Title: Book the Best HISTORIC Hotels in Chappaqua in 2025 | Expedia.ca [Hotels in Chappaqua](https://expedia.ca/Chappaqua-Hotels.d88470.Travel-Guide-Hotels)[Vacation Rentals in Chappaqua](https://expedia.ca/Chappaqua-Vacation-Rentals.d88470.Travel-Guide-VacationRentals)[Chappaqua Car Rentals](https://expedia.ca/Car-Rentals-In-Chappaqua.d88470.Car-Rental-Guide)[Chappaqua Vacation Packages](https://expedia.ca/Chappaqua.d88470.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) # Find Historic Hotels in Chappaqua, NY from CA $165 ![](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 Chappaqua Historic Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=88470&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=88470&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=88470&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=88470&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chappaqua Historic Hotels ![Restaurant](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Non Smoking (Stone Cottages at Bear Mountain)](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/42067525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/13890846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Overlook Lodge at Bear Mountain Bear Mountain 8.4/10 Very good (1012) "Clean room, easy parking" CA $145 CA $165 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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) ![Apartment, Kitchen](https://images.trvl-media.com/lodging/7000000/6510000/6502000/6501905/fe27070f.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) ### Guesthouse at Norwalk Inn Norwalk 8.4/10 Very good (39) "it was amazing will stay again food was good comfort was great " CA $363 CA $418 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Stamford-Hotels-Guesthouse-At-Norwalk-Inn.h6501905.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256205/3b78b19a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256205/0a60ddfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256205/0230a235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256205/d411dbe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food CROTON HDSN 9.8/10 Exceptional (90) "Maria is a wonderful host. We enjoyed our stay. Thank you." CA $143 CA $361 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/White-Plains-Hotels-Luxury-2bd-Comfortstyle-45min-To-Nyc.h33256205.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/67801e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/e56d490f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/dfec5e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands Fort Montgomery 9.8/10 Exceptional (122) "It has an incredible mountain and water view. " CA $263 CA $431 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) ![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/55000000/54540000/54535200/54535197/d983ed1f.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/55000000/54540000/54535200/54535197/c3199292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels](https://images.trvl-media.com/lodging/55000000/54540000/54535200/54535197/0d602375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels](https://images.trvl-media.com/lodging/55000000/54540000/54535200/54535197/7b23e036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The West Lane Inn - King Room Ridgefield 10/10 Exceptional (1) " the complimentary breakfast" CA $556 CA $636 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Danbury-Hotels-The-West-Lane-Inn-King-Room.h54535197.Hotel-Information) ![2 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/55000000/54540000/54535300/54535230/527413aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/55000000/54540000/54535300/54535230/2e228789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/55000000/54540000/54535300/54535230/4eadb8e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels](https://images.trvl-media.com/lodging/55000000/54540000/54535300/54535230/a59a6810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The West Lane Inn - Family Suite Ridgefield CA $1,103 CA $1,260 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Danbury-Hotels-The-West-Lane-Inn-Family-Suite.h54535230.Hotel-Information) ![Sport court](https://images.trvl-media.com/lodging/119000000/118060000/118052700/118052668/ac7e4d9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/119000000/118060000/118052700/118052668/63611c72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/119000000/118060000/118052700/118052668/59025e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/119000000/118060000/118052700/118052668/ae1bec2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2-bedroom condo in charming Wilton with AC, fitness room, WiFi Wilton CA $450 CA $943 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Wilton-Hotels-2-Bedroom-Condo-In-Charming-Wilton-With-AC.h118052668.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=2025-10-28&endDate=2025-10-29®ionId=88470&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chappaqua Hotel Reviews ![Clinton Inn Hotel & Event Center](//images.trvl-media.com/lodging/1000000/20000/16200/16115/aa583634_y.jpg) ### Clinton Inn Hotel & Event Center 10/10 Excellent "Was there for a wedding!!!" [](https://expedia.ca/Tenafly-Hotels-Clinton-Inn-Hotel-Event-Center.h16115.Hotel-Information) ![Sonesta White Plains Downtown](//images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg) ### Sonesta White Plains Downtown 10/10 Excellent "Staff very friendly easy check in and checkout " [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![Ardsley Acres Hotel Westchester](//images.trvl-media.com/lodging/2000000/1170000/1166900/1166864/4b305bf7_y.jpg) ### Ardsley Acres Hotel Westchester 10/10 Excellent "The heating is very weak. Must improve before freezing weather. Would be nice to have more than two sets of towels for two occupants" [](https://expedia.ca/White-Plains-Hotels-Ardsley-Acres-Hotel-Westchester.h1166864.Hotel-Information) ![Armoni Inn & Suites](//images.trvl-media.com/lodging/1000000/20000/12100/12036/5f0c23aa_y.jpg) ### Armoni Inn & Suites 10/10 Excellent "We're staying in the hotel for one night with our friends. We're going to say that it is long time we didn't see so good hotel for so low price. Recommended. " [](https://expedia.ca/Orangeburg-Hotels-Armoni-Inn-Suites.h12036.Hotel-Information) ![Royal Regency Hotel](//images.trvl-media.com/lodging/1000000/50000/40900/40814/c5903df6_y.jpg) ### Royal Regency Hotel 10/10 Excellent "Cleaned, staff excellent service " [](https://expedia.ca/White-Plains-Hotels-Royal-Regency-Hotel.h40814.Hotel-Information) ![Norwalk Inn & Conference Center](//images.trvl-media.com/lodging/1000000/20000/15200/15114/13ab5174_y.jpg) ### Norwalk Inn & Conference Center 10/10 Excellent "Nice room, nice staff, easy check in, plenty of parking, good location to all things Norwalk and Westport!" [](https://expedia.ca/Stamford-Hotels-Norwalk-Inn.h15114.Hotel-Information) ![Tarrytown House Estate](//images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg) ### Tarrytown House Estate 10/10 Excellent "Awesome staff and beautiful room" [](https://expedia.ca/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information) ![Ramada by Wyndham Bronx](//images.trvl-media.com/lodging/1000000/470000/462500/462463/c9951f9d_y.jpg) ### Ramada by Wyndham Bronx 10/10 Excellent "Good place" [](https://expedia.ca/New-York-Hotels-Ramada-By-Wyndham-Bronx.h462463.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Stamford / New York City](//images.trvl-media.com/lodging/1000000/30000/25000/24963/af81668d_y.jpg) ### La Quinta Inn & Suites by Wyndham Stamford / New York City 10/10 Excellent "Yes" [](https://expedia.ca/Stamford-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Stamford-New-York-City.h24963.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Chappaqua? > A trip to the historical sites in Chappaqua is probably at the top of your travel itinerary. Why not absorb the local color with a visit to the restaurants? ### How many historical hotels are there in Chappaqua? > Chappaqua is home to 6 hotels and other lodging options bookable on Expedia but not many designated as historic hotels. ### What are the most important historical sites and other places in Chappaqua? > A favorite place to visit is Hardscrabble Wilderness Area. You'll also find Travelers Rest and Thomas J. Watson Research Center in the area. ### What is a historic hotel like in Chappaqua? > By booking a historic hotel, guests can spend a night or two in a place that has an officially recognized historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be turned into a historic hotel as long as it has special significance. Traditional architecture and period features are often found in the communal spaces and guestrooms of these historic hotels in Chappaqua, giving a real sense of character. ### 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 historic hotels tend to be what's most significant. For a heritage hotel, it's mainly the cultural value and how it shaped the community. ### Do historic hotels in Chappaqua have modern facilities? > Hotels include modern conveniences and safety features you might expect, though efforts have been made to preserve the historic aspects and traditions. Private rooms with updated bathroom facilities, free WiFi, and the normal amenities found in most hotels will also be available in a historic hotel. When you book a historic hotel in Chappaqua, don't worry that you'll be staying at a place that's uncomfortable for guests or simply rundown. ## Explore a world of travel with Expedia - Lodging - More ways to book - [Beach Hotel Hotels in Armonk](https://www.expedia.ca/Armonk-Hotels-Beach-Hotel.0-0-d9324-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Armonk](https://www.expedia.ca/Armonk-Hotels-Cheap-Hotels.0-0-d9324-tCheapHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Armonk](https://www.expedia.ca/Armonk-Hotels-Golf-Hotel.0-0-d9324-tGolfHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Armonk](https://www.expedia.ca/Armonk-Hotels-Luxury-Hotel.0-0-d9324-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Armonk](https://www.expedia.ca/Armonk-Hotels-Pet-Friendly-Hotel.0-0-d9324-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Armonk](https://www.expedia.ca/Armonk-Hotels-Romantic-Hotel.0-0-d9324-tRomanticHotel.Travel-Guide-Filter-Hotels) - 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