Title: 4 Stars Hotels in Dering Harbor, Shelter Island from CA $416 - Find Cheap Dering Harbor Hotels With 4 Stars | Expedia.ca [Dering Harbor Travel Guide](https://expedia.ca/Dering-Harbor.dx553248634998885605)[Hotels in Dering Harbor](https://expedia.ca/Dering-Harbor-Hotels.d553248634998885605.Travel-Guide-Hotels)[Vacation Rentals in Dering Harbor](https://expedia.ca/Dering-Harbor-Vacation-Rentals.d553248634998885605.Travel-Guide-VacationRentals)[Flights to Dering Harbor](https://expedia.ca/Cheap-Flights-To-Dering-Harbor.d553248634998885605.Travel-Guide-Flights)[Things to do in Dering Harbor](https://expedia.ca/Things-To-Do-In-Dering-Harbor.d553248634998885605.Travel-Guide-Activities)[Dering Harbor Car Rentals](https://expedia.ca/Car-Rentals-In-Dering-Harbor.d553248634998885605.Car-Rental-Guide)[Dering Harbor Vacation Packages](https://expedia.ca/Dering-Harbor.d553248634998885605.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 4 Stars Hotels in Dering Harbor, Shelter Island from CA $416 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Dering Harbor 4 Star Hotels Tonight [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2025-10-04&endDate=2025-10-05&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2025-10-05&endDate=2025-10-06&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Dering Harbor 4 Star Hotels ![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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/4c9856c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sound View Greenport Greenport 8.4/10 Very good (575) "Loved everything about my stay at the Sound view !! " CA $346 CA $464 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/560aa55e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/72a59251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/575a076f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Balcony (The Barons Suite - Water View)](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/c87b4212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baron's Cove 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 (79) "Shelter Island is definitely a gem" CA $388 CA $488 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) ![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) ![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) ![Lobby sitting area](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/d697dbfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Journey East Hampton East Hampton North 9.0/10 Wonderful (149) "We had a good stay at The Journey. Can’t wait to come back! " CA $396 CA $497 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.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) ![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) ![Waterfront Beach Shack Studio | View from room](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/8f5285b2.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) ### Silver Sands Motel & Beach Bungalows Greenport 9.8/10 Exceptional (132) "Beautiful beach all was great, loved breakfast At on site diner Nookies!" CA $364 CA $416 total includes taxes & fees Oct 6 - Oct 7 [](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) ![Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/b8f87b0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Madison Beach Hotel Madison Center 9.4/10 Exceptional (320) "the staff was exceptional and our dinner was very good" CA $427 CA $491 total includes taxes & fees Nov 4 - Nov 5 [](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) ![Standard Cottage](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/5c9db42d.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) ### Canoe Place Inn and Cottages Hampton Bays 9.8/10 Exceptional (58) "Amazing property. Really enjoyed our stay." CA $573 CA $695 total includes taxes & fees Oct 15 - Oct 16 [](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) ![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/e9d81899.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) ![Cottage, 2 Single Beds | View from room](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/9125969a.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 $717 CA $825 total includes taxes & fees Oct 20 - Oct 21 [](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) ![Staircase](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/475ef317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/a99c206a.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) ### 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 $389 CA $448 total includes taxes & fees Oct 9 - Oct 10 [](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) ![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/c6fa26de.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) ### 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 $829 CA $995 total includes taxes & fees Oct 7 - Oct 8 [](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) ![Reception](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/d269b9f6.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) ### 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 $453 CA $620 total includes taxes & fees Oct 6 - Oct 7 [](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) ![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) ![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) ### The Maidstone East Hampton 8.0/10 Very good (148) "We had a wonderful stay " CA $680 CA $777 total includes taxes & fees Oct 8 - Oct 9 [](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/79000000/78200000/78191100/78191036/1891e70e.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 9.4/10 Exceptional (18) "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 $421 CA $468 total includes taxes & fees Oct 6 - Oct 7 [](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) ![Beach nearby](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/6809b461.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 $530 CA $605 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) ![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) ![Flat-screen TV](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/ef1a1d3d.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) ### Canoe Place Waterfront Residences Hampton Bays 10/10 Exceptional (1) [](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Waterfront-Residences.h109662697.Hotel-Information) ![Reception hall](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/59df497c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/f42806db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/b79b89fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/2c06a5e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 434 on Main Amagansett North 10/10 Exceptional (36) "Great hosts" [](https://www.expedia.ca/Amagansett-Hotels-434-On-Main.h12779331.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/2db832c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/100d4ecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/bc04c799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/123bbe23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day Peconic 9.6/10 Exceptional (138) "We had a wonderful stay at Andrew's house! The pool, hot tub, yard, and poolhouse are meticulously maintained. My 2 children (ages 2 and 4) loved their time in the pool, playing on the large lawn, and using the hammock. The house itself has a full kitchen and laundry with a large dining table great for a family. The location was beautiful--very close to wineries and lots of farmstands. We drove about 12 minutes to Greenport for an excellent dinner. Andrew was very friendly and helpful. ... [](https://www.expedia.ca/Peconic-Hotels-NORTHFORK-COTTAGE-With-POOL-HOTTUB.h35037604.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/754e4cf1_edited_1afd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, stereo](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/w3455h2297x0y1-853cf7f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/b51e6bb8_edited_d588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/248f6e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard Sag Harbor 10/10 Exceptional (11) "Our short trip to sag harbor was planned very last minute. Raymond was more the than happy to accommodate and left us a really nice goody bag to boot !! The house was newly renovated with all the expected amenities. Lots of sleeping quarters yet felt cozy. From the pool and pool house, the outdoor kitchen, “driving range” and gym there was something for everyone !! Raymond was a gracious host!" [](https://www.expedia.ca/Sag-Harbor-Hotels-5-Min-Walk-To-Beach-Restaurants-Museums-Village-House-With-Large-Backyard.h53890717.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/w860h368x0y0-6172fc5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/w1169h650x0y0-3f68a3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/w1170h1461x0y0-bc75bc71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/3e9b9c2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Rams Head Inn Shelter Island Heights 7.6/10 Good (18) "Beautiful views and lovely service " [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Rams-Head-Inn.h89981758.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/f2989301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/71becd12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/07d5462f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/7187781f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Farmhouse Bed and Breakfast Cutchogue 10/10 Exceptional (13) "very comfortable stay. " [](https://www.expedia.ca/Cutchogue-Hotels-The-Farmhouse-Bed-And-Breakfast.h90786314.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-Dering-Harbor-Hotels.s40-0-d553248634998885605.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Dering-Harbor-Hotels.s40-0-d553248634998885605.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 Dering Harbor. ![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 $384 CA $482 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=18%2F10%2F2025&endDate=19%2F10%2F2025&selected=32411044&PinnedHotelID=32411044&HadPinnedHotel=true®ionId=553248634998885605) [](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 Dering Harbor.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=05%2F10%2F2025&endDate=06%2F10%2F2025®ionId=553248634998885605&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=05%2F10%2F2025&endDate=06%2F10%2F2025®ionId=553248634998885605&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=05%2F10%2F2025&endDate=06%2F10%2F2025®ionId=553248634998885605&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=05%2F10%2F2025&endDate=06%2F10%2F2025®ionId=553248634998885605&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=05%2F10%2F2025&endDate=06%2F10%2F2025®ionId=553248634998885605&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=05%2F10%2F2025&endDate=06%2F10%2F2025®ionId=553248634998885605&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. ## Top Dering Harbor Hotel Reviews ![Baron's Cove](//images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/560aa55e_y.jpg) ### Baron's Cove 10/10 Excellent "Parking was free and really easy. Great proximity to the main street of town—you can easily walk, but it's not too close where it gets loud at night. The front staff and cleaning team were all lovely and super helpful. We loved the coffee bar in the mornings. " [](https://expedia.ca/Sag-Harbor-Hotels-Barons-Cove.h1148848.Hotel-Information) ![The Pridwin Hotel](//images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/fa5a1a49_y.jpg) ### The Pridwin Hotel 10/10 Excellent "The Pridwin is a beautiful property with a stunning view and old New England, Americana historic vibe. It is a quintessential experience if you want to have quiet yet convenience to both the north and south forks. The ferry is quick and the island is beautiful and quiet if you go during off season. Lovely long weekend trip for me and my husband. Highly recommend. " [](https://expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Clean and beautiful view" [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ## Find out more about Dering Harbor 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 Dering Harbor are calling your name. Known for providing first-rate service in amazing locations, each of the Dering Harbor 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 Dering Harbor. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Dering Harbor, Shelter Island, 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 Dering Harbor hotels with 4 Stars provide everything you need to unwind in style. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - 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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[Visit Shelter Island](https://www.expedia.ca/Shelter-Island.dx157359) - [Car rental Greenport](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide) - [Car rental Shelter Island](https://www.expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide) - [Shelter Island Vacation Rentals](https://www.expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals) - [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) - [Things to do in Shelter Island](https://www.expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities) - [Book 4 Star Hotels in Dering Harbor on Expedia.com](https://www.expedia.com/4Star-Dering-Harbor-Hotels.s40-0-d553248634998885605.Travel-Guide-Filter-Hotels)