Title: Book the Best HISTORIC Hotels in The Heights in 2025 | Expedia.ca [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)[The Heights Car Rentals](https://expedia.ca/Car-Rentals-In-The-Heights.d553248635976473534.Car-Rental-Guide)[The Heights Vacations](https://expedia.ca/The-Heights.d553248635976473534.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/4941e2fd68ce17b39e6de73e44df4c4b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Erisa Dilo # Find Historic Hotels in The Heights, NY from CA $426 ![](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 The Heights Historic Hotels Tonight [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=553248635976473534&startDate=2025-10-19&endDate=2025-10-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976473534&startDate=2025-10-20&endDate=2025-10-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976473534&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976473534&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top The Heights Historic Hotels ![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) ![Reception](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/d269b9f6.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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aniya CA $442 CA $604 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/East-Hampton-Hotels-The-1770-House-Restaurant-Inn.h1085655.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/433807ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/a3e46cd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/825be1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/e52f4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Driftwood Cottage @ Saybrook Point Marina, 2 King Beds Old Saybrook Center 9.6/10 Exceptional (38) "Great property, would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) charles b. CA $345 CA $718 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.Hotel-Information) ![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) ![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) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943221/2c441a78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943221/81d5d1e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport NY - King Suite 1 Greenport 10/10 Exceptional (5) "Perfect Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dean J. CA $293 CA $447 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-NY-King-Suite-1.h71943221.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/98e9a1b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/e5f6999f.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) ![Exterior detail](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/553f589d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Huntting Inn East Hampton 9.0/10 Wonderful (103) "What a wonderful place to stay! The room was beautiful. The bed was comfortable and the staff were welcoming and helpful. We loved how close it was to town. We also enjoyed the breakfast every morning. The Palm restaurant downstairs was nice to have on property and the food was great. We will definitely stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dena CA $536 CA $627 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/East-Hampton-Hotels-The-Huntting-Inn.h35373712.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943235/45ac1e17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943235/b28d56c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943235/4e11579b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943235/5b114246.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - King Suite 3 Greenport CA $293 CA $447 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-King-Suite-3.h71943235.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/72000000/71950000/71943300/71943243/265999f2.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/f35fc40e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943243/eca57b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech - Deluxe King 5 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 $321 CA $484 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Deluxe-King-5.h71943243.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/72000000/71950000/71943300/71943229/9a85fd03.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) ### American Beech - King Suite 2 Greenport 10/10 Exceptional (2) "Excellent one night stay." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Patrick M. CA $293 CA $447 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-King-Suite.h71943229.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943263/e5619a10.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) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943263/b6f6f364.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) ### American Beech - Deluxe King Suite 14 Greenport 10/10 Exceptional (2) CA $447 CA $646 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Deluxe-King-Suite-14.h71943263.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/27aa2ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, in-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/354f7655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Room, 1 King Bed](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/07ed4b21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/802040b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harpoon House Southampton 8.4/10 Very good (144) "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 CA $437 CA $500 total includes taxes & fees Nov 19 - Nov 20 [](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) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/9e0f05a8.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/e500d985.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) ### American Beech in Greenport - Petite King Room 7 Greenport 9.0/10 Wonderful (4) "Great job " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) emilio CA $279 CA $426 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.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=2025-11-02&endDate=2025-11-03®ionId=553248635976473534&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top The Heights Hotel Reviews ![Madison Beach Hotel](//images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg) ### Madison Beach Hotel 10/10 Excellent "Great ocean view " [](https://expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![Water's Edge Resort & Spa](//images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "We love the stay everything was perfect" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Great stay overall. Only suggestion would be to put a light on the side of the building. " [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Saybrook Point Resort & Marina](//images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "Beautiful property, we loved our room, friendly staff. " [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](//images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 10/10 Excellent "Our stay was just what we needed. Breakfast was full of choices and and plenty to eat and drink. A perfect stop in a lovely town." [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "Staff was incredibly communicative, kind, and patient. Definitely recommend and we would stay again!" [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ## Frequently asked questions ### What can a history buff expect from a stay in The Heights? > The historical places in The Heights are probably at the top of your sightseeing list. And don't forget to discover the other places of interest while you're in the area. ### How many historical hotels will I find in The Heights? > In The Heights, you'll find 13 hotels and other lodging options bookable on Expedia but not many designated as historic hotels. ### What are the top historical sites and other places in The Heights? > A couple of favorite places to visit are Sunset Beach and Shelter Island Country Club. You'll also find Crescent Beach and Railroad Museum of Long Island in the area. ### What is a historic hotel like in The Heights? > By choosing a historic hotel, you can spend a night or two in a place that has an official historic designation. A castle, a palace or even a pub or an old police station can be turned into a historic hotel as long as it's of special interest. Traditional architecture and period features are typically preserved within the guestrooms or public spaces of historic hotels in The Heights, giving a historical feel. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is a term often used in Asia and Europe, while "historic hotel" is a term often used in the U.S. but overall the terms are quite similar. The architecture and actual building of a historic hotel tends to be what's most significant. For a heritage hotel, it's often the cultural value and how it shaped the community. ### Do historic hotels in The Heights have modern facilities? > Hotel interiors feature the modern conveniences and safety features you've come to expect, while every effort is made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities, and the amenities found in a hotel will be available in a historic hotel. Rest assured that when you select a historic hotel in The Heights, you won't find a place that is rundown or uncomfortable. ## 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) - [Hotels with Waterslides in Brooklyn](https://www.expedia.ca/Brooklyn-Hotels-Hotels-With-Waterslides.0-0-d177851-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Ski Hotels in Brooklyn](https://www.expedia.ca/Brooklyn-Hotels-Ski-Hotel.0-0-d177851-tSkiHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Brooklyn](https://www.expedia.ca/Brooklyn-Hotels-Waterpark-Hotels.0-0-d177851-tWaterparkHotels.Travel-Guide-Filter-Hotels) - 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