Title: 5 Stars Hotels in Chesterfield, Massachusetts from CA $138 - Find Cheap Chesterfield Hotels With 5 Stars | Expedia.ca [Chesterfield Travel Guide](https://expedia.ca/Chesterfield.dx89029)[Hotels in Chesterfield](https://expedia.ca/Chesterfield-Hotels.d89029.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.ca/Chesterfield-Vacation-Rentals.d89029.Travel-Guide-VacationRentals)[Flights to Chesterfield](https://expedia.ca/Cheap-Flights-To-Chesterfield.d89029.Travel-Guide-Flights)[Chesterfield Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterfield.d89029.Car-Rental-Guide)[Chesterfield Vacation Packages](https://expedia.ca/Chesterfield.d89029.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Chesterfield, Massachusetts from CA $138 - ![](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 Chesterfield 5 Star Hotels Tonight [Dec 5 - Dec 6](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2025-12-05&endDate=2025-12-06&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 6 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2025-12-06&endDate=2025-12-07&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2025-12-05&endDate=2025-12-07&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2025-12-12&endDate=2025-12-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chesterfield 5 Star Hotels ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Chesterfield-Hotels.s50-0-d89029.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Chesterfield-Hotels.s50-0-d89029.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 Chesterfield. ![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 CA $123 CA $138 total Dec 10 - Dec 11 includes taxes & fees 8.6/10 Excellent! (346 reviews) [](https://expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) Still don't see what you're looking for? [See all properties in Chesterfield.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F12%2F2025&endDate=08%2F12%2F2025®ionId=89029&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F12%2F2025&endDate=08%2F12%2F2025®ionId=89029&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F12%2F2025&endDate=08%2F12%2F2025®ionId=89029&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F12%2F2025&endDate=08%2F12%2F2025®ionId=89029&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F12%2F2025&endDate=08%2F12%2F2025®ionId=89029&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F12%2F2025&endDate=08%2F12%2F2025®ionId=89029&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. ## Top Chesterfield Hotel Reviews ## Find out more about Chesterfield ## Five Star Hotels in Chesterfield There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Chesterfield so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Chesterfield and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Chesterfield Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Chesterfield The results are in, and Chesterfield 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. This is a great time to find 5-star hotel deals in Chesterfield! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Chesterfield today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Chesterfield? > - Search for the lowest price per night from CA $138 ### What makes a hotel 5 stars in Chesterfield? ### Are there any 5-star all-inclusive resorts in Chesterfield? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [2 Star Hotels in Allston ](https://www.expedia.ca/2Star-Allston-Boston-Hotels.s20-n73196-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in East Village Historic District ](https://www.expedia.ca/2Star-East-Village-Historic-District-Amherst-Hotels.s20-n553248621557920008-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in South End ](https://www.expedia.ca/2Star-South-End-Springfield-Hotels.s20-n898868902485037056-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Foxboro ](https://www.expedia.ca/3Star-Foxboro-Hotels.s30-0-d8136.Travel-Guide-Filter-Hotels) - 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