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 $191 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=88470&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=88470&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=88470&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=88470&startDate=2025-10-10&endDate=2025-10-12&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 (1001) "Wonderful staff!" CA $168 CA $191 total includes taxes & fees Nov 3 - Nov 4 [](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) ![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) ![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) ### Guesthouse at Norwalk Inn Norwalk 8.4/10 Very good (39) "it was amazing will stay again food was good comfort was great " CA $331 CA $381 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Stamford-Hotels-Guesthouse-At-Norwalk-Inn.h6501905.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) ![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) ![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.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 $262 CA $423 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256205/d411dbe1.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) ### 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 $171 CA $396 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/White-Plains-Hotels-Luxury-2bd-Comfortstyle-45min-To-Nyc.h33256205.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/55000000/54540000/54535200/54535197/8e81d004.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) ![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) ### The West Lane Inn - King Room Ridgefield 10/10 Exceptional (1) " the complimentary breakfast" CA $553 CA $632 total includes taxes & fees Oct 7 - Oct 8 [](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) ![Hair dryer, towels](https://images.trvl-media.com/lodging/55000000/54540000/54535300/54535230/c31b1367.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) ### The West Lane Inn - Family Suite Ridgefield CA $1,098 CA $1,254 total includes taxes & fees Oct 22 - Oct 23 [](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) ![Miscellaneous](https://images.trvl-media.com/lodging/119000000/118060000/118052700/118052668/ae1bec2d.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) ![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) ### 2-bedroom condo in charming Wilton with AC, fitness room, WiFi Wilton CA $429 CA $915 total includes taxes & fees Nov 3 - Nov 4 [](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=2025-10-17&endDate=2025-10-18®ionId=88470&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chappaqua Hotel Reviews ![Amsterdam Hotel](//images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg) ### Amsterdam Hotel 10/10 Excellent "Friendly. Accommodating. Ample parking. Quiet rooms. Some fixtures and surfaces are dated, but I knew this coming in. Great hotel for the price. " [](https://expedia.ca/Stamford-Hotels-Amsterdam-Hotel.h20793.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 "They did a great job of renovating the property. By keep the night stay a little higher keeps the riff-raff out. Great place!! " [](https://expedia.ca/White-Plains-Hotels-Ardsley-Acres-Hotel-Westchester.h1166864.Hotel-Information) ![Baymont by Wyndham White Plains - Elmsford](//images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34_y.jpg) ### Baymont by Wyndham White Plains - Elmsford 10/10 Excellent "Everything was great, would have preferred a vent in the bathroom, otherwise I’m glad we stayed there and would stay again. " [](https://expedia.ca/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information) ![Royal Regency Hotel](//images.trvl-media.com/lodging/1000000/50000/40900/40814/c5903df6_y.jpg) ### Royal Regency Hotel 10/10 Excellent "It’s a very convenient hotel" [](https://expedia.ca/White-Plains-Hotels-Royal-Regency-Hotel.h40814.Hotel-Information) ![Hyatt Regency Greenwich](//images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg) ### Hyatt Regency Greenwich 10/10 Excellent "No" [](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information) ![Armoni Inn & Suites](//images.trvl-media.com/lodging/1000000/20000/12100/12036/5f0c23aa_y.jpg) ### Armoni Inn & Suites 10/10 Excellent "Good I like it" [](https://expedia.ca/Orangeburg-Hotels-Armoni-Inn-Suites.h12036.Hotel-Information) ![Sonesta Simply Suites Nanuet](//images.trvl-media.com/lodging/1000000/700000/694300/694250/a9ba8283_y.jpg) ### Sonesta Simply Suites Nanuet 10/10 Excellent "great place for the price " [](https://expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.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 "Attentive staff clean hotel, and probably the best elevators I’ve ever encountered in any building of any type. " [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.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 "Desk clerk was very friendly, knowledgeable and thorough. " [](https://expedia.ca/Stamford-Hotels-Norwalk-Inn.h15114.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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