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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.

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Court House in Pittsfield

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Frequently asked questions

How much does it cost to stay in a 4-star hotel in Pittsfield?
With Expedia's handy search filters, landing a terrific deal on a 4-star hotel in Pittsfield just got simpler. Start by entering your chosen travel dates and length of your stay. Then sort the results by price and pick a property that best suits your budget and style.

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What's the difference between 5-star and 4-star hotels in Pittsfield?
If you decide to vacation at a 4-star hotel in Pittsfield, you'll usually find loads of conveniences to ensure you're relaxed, such as a pool, gym and restaurant. You can experience high-quality service and deluxe accommodations. Opt for a 5-star hotel and you'll have access to a few more bells and whistles — think on-site spas, 24-hour front desk and indulgent turndown services. You'll most likely get extra amenities and premium services at a 5-star getaway, though both are terrific options for luxury travelers.
Does Pittsfield have any 4-star all-inclusive resorts?
Finding your dream resort in Pittsfield is as simple as entering your travel dates and clicking on our "All inclusive" filter. Stay and play where everything is already taken care of like your accommodations, meals, activities and entertainment, or opt for a standard 4-star resort in or around this much-loved destination.