Title: Book the Best HISTORIC Hotels in Shelter Island Heights in 2026 | Expedia.ca [Hotels in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Vacation-Rentals.d183716.Travel-Guide-VacationRentals)[Things to do in Shelter Island Heights](https://expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)[Shelter Island Heights Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island-Heights.d183716.Car-Rental-Guide)[Shelter Island Heights Vacation Packages](https://expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides) ![View of Dering Harbor](https://images.trvl-media.com/place/157359/8df1734b-1204-4cc5-a5a0-67f90d8a76a3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Brian V. Rowe # Find Historic Hotels in Shelter Island Heights, NY from CA $360 - ![](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 Heights Historic Hotels Tonight [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-12-22&endDate=2025-12-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 23 - Dec 24](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-12-23&endDate=2025-12-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shelter Island Heights historic hotels ![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) ![Reception](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/d269b9f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/67db121e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Carriage House | Living area](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/6a224301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The 1770 House Restaurant & Inn [](https://www.expedia.ca/East-Hampton-Hotels-The-1770-House-Restaurant-Inn.h1085655.Hotel-Information) East Hampton 9.8/10 Exceptional (161) "The staff was incredibly genuine and the property felt intimate and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aniya CA $381 CA $521 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/East-Hampton-Hotels-The-1770-House-Restaurant-Inn.h1085655.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/a44e62eb.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) ### Hero Beach Club [](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information) Montauk 9.0/10 Wonderful (202) "Great weekend trip " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy CA $223 CA $395 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943221/f03e38bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943221/6c2db181.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943221/2c441a78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943221/de85c2ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport NY - King Suite 1 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-NY-King-Suite-1.h71943221.Hotel-Information) Greenport 10/10 Exceptional (5) "Perfect Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dean J. CA $247 CA $382 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-NY-King-Suite-1.h71943221.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/d7688cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Queen](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/6ddcc118.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/3b892c7c.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 [](https://www.expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.Hotel-Information) East Hampton 8.0/10 Very good (150) "We had a wonderful stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sabrina CA $315 CA $360 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943229/78e2058f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943229/6f63cb0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943229/e21d51ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943229/52c91315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech - King Suite 2 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-King-Suite.h71943229.Hotel-Information) Greenport 10/10 Exceptional (2) "Excellent one night stay." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Patrick M. CA $247 CA $382 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-King-Suite.h71943229.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/2ac0e6c9.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) ### Harpoon House [](https://www.expedia.ca/Southampton-Hotels-Harpoon-House.h36879849.Hotel-Information) Southampton 8.4/10 Very good (148) "Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karissa [](https://www.expedia.ca/Southampton-Hotels-Harpoon-House.h36879849.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0195b6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/ca1c5177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/18f698b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0884fbbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - Petite King Room 7 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) Greenport 9.0/10 Wonderful (4) "We thoroughly enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Parent From The Heart, Inc. E. CA $247 CA $383 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943263/63a26399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943263/dfe21282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943263/b6f6f364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943263/6988f7cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech - Deluxe King Suite 14 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Deluxe-King-Suite-14.h71943263.Hotel-Information) Greenport 10/10 Exceptional (2) "Right in the heart of Greenport Villiage " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne B. CA $316 CA $476 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Deluxe-King-Suite-14.h71943263.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943243/3e210a29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943243/da3cce8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943243/265999f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943243/278b9fb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech - Deluxe King 5 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Deluxe-King-5.h71943243.Hotel-Information) Greenport 8.6/10 Excellent (4) "I thoroughly enjoyed my stay. I was upgraded before arriving at the hotel and was very pleased with my stay. The staff were kind and accommodating, I will definitely return." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ayana M. CA $275 CA $421 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Deluxe-King-5.h71943243.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/e5f6999f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/98e9a1b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/2a96c58c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free continental breakfast on weekends](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/062f5fd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Huntting Inn [](https://www.expedia.ca/East-Hampton-Hotels-The-Huntting-Inn.h35373712.Hotel-Information) Egypt Lane Historic District 9.0/10 Wonderful (104) "Staff and management was very welcoming!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sanailer CA $528 CA $617 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/East-Hampton-Hotels-The-Huntting-Inn.h35373712.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=2026-01-05&endDate=2026-01-06®ionId=183716&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Shelter Island Heights Hotel Reviews ![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 "Everything was wonderful. Staff was friendly, very clean,we enjoyed it." [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.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 "Room was clean though a bit rustic. Staff was very nice. No housekeeping but was able to collect all clean towels, etc. in the office. We were here for a funeral. Pier Blue Inn was close to funeral home, Catholic Church, and repast. Nice restaurants so close by! I’m glad I booked this place. Added a second night to avoid Friday night traffic back to our house in Rockland County NY." [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Best Western Niantic - New London/Mystic Area](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/w3834h2560x6y0-25f93ce9_y.jpg) ### Best Western Niantic - New London/Mystic Area 10/10 Excellent "everything was well remodeled and comfortable." [](https://expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.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 10/10 Excellent "The staff was friendly. The room was good. " [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.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 "Friendly and helpful staff, wonderful dining experience at Fresh Salt" [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Sleep Inn & Suites Niantic North](https://images.trvl-media.com/lodging/1000000/860000/851700/851700/cf19af3a_y.jpg) ### Sleep Inn & Suites Niantic North 10/10 Excellent "Very clean room Did not have the breakfast as we left prior to it starting. Would stay there again " [](https://expedia.ca/Niantic-Hotels-Sleep-Inn-Suites-Niantic.h851700.Hotel-Information) ![Beachcomber Resort at Montauk](https://images.trvl-media.com/lodging/3000000/2220000/2212000/2211971/d4cb08d2_y.jpg) ### Beachcomber Resort at Montauk 10/10 Excellent "Beautiful views and so close to town. Walk right down the driveway to the ocean! " [](https://expedia.ca/Montauk-Hotels-Beachcomber-At-Montauk.h2211971.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Shelter Island Heights? ### How many historical hotels will I find in Shelter Island Heights? ### What are the top historical sites and other places to visit in Shelter Island Heights? ### What is a historic hotel like in Shelter Island Heights? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Shelter Island Heights have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Beach Hotel Hotels in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Beach-Hotel.0-0-d177851-tBeachHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Business-Hotel.0-0-d177851-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Brooklyn ](https://www.expedia.ca/Brooklyn-Hotels-Honeymoon-Hotels.0-0-d177851-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - 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