Title: The Best 5 Star Hotels in Chesterfield, MA from $111 | Expedia.com

[Chesterfield Travel Guide](https://expedia.com/Chesterfield.dx89029)[Hotels in Chesterfield](https://expedia.com/Chesterfield-Hotels.d89029.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.com/Chesterfield-Vacation-Rentals.d89029.Travel-Guide-VacationRentals)[Flights to Chesterfield](https://expedia.com/Cheap-Flights-To-Chesterfield.d89029.Travel-Guide-Flights)[Car Rentals in Chesterfield](https://expedia.com/Car-Rentals-In-Chesterfield.d89029.Car-Rental-Guide)[Chesterfield Vacation Packages](https://expedia.com/Chesterfield.d89029.Destination-Travel-Guides)

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## Check availability on Chesterfield 5 Star Hotels

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[Mar 10 - Mar 11](https://www.expedia.com/Hotel-Search?regionId=89029&startDate=2026-03-10&endDate=2026-03-11&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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## 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/2000000/1460000/1457800/1457797/4092a889_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$99 nightly

$111 total

Mar 11 - Mar 12

Total with taxes and fees

8.6/10 Excellent! (358 reviews)

[](https://expedia.com/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information)

Still don't see what you're looking for?

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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

There's nothing wrong with enjoying the finer things in life. Add an extra layer of pleasure on your next trip to Chesterfield by treating yourself to the best of the best when it comes to accommodation. It's an ideal pairing. There's no reason to delay a getaway to Chesterfield any longer. You'll join the multitudes of vacationers who have made Chesterfield so fashionable in the last year. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. 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

You'll have a wonderful time at one of these 5-star hotels. High-end restaurants, excellent customer care, and deeply relaxing spa offerings are waiting for you. You're sure to find exactly the accommodation you need. You'll also enjoy a high standard of care and meticulous guest relations, so get ready to kick back and indulge. What creature comforts do you want in your lodging? A concierge to help you make reservations at that outstanding restaurant? A full-body massage to help your cares fall away? High thread-count sheets, delectable chocolate desserts, and even space for your family pet in some cases...these hotels have it all. 

Can't wait to get outside? 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 you end up doing, the 5-star hotels in Chesterfield are waiting for you to relax after a busy day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs. 

### Your Getaway Starts Today

The results are in, and Chesterfield 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. It's time to plan your next great escape -- Expedia can help you land a great deal on accommodation. Decide on one of the 5-star hotels in Chesterfield today and settle down in complete comfort when you're ready.

## 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 $111

### What makes a hotel 5 stars in Chesterfield?

### Are there any 5-star all-inclusive resorts in Chesterfield?

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