5 Stars Hotels in Pittsfield

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Check availability on Pittsfield 5 Star Hotels

Tonight
28 Dec - 29 Dec
Tomorrow
29 Dec - 30 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
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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 Pittsfield.
The Williams Inn

The Williams Inn

101 Spring Street Williamstown MA
The price is ฿6,797 per night from 1 Jan to 2 Jan
฿6,797
฿7,592 total
1 Jan - 2 Jan 2026
includes taxes & fees
9.6/10 Exceptional! (554 reviews)
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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.

Learn more about Pittsfield

Nestled in the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.

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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Pittsfield?
The amount you pay for a 5-star hotel in Pittsfield depends on things such as when you plan to go and the length of your trip. An insider tip for landing an awesome deal? Use our pricing filters to compare all of the available accommodation for your chosen dates.

  • Search for the lowest price per night from ฿3,259

What makes a hotel 5 stars in Pittsfield?
Exemplary guest service is the foundation of every 5-star hotel in Pittsfield. From the minute you arrive, staff cater to your every whim, whether recommending activities and tours or providing a turn-down service. What's more, hotels have to feature upscale amenities to be eligible for a 5-star rating. These can include luxury bath products, on-site spa facilities, pools, gourmet kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Pittsfield?
Our convenient filters are the quickest way to search for exactly what you're looking for. Select "5-star" and "All inclusive" to show the finest properties in Pittsfield where your lodging, meals, entertainment and activities are included in the upfront price. At these escapes, your holiday is pure leisure from the moment you arrive.