauk Manor 10/10 Excellent "Great property " [](https://expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Journey East Hampton](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/52063f27_y.jpg) ### Journey East Hampton 10/10 Excellent "The Journey is always pleasant. Only issue I have regards buisness travelers....no desk in the rooms." [](https://expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.Hotel-Information) ![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/fce2d4ec_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "Our group of 6 girlfriends had an amazing stay at Saybrook Point Resort & Marina. From the moment we arrived, we knew the weekend was going to be very special. The staff was always warm & welcoming. Shoutout to Scott at reception for ensuring a perfect stay! Dinner at Fresh Salt was delicious & the atmosphere was lively. Shuttle into town was a great option. Can’t wait to book another visit!" [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.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 6/10 Okay "My only complaint is the very dim lighting and lack of lighting in the entranceway especially. Otherwise very comfortable and clean." [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Hyatt Place Long Island East End](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/df127760_y.jpg) ### Hyatt Place Long Island East End 10/10 Excellent "Great hotel, clean, walkable area " [](https://expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) ## Find out more about Shelter Island ## Shelter Island Villas information | Number of reviews | 8,545 | | ----------------- | --------- | | Accommodation | 36 Villas | | Lowest Price | CA $103 | | Highest Price | CA $460 | ## Frequently asked questions ### Why book your villa in Shelter Island with Expedia? ### How can I find cheap villas in Shelter Island? ## 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) - 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