Title: Book the Best HISTORIC Hotels in Smithtown in 2026 | Expedia.ca [Hotels in Smithtown](https://expedia.ca/Smithtown-Hotels.d6921.Travel-Guide-Hotels)[Vacation Rentals in Smithtown](https://expedia.ca/Smithtown-Vacation-Rentals.d6921.Travel-Guide-VacationRentals)[Smithtown Car Rentals](https://expedia.ca/Car-Rentals-In-Smithtown.d6921.Car-Rental-Guide)[Smithtown Vacation Packages](https://expedia.ca/Smithtown.d6921.Destination-Travel-Guides) ![Spring warmth at the Greenbelt Trail along the Kings Park Bluffs and Sunken Meadow Park on the North Shore of Long Island. A bare tree near clear water, it looks reminiscent of the Caribbean Sea.](https://images.trvl-media.com/place/6921/0b6298ca-06c0-4b95-baa8-85105480c051.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Smithtown, NY from CA $279 - ![](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 Smithtown Historic Hotels Tonight [Dec 6 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6921&startDate=2025-12-06&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 7 - Dec 8](https://www.expedia.ca/Hotel-Search?regionId=6921&startDate=2025-12-07&endDate=2025-12-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6921&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6921&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Smithtown Historic Hotels ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/40000/35600/35577/ea5f5685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/40000/35600/35577/9d4935b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Waterview](https://images.trvl-media.com/lodging/1000000/40000/35600/35577/96f22ea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/1000000/40000/35600/35577/0f0de723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Danfords Hotel and Marina Port Jefferson 8.4/10 Very good (1003) "Excellent, pleasant front desk service" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $204 CA $279 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Port-Jefferson-Hotels-Danfords-Hotel-And-Marina.h35577.Hotel-Information) ![Standard Room, 1 King Bed, Main Building | Property entrance](https://images.trvl-media.com/lodging/7000000/6510000/6502000/6501905/552e9d83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, Kitchen | Private kitchen](https://images.trvl-media.com/lodging/7000000/6510000/6502000/6501905/45533217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/7000000/6510000/6502000/6501905/f5b2690f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/7000000/6510000/6502000/6501905/cf0be66e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Guesthouse at Norwalk Inn Norwalk 8.4/10 Very good (40) "it was amazing will stay again food was good comfort was great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) anthony CA $366 CA $421 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Stamford-Hotels-Guesthouse-At-Norwalk-Inn.h6501905.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1040000/1037700/1037678/c5b41b0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1040000/1037700/1037678/f75d93d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/2000000/1040000/1037700/1037678/9cc27509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1040000/1037700/1037678/44e4f674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oheka Castle Hotel & Estate Huntington 9.0/10 Wonderful (646) "Charming location, huge rooms. Restaurant only okay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole CA $583 CA $666 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Huntington-Hotels-Oheka-Castle-Hotel-Estate.h1037678.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34150000/34141500/34141417/352e57b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34150000/34141500/34141417/0eba97fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34150000/34141500/34141417/4015e43f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34150000/34141500/34141417/3c70b970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4 BR. 2 BTH, HOT TUB, MINS TO JONES BEACH, MINS TO RIVIERA WALK TO TRAIN TO NYC Massapequa 10/10 Exceptional (12) "Just a comfortable, pleasant experience for four generations of family, ages 1 month to 80 Room to spread out, house functions so well. Lots of amenities Restaurants nearby" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Madeleine T. CA $2,073 CA $3,874 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Massapequa-Hotels-4-BR-2-BTH.h34141417.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=2025-12-20&endDate=2025-12-21®ionId=6921&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Smithtown Hotel Reviews ![Viana Hotel and Spa, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/4000000/3060000/3056400/3056354/cadbaf1c_y.jpg) ### Viana Hotel and Spa, Trademark Collection by Wyndham 10/10 Excellent "The place and the staff are all wonderful!" [](https://expedia.ca/Westbury-Hotels-Viana-Hotel-And-Spa.h3056354.Hotel-Information) ![Norwalk Inn & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/15200/15114/13ab5174_y.jpg) ### Norwalk Inn & Conference Center 10/10 Excellent "My experience at the Norwalk Inn & Conference Center was beautiful from start to finish. The staff made me feel at home with their warmth and professionalism. The room was spotless and cozy, and the hotel’s atmosphere felt calm and inviting. I’m grateful for such a pleasant and memorable stay. Thanks" [](https://expedia.ca/Stamford-Hotels-Norwalk-Inn.h15114.Hotel-Information) ![ Holiday Inn Express Hauppauge-Long Island](https://images.trvl-media.com/lodging/1000000/690000/687900/687847/b9a8a7cb_y.jpg) ### Holiday Inn Express Hauppauge-Long Island 10/10 Excellent "It was my first time there with my Girlfriend and we both loved the hotel because it was the first hotel we went to together. I’m glad that I chose the holiday inn express as the first hotel to go with my girlfriend to, the room was very clean, staff was very nice to us upon the walk in, and the breakfast was very good to us. I’m planning on coming back this Friday for a full weekend stay with my girl this time and I hope we will be welcome the same way we were when we first came there. I’m very excited to have a full weekend stay and see what the hotel is all about instead of staying barely a full day " [](https://expedia.ca/Hauppauge-Hotels-Holiday-Inn-Express-Hauppauge.h687847.Hotel-Information) ![Hilton Garden Inn Westbury](https://images.trvl-media.com/lodging/1000000/990000/988800/988765/a35583f8_y.jpg) ### Hilton Garden Inn Westbury 10/10 Excellent "Clean, basic. Perfect for what we needed " [](https://expedia.ca/Westbury-Hotels-Hilton-Garden-Inn-Westbury.h988765.Hotel-Information) ![Radisson Hotel Hauppauge-Long Island](https://images.trvl-media.com/lodging/1000000/20000/10800/10706/db515945_y.jpg) ### Radisson Hotel Hauppauge-Long Island 10/10 Excellent "Amazing Will stay again" [](https://expedia.ca/Hauppauge-Hotels-Radisson-Hotel-Hauppauge-Long-Island.h10706.Hotel-Information) ![Hyatt Regency Long Island](https://images.trvl-media.com/lodging/1000000/10000/3700/3668/79d8acea_y.jpg) ### Hyatt Regency Long Island 10/10 Excellent "Our stay was very pleasant! My only negatives…some of the staff at the front desk could be more pleasant and engaging…eye contact rather than focus on a computer screen. In addition, the elevators are very slow." [](https://expedia.ca/Hauppauge-Hotels-Hyatt-Regency-Long-Island.h3668.Hotel-Information) ![Days Inn by Wyndham Woodbury Long Island](https://images.trvl-media.com/lodging/1000000/10000/6700/6675/2e6a9e91_y.jpg) ### Days Inn by Wyndham Woodbury Long Island 10/10 Excellent "Very friendly staff. Clean room. Good coffee. No breakfast " [](https://expedia.ca/Woodbury-Hotels-Days-Inn-By-Wyndham-Woodbury-Long-Island.h6675.Hotel-Information) ![East Norwich Inn](https://images.trvl-media.com/lodging/1000000/10000/2100/2024/fa5b4526_y.jpg) ### East Norwich Inn 10/10 Excellent "All good. As usual. " [](https://expedia.ca/East-Norwich-Hotels-East-Norwich-Inn-Oyster-Bay.h2024.Hotel-Information) ![Holiday Inn Plainview-Long Island by IHG](https://images.trvl-media.com/lodging/1000000/10000/8700/8686/691a6724_y.jpg) ### Holiday Inn Plainview-Long Island by IHG 10/10 Excellent "Very clean, all staff friendly and attentive. Restaurant was very good. And the coffee in the lobby was AMAZING! We were so happy with our stay. " [](https://expedia.ca/Plainview-Hotels-Holiday-Inn-Plainview.h8686.Hotel-Information) ## Frequently asked questions ### What can a history enthusiast expect from a trip to Smithtown? ### How many historical hotels are located in Smithtown? ### What are the top historical places and other sights to visit in Smithtown? ### What is a historic hotel like in Smithtown? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Smithtown have modern facilities? ## Explore a world of travel with Expedia - Lodging - 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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