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 ![](https://images.trvl-media.com/place/157359/8df1734b-1204-4cc5-a5a0-67f90d8a76a3.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 availability on Shelter Island Heights Historic Hotels Tonight [Jan 23 - Jan 24](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-23&endDate=2026-01-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 24 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-24&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shelter Island Heights historic hotels ![Property entrance](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/d7688cb9.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) ![Garden](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/3b892c7c.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) ### The Maidstone [](https://www.expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.Hotel-Information) East Hampton 8.0/10 Very good (150 reviews) "We had a wonderful stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sabrina CA $240 CA $275 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.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) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943221/de85c2ae.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) ![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) ### 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 reviews) "Perfect Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dean J. CA $178 CA $293 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-NY-King-Suite-1.h71943221.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) ![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) ![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) ### American Beech - King Suite 2 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-King-Suite.h71943229.Hotel-Information) Greenport 10/10 Exceptional (2 reviews) "Excellent one night stay." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Patrick M. CA $178 CA $293 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-King-Suite.h71943229.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) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/9e0f05a8.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) ![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) ### 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 reviews) "We thoroughly enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Parent From The Heart, Inc. E. CA $164 CA $276 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.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) ![](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943243/278b9fb1.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) ![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) ### 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 reviews) "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 $205 CA $328 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Deluxe-King-5.h71943243.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/72000000/71950000/71943300/71943263/6988f7cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943263/12b2c14a.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 reviews) "Right in the heart of Greenport Villiage " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne B. CA $247 CA $384 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Deluxe-King-Suite-14.h71943263.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943261/96479bda.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/72000000/71950000/71943300/71943261/c3623721.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943261/9e0bed4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943261/ff5a9b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - Deluxe King Suite 12 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Deluxe-King-Suite-12.h71943261.Hotel-Information) Greenport CA $205 CA $328 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Deluxe-King-Suite-12.h71943261.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943257/61ac3b90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943257/bcabd706.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/72000000/71950000/71943300/71943257/366de111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943257/3f679fae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - Deluxe King Suite 11 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Two-Bedroom-Apartment-10.h71943257.Hotel-Information) Greenport CA $205 CA $328 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Two-Bedroom-Apartment-10.h71943257.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/44648b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, beach towels](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/b305c77f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/ebb70869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/7ee4af6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets! [](https://www.expedia.ca/Southampton-Hotels-Entire-House-In-Southampton-Village.h32202785.Hotel-Information) Southampton 9.0/10 Wonderful (10 reviews) "Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Panagiota K. CA $545 CA $1,233 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Southampton-Hotels-Entire-House-In-Southampton-Village.h32202785.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943253/3f78fdb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943253/4f3be2fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943253/bfa72810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943253/ec0d1670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - Two-Bedroom Apartment 8 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Two-Bedroom-Apartment-8.h71943253.Hotel-Information) Greenport CA $371 CA $545 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Two-Bedroom-Apartment-8.h71943253.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=2026-02-06&endDate=2026-02-07®ionId=183716&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Shelter Island Heights Hotel Reviews ![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 "From the front desk to the rest of the staff, everyone was very friendly but also very professional and very helpful. I called the front desk about 5 straight times to ask questions I was waiting for the receptionist to e upset ,to my surprise she was laughing it up with me. That alone made my stay great" [](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 "All was good at the hotel. No complaints" [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.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 "Nice place to stay" [](https://expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.Hotel-Information) ![Motel 6 Niantic, CT - New London](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039681/0c062ad1_y.jpg) ### Motel 6 Niantic, CT - New London 10/10 Excellent "The water was so hot I had the best shower in the morning!! I love hot showers and this was perfect the room was clean and it is right off the exit so in the morning I was right there by 95 abd the staff was very friendly both at check in and check out !! " [](https://expedia.ca/Niantic-Hotels-Motel-6-Niantic.h1039681.Hotel-Information) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "Great room and staff" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Staff was very friendly room was clean and comfortable " [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.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 "This hotel is clean and safe. Parking was easy. Rooms are spacious. Staff was friendly. It's not overly fancy but was perfect for a reasonable price. " [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.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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