Title: The Best 5 Star Hotels in Chatham, NY from $114 | Expedia.com [Chatham Travel Guide](https://expedia.com/Chatham.dx6046736)[Hotels in Chatham](https://expedia.com/Chatham-Hotels.d6046736.Travel-Guide-Hotels)[Vacation Rentals in Chatham](https://expedia.com/Chatham-Vacation-Rentals.d6046736.Travel-Guide-VacationRentals)[Flights to Chatham](https://expedia.com/Cheap-Flights-To-Chatham.d6046736.Travel-Guide-Flights)[Car Rentals in Chatham](https://expedia.com/Car-Rentals-In-Chatham.d6046736.Car-Rental-Guide)[Chatham Vacation Packages](https://expedia.com/Chatham.d6046736.Destination-Travel-Guides) ![Tracy Memorial Village Hall, Chatham, New York](https://images.trvl-media.com/place/6046736/7198abd1-0904-483a-a024-c143d8de9574.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6046736/7198abd1-0904-483a-a024-c143d8de9574.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chatham 5 Star Hotels Tonight [Feb 22 - Feb 23](https://www.expedia.com/Hotel-Search?regionId=6046736&startDate=2026-02-22&endDate=2026-02-23&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 23 - Feb 24](https://www.expedia.com/Hotel-Search?regionId=6046736&startDate=2026-02-23&endDate=2026-02-24&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=6046736&startDate=2026-02-27&endDate=2026-03-01&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=6046736&startDate=2026-03-06&endDate=2026-03-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Chatham-Hotels.s50-0-d6046736.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Chatham-Hotels.s50-0-d6046736.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Chatham. ![The Wick, Hudson, A Tribute Portfolio Hotel](https://images.trvl-media.com/lodging/20000000/19750000/19742700/19742697/924e2902_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Wick, Hudson, A Tribute Portfolio Hotel 41 Cross Street Hudson NY $184 nightly $208 total Mar 4 - Mar 5 Total with taxes and fees 8.6/10 Excellent! (551 reviews) [](https://expedia.com/Hudson-Hotels-The-Wick.h19742697.Hotel-Information) ![The Central Downtown Inn & Suites](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/fdeb3407_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Central Downtown Inn & Suites 20 W Housatonic St. Pittsfield MA $102 nightly $114 total Feb 24 - Feb 25 Total with taxes and fees 8.6/10 Excellent! (357 reviews) [](https://expedia.com/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![Lakehouse Inn](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Lakehouse Inn 615 Laurel St. Lee MA $151 nightly $168 total Feb 28 - Mar 1 Total with taxes and fees 9.6/10 Exceptional! (292 reviews) [](https://expedia.com/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) Still don't see what you're looking for? [See all properties in Chatham.](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F23%2F2026&endDate=2%2F24%2F2026®ionId=6046736&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F23%2F2026&endDate=2%2F24%2F2026®ionId=6046736&star=50&star=50&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F23%2F2026&endDate=2%2F24%2F2026®ionId=6046736&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F23%2F2026&endDate=2%2F24%2F2026®ionId=6046736&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F23%2F2026&endDate=2%2F24%2F2026®ionId=6046736&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F23%2F2026&endDate=2%2F24%2F2026®ionId=6046736&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Chatham This charming upstate village hosts the Mac-Haydn Theatre's summer productions and a vibrant Main Street with independent shops and cafés. Explore the historic Union Station or time your visit for the Columbia County Fair, a beloved local tradition since 1841. [See all hotels in Chatham](https://www.expedia.com/Hotel-Search?startDate=2026-03-08&endDate=2026-03-09&adults=2®ionId=6046736) ![Tracy Memorial Village Hall, Chatham, New York](https://images.trvl-media.com/place/6046736/7198abd1-0904-483a-a024-c143d8de9574.jpg?impolicy=fcrop&w=320&h=400&p=1&q=high) ## Top Chatham Hotel Reviews ## Find out more about Chatham There's nothing wrong with enjoying the finer things in life. Add an extra layer of pleasure on your next trip to Chatham by treating yourself to the best of the best when it comes to lodging. It's an ideal fusion. There's no reason to delay a getaway to Chatham any longer. You'll join the multitudes of vacationers who have made Chatham so fashionable in the last few seasons. We should also mention, the hotels in this area are known for guest services, so you know you'll be well cared for during your getaway. What are you waiting for? Book one of Expedia's luxurious 5-star hotels in Chatham and get ready to enjoy the getaway of a lifetime. ### Get a Great Deal on 5-Star Hotels in Chatham Don't be afraid to be pampered during your trip, along with pristine rooms. Spa treatments, delicious meals, and one-on-one attention are all waiting for you. You're sure to find exactly the accommodation you need. Not only that, the hotels in this area receive noteworthy marks for guest services, so you know you'll be well cared for during your getaway. What creature comforts do you want in your lodging? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A body scrub that will leave you feeling like a million bucks? Butler services? Whatever it is your heart desires, you're bound to find it here. You won't sleep and order room service the entire time, though. We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Chatham are waiting for you to relax after an exciting day. Ready to learn more? Plenty of visitors recommend this location. ### Make Your Escape The results are in, and Chatham 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. Expedia can help you land a great deal on accommodation. It's time to plan your next great escape. Decide on one of our Chatham 5-star hotels today and decompress in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Chatham? > - Search for the lowest price per night from $114 ### What makes a hotel 5 stars in Chatham? ### Are there any 5-star all-inclusive resorts in Chatham? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near The Mac-Haydn Theatre ](https://www.expedia.com/The-Mac-Haydn-Theatre-Hotels.0-l553248621532665231-0.Travel-Guide-Filter-Hotels) - [Ghent Hotels ](https://www.expedia.com/Ghent-Hotels.d3000448661.Travel-Guide-Hotels) - [Vacation Homes in Ghent ](https://www.expedia.com/Ghent-Private-Vacation-Homes.d3000448661-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Motels in Ghent ](https://www.expedia.com/Ghent-Motels.d3000448661-aaMotels.Travel-Guide-Accommodation) - [Hotels near Hudson Chatham Winery ](https://www.expedia.com/Hudson-Chatham-Winery-Hotels.0-l553248621532665230-0.Travel-Guide-Filter-Hotels) - 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