A historic building with classical architecture, a traffic light, and a yellow taxi.

Search Inns in Pittsfield

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Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Pittsfield inns

A dining table set for two with red plates, silverware, and a wine glass, viewed through a window overlooking a red building.

1. Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (153 reviews)
"The bed was soooo comfortable!"
United States
DONNA
$103 nightly
The price is $114
Oct 26 - Oct 27
Total with taxes and fees
Gregory House Country Inn
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.
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Top Pittsfield Hotel Reviews

Berkshires Untold

Berkshires Untold

8/10 Good
"My only complaint was that the restaurant was much smaller then appeared in pics. I also didn’t love having to walk outside to get to lobby. It was a very cold weekend when we were there"
Luann 2-night trip
Posted 2 hours ago
Berkshires Untold

Find out more about Pittsfield

Pittsfield Inns information

Number of reviews
153
Accommodation
5 Inns
Lowest Price
$114
Highest Price
$114

Frequently asked questions

How much do inns in Pittsfield cost?
Rates for inns located in Pittsfield range between $114 and $114 per night. Whatever your budget, you're sure to find somewhere comfy to relax and recharge your batteries. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly inns located in Pittsfield?
Yes, there sure are! Reserve a stay at Kemble Inn, a family-friendly inn only a quick drive from downtown Pittsfield. Offering conveniences such as complimentary breakfast and WiFi, the whole crew will feel at home at this reliable 3.5-star escape. Once you've checked in, there are plenty of family-friendly attractions to see in and around Pittsfield. Hancock Shaker Village and Berkshire Museum promise fun for all ages.
Why book your Pittsfield inn with Expedia?
Booking an inn in Pittsfield is as easy as working out your travel dates and choosing an option that suits your style. After something affordable or upmarket, or a property that also has a kitchenette? Use Expedia's search filters to further narrow your search results and find the perfect fit.
How can I find cheap Pittsfield inns?
Expedia will help you narrow your search for cheap Pittsfield inns. Simply enter your destination and travel dates and then use our filters to choose your preferred property star rating, budget and amenities. You can also search for your perfect inn based on popular locations and neighborhoods.
What is there to do in Pittsfield around my inn?
You'll find loads of fabulous things to do and see in Pittsfield. Explore major attractions like Bousquet Ski Area, Pittsfield State Forest and Barrington Stage Company. Berkshire Museum, Colonial Theater and Arrowhead Museum are also on many to-do lists.

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