Title: Book the Best HISTORIC Hotels in Chester in 2025 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6046665.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6046665.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6046665.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6046665.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 Chester, 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 Chester Historic Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6046665&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=6046665&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester 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) ![Reception](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/383ffb6e.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) ### Overlook Lodge at Bear Mountain Bear Mountain 8.4/10 Very good (1014) "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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f57ee72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f3387c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/w3831h2553x9y7-9c25ee45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/8529e0e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Fishkill Fishkill 8.6/10 Excellent (1002) "Nice place" CA $177 CA $200 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/ab271dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/04adf8dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/c6f43c54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/97dee96b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer Beacon 10/10 Exceptional (44) "Great room and location. A nice home base for exploring the area. " CA $154 CA $341 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-4-On-Main-Street-Luxury-Steam-Shower.h69240003.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/67801e28.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 $425 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/28000000/27690000/27682300/27682249/1cd1ebc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27690000/27682300/27682249/84330e95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27690000/27682300/27682249/c62a123a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27690000/27682300/27682249/c05354d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf Vernon 9.8/10 Exceptional (87) "Such a magical property! I came here with some friends for my birthday weekend and we had the most incredible time. The space- both indoors and out, is even more beautiful than the pictures (which never happens!). Everything was very clean and well kept. And the property manager was very supportive and communicative throughout. Providing lots of helpful information beforehand, and stayed in touch during my stay, even over the smallest things. We came during the summer but would love to come back... CA $1,298 CA $2,457 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Vernon-Hotels-Ski-InSki-Out-Luxury-For-18-WHot-TubMnt-CreekHeated-PoolPrivate-Tennis-Crt.h27682249.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=6046665&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Hampton Inn & Suites Mahwah](//images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/c56a5aff_y.jpg) ### Hampton Inn & Suites Mahwah 10/10 Excellent "Close EV charging and parking. Staff was friendly and helpful." [](https://expedia.ca/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.Hotel-Information) ![The Crossroads Hotel, Newburgh](//images.trvl-media.com/lodging/1000000/20000/14500/14410/5440914b_y.jpg) ### The Crossroads Hotel, Newburgh 10/10 Excellent "Yes " [](https://expedia.ca/Newburgh-Hotels-The-Crossroads-Hotel.h14410.Hotel-Information) ![Quality Inn & Suites Fishkill South near I-84](//images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/12805cb0_y.jpg) ### Quality Inn & Suites Fishkill South near I-84 10/10 Excellent "Great " [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.Hotel-Information) ![Overlook Lodge at Bear Mountain](//images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Clean comfortable room. Bed was very comfortable. Hotel was quiet " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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 "AC works✅ Heat works✅ Hot water✅ Clean room✅" [](https://expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) ![Crowne Plaza Suffern - Mahwah by IHG](//images.trvl-media.com/lodging/1000000/10000/2400/2358/e31233cf_y.jpg) ### Crowne Plaza Suffern - Mahwah by IHG 10/10 Excellent "Marvellous stay at this wonderfully equipped, convenient hotel. Front desk staff were delightful (shout out to Yvonne!), friendly as well as competent and efficient. Infinitely more suitable for our business trip than the weird and wanting airbnb options we have tried in the area. Thank you, Crown Plaza!" [](https://expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](//images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "Great Views, very convenient " [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Days Inn by Wyndham Nanuet / Spring Valley](//images.trvl-media.com/lodging/1000000/180000/172100/172075/2336337b_y.jpg) ### Days Inn by Wyndham Nanuet / Spring Valley 10/10 Excellent "good" [](https://expedia.ca/Nyack-Hotels-Days-Inn-By-Wyndham-Nanuet-Spring-Valley.h172075.Hotel-Information) ![Hampton Inn Nanuet](//images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/af6569cb_y.jpg) ### Hampton Inn Nanuet 10/10 Excellent "Location " [](https://expedia.ca/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) ## Frequently asked questions ### What should a history buff expect from a stay in Chester? > You're already probably planning a visit to historical sites during your trip to Chester. During your stay, you can visit the shops and restaurants. ### How many historical hotels will I find in Chester? > In Chester, you'll find 19 lodging options bookable on Expedia though not many historic hotels to choose from. ### What are the top historical sites and other places to visit in Chester? > Chester is notable for landmarks like Museum Village. In the area, you'll also find LEGOLAND® New York and Woodbury Common Premium Outlets. ### What is a historic hotel like in Chester? > When you book a historic hotel, you'll sleep in a building that has an officially recognized national historic designation. A castle, a palace or even a pub or an old police station can be considered a historic hotel provided that it has special significance. Traditional architecture and period features can be admired within the guestrooms or public spaces of these historic hotels in Chester, giving a historical feel. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is more common in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. though overall the terms are quite similar. The architecture and building of historic hotels are generally the most important aspect. For a heritage hotel, mainly, it's cultural value as well as how it inspired the community. ### Do historic hotels in Chester have modern facilities? > Hotels have the safety features and modern conveniences you might expect, but every effort is made to preserve historic facades and treasured traditions. Smart TVs, WiFi, updated bathroom facilities, and the amenities found in most hotels should be available at a historic hotel. 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