Title: 5 Stars Hotels in Pittsfield, Illinois  - Find Cheap Pittsfield Hotels With 5 Stars | Expedia.ca

[Pittsfield Travel Guide](https://expedia.ca/Pittsfield.dx146411)[Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d146411.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d146411.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d146411.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d146411.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d146411.Destination-Travel-Guides)

![Court House in Pittsfield](https://images.trvl-media.com/place/146411/e1162892-98db-4e1f-aa10-c1e92fa5be83.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Pittsfield 5 Star Hotels

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[Feb 22 - Feb 23](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2026-02-22&endDate=2026-02-23&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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## Learn more about Pittsfield

Nestled among rolling hills, Pittsfield invites history buffs to explore the John Greene Shastid House and Pike County Historic Museum. After delving into local heritage, visitors can unwind with a peaceful afternoon at King Park or tee off at nearby Old Orchard Country Club.

[See all hotels in Pittsfield](https://www.expedia.ca/Hotel-Search?startDate=2026-03-08&endDate=2026-03-09&adults=2&regionId=146411)

![Court House in Pittsfield](https://images.trvl-media.com/place/146411/e1162892-98db-4e1f-aa10-c1e92fa5be83.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high)

## Top Pittsfield Hotel Reviews

## Find out more about Pittsfield

## Five Star Hotels in Pittsfield

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 Pittsfield 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 Pittsfield and get ready to be pampered like never before.

#### Get a Great Deal on 5-Star Hotels in Pittsfield

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 Pittsfield

The results are in, and Pittsfield 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 Pittsfield! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Pittsfield 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 Pittsfield?

> - Search for the lowest price per night

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

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

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