Title: 4 Stars Hotels in Shelter Island, New York from CA $382 - Find Cheap Shelter Island Hotels With 4 Stars | 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 # 4 Stars Hotels in Shelter Island, New York from CA $382 ![](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 availability on Shelter Island 4 Star Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-14&endDate=2025-10-15&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-15&endDate=2025-10-16&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Shelter Island 4 Star Hotels ![Indoor pool, 2 outdoor pools](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/c7873724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, beach towels, kayaking, fishing](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/d705542f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/f58691c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Yacht Club Montauk 8.6/10 Excellent (1003) "Wonderful hotel and location " CA $262 CA $459 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/4c9856c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/55b708b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/f76cf168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sound View Greenport Greenport 8.4/10 Very good (579) "Loved everything about my stay at the Sound view !! " CA $314 CA $427 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Outdoor wedding area](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View One Bedroom Suite](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/d3ce4464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront Two Bedroom Suite | Living area](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/60539ea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront One Bedroom Suite | Terrace/patio](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/3a4c2dc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gurney's Montauk Resort & Seawater Spa Montauk 8.2/10 Very good (671) "Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay. " CA $375 CA $512 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/6da50c27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/b1a067ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/00b9aef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marram Montauk 8.8/10 Excellent (235) "It was an amazing relaxing weekend. We want to come back next year the same weekend!" CA $279 CA $447 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/w2881h1827x0y0-498cd175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed with Sofa bed, Balcony, Bay View (Harbor Loft Suite - Water View)](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/fd2c67f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Village King Room](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/df08158f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Designer toiletries, hair dryer, bathrobes, towels](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/6d1902d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Faraway Sag Harbor Sag Harbor 9.0/10 Wonderful (291) "staff seemed tired and fed up of people staying!" [](https://www.expedia.ca/Sag-Harbor-Hotels-Barons-Cove.h1148848.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/fa5a1a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/75893d43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/ad990fb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/988fd965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Pridwin Hotel Shelter Island Heights 9.6/10 Exceptional (82) "Clean room excellent staff" CA $479 CA $602 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/acd2c1de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/a84ab4fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/7c3abc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/c353f8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Journey East Hampton East Hampton North 9.0/10 Wonderful (151) "We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. " CA $360 CA $453 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/77f9f5ea.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) ![Sports facility](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/abb4b75e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hero King Patio Deluxe | Terrace/patio](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/65048075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hero Beach Club Montauk 9.0/10 Wonderful (196) "Beach view and cozy vibes" CA $215 CA $382 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information) ![Beach bar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/52eefc00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/c930d525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/780134b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/65a8ebbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Sands Motel & Beach Bungalows Greenport 9.8/10 Exceptional (136) "Great hotel and location. " CA $363 CA $415 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/a4958436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/625fce42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/1ef9d54f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Madison Beach Hotel Madison Center 9.4/10 Exceptional (323) "the staff was exceptional and our dinner was very good" CA $425 CA $489 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/aa9cc8cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Suite](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/9bf97ebb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Cottage](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/6d8b086b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Cottage](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/5c9db42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Canoe Place Inn and Cottages Hampton Bays 9.8/10 Exceptional (58) "Amazing property. Really enjoyed our stay." CA $582 CA $705 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Inn-And-Cottages.h83519458.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/d84c46bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/e9d81899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/3f4839f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Topping Rose House Bridgehampton 9.2/10 Wonderful (135) "Great rooms, staff and food" CA $1,075 CA $1,234 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/fb2335a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, 1 Bedroom, Non Smoking (Room 322)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/94ca860b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, 1 Bedroom, Non Smoking (Room 211)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/89c2227e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/475ef317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copper Beech Inn Ivoryton 8.6/10 Excellent (504) "Had a fantastic room 324 in the newer building.. Breakfast was delicious and service terrific.." CA $392 CA $451 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information) ![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/b8adcc4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/1f4433ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/65a49724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/06408853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Roundtree, Amagansett Amagansett North 9.8/10 Exceptional (88) "The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. " CA $975 CA $1,170 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/67db121e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, American cuisine](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/d3bf1318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 4, King Bed](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/bf954008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/3e8af6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The 1770 House Restaurant & Inn East Hampton 9.8/10 Exceptional (157) "The staff was incredibly genuine and the property felt intimate and comfortable." CA $456 CA $624 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/East-Hampton-Hotels-The-1770-House-Restaurant-Inn.h1085655.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/99260f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Georgia Pond Junior Suite](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/e9e14566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/968c61db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Georgia Pond Junior Suite](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/386602b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Maidstone East Hampton 8.0/10 Very good (150) "We had a wonderful stay " CA $854 CA $976 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.Hotel-Information) ![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) ![Garden](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/98031383.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/e61ec435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/f09f38b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### James Pharmacy Bed & Breakfast Old Saybrook Center 9.2/10 Wonderful (19) "My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!" CA $424 CA $471 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/4db6535f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Master Guest Room](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/90421aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/d9c11af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/9d3a1088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Hampton Art House Bed & Breakfast Clearwater Beach 9.6/10 Exceptional (64) "Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. " CA $533 CA $609 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/East-Hampton-Hotels-East-Hampton-Art-House-Bed-Breakfast.h31007589.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/5689ac07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/253d38d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/934c8d81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/574b952f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Canoe Place Waterfront Residences Hampton Bays 10/10 Exceptional (1) [](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Waterfront-Residences.h109662697.Hotel-Information) ![One Bedroom Condo King with Steam Shower | Living area](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/fa3ad3aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Condo King with Steam Shower](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/80b0c655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Condo King with Steam Shower | Living area](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/a9bb02b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/439e74da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Offshore Residences Downtown Montauk CA $743 CA $1,009 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Montauk-Hotels-Offshore-Residences.h118940366.Hotel-Information) ![](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%2F4Star-Shelter-Island-Hotels.s40-0-d157359.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Shelter-Island-Hotels.s40-0-d157359.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Shelter Island. ![Mill House Inn](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Mill House Inn 31 North Main Street, East Hampton, NY CA $456 CA $573 total Oct 27 - Oct 28 includes taxes & fees 9/10 Wonderful! (70 reviews) [](https://expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) ![Casa Newmark Holiday home 7 BestStayz.1](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/23f4590c_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Casa Newmark Holiday home 7 BestStayz.1 112 Northwest Path, Sagaponack, NY [Get rates](https://expedia.ca/Hotel-Search?startDate=29%2F10%2F2025&endDate=30%2F10%2F2025&selected=32411044&PinnedHotelID=32411044&HadPinnedHotel=true®ionId=157359) [](https://expedia.ca/Sagaponack-Hotels-Casa-Newmark-Holiday-Home-7-BestStayz1.h32411044.Hotel-Information) Still don't see what you're looking for? [See all properties in Shelter Island.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=16%2F10%2F2025&endDate=17%2F10%2F2025®ionId=157359&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=16%2F10%2F2025&endDate=17%2F10%2F2025®ionId=157359&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=16%2F10%2F2025&endDate=17%2F10%2F2025®ionId=157359&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=16%2F10%2F2025&endDate=17%2F10%2F2025®ionId=157359&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=16%2F10%2F2025&endDate=17%2F10%2F2025®ionId=157359&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=16%2F10%2F2025&endDate=17%2F10%2F2025®ionId=157359&star=40&star=40&amenities=WATER_PARK) 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. ## Learn more about Shelter Island Escape to Shelter Island! Enjoy its island views, natural setting, and beaches. [See all hotels in Shelter Island](https://www.expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30&adults=2®ionId=157359) ![](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg?impolicy=fcrop&w=400&h=400&p=1&q=high) Photo by tom owens ## Top Shelter Island Hotel Reviews ![Marram](//images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0_y.jpg) ### Marram 10/10 Excellent "Ocean ciew" [](https://expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information) ![Montauk Yacht Club](//images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f_y.jpg) ### Montauk Yacht Club 10/10 Excellent "Staffs were so kind. The place was peaceful and it is really a relaxing place to stay especially it is beach front" [](https://expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Nice views on sunset" [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Gurney's Montauk Resort & Seawater Spa](//images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg) ### Gurney's Montauk Resort & Seawater Spa 10/10 Excellent "wonderful place only criticism is how far away rooms are from lobby and the rest of the facilities" [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ## Find out more about Shelter Island If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Shelter Island are calling your name. Known for providing first-rate service in amazing locations, each of the Shelter Island 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Shelter Island. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Shelter Island, New York, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Shelter Island hotels with 4 Stars provide everything you need to unwind in style. ## Frequently asked questions ### What are the best 4-star hotels in Shelter Island? > [The Pridwin Hotel](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information) is a 4-star hotel in Shelter Island that ranks highly among Expedia customers. A terrace and concierge services are some of its many amenities. Travellers also love staying at [Silver Sands Motel & Beach Bungalows](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information). From a terrace to dining romance packages, it features conveniences that cater to all aspects of your relaxation and entertainment. ### How much does it cost to stay in a 4-star hotel in Shelter Island? > Expedia can help you quickly track down the ideal 4-star hotel for your vacation in Shelter Island. Use our handy filter tool to tailor your search by things like price, amenities and star rating and get access to terrific deals in a few clicks. > > > > - Search for the lowest price from CA $573 ### What's the difference between 5-star and 4-star hotels in Shelter Island? > Treat yourself to refined living during your Shelter Island escape by staying at a 4-star hotel. As well as featuring upmarket accommodations, these retreats are typically packed with amenities such as complimentary bathrobes, large beds and more. A 5-star hotel will go the extra mile to make your trip an even more indulgent and unforgettable one. Round-the-clock concierge assistance, elegant furnishings and gourmet dining are a few of the superior conveniences and services you'll likely get access to. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [1 Star Hotels in Hamptons](https://www.expedia.ca/1Star-Hamptons-Hotels.s10-0-d6056452.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Plandome Heights](https://www.expedia.ca/1Star-Plandome-Heights-Hotels.s10-0-d553248634998735582.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Lindenhurst](https://www.expedia.ca/2Star-Lindenhurst-Hotels.s20-0-d183693.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Manorhaven](https://www.expedia.ca/2Star-Manorhaven-Hotels.s20-0-d553248634998695724.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Wheatley Heights](https://www.expedia.ca/2Star-Wheatley-Heights-Hotels.s20-0-d3000450118.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Flanders](https://www.expedia.ca/3Star-Flanders-Hotels.s30-0-d3000475689.Travel-Guide-Filter-Hotels) - 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[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 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) - [Visit Bay Point](https://www.expedia.ca/Sag-Harbor-Bay-Point.dx553248635976471151) - [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) - [Things to do in Greenport](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.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 4 Star Hotels in Shelter Island on Expedia.com](https://www.expedia.com/4Star-Shelter-Island-Hotels.s40-0-d157359.Travel-Guide-Filter-Hotels)