Find 4 Star Hotels in Pittsfield, MA from $158

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Compare Pittsfield 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

The Williams Inn
Front of property - evening/night
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (344)
"Excellent location and, modernized, a great improvement over previous property since demolished "
The price is $324
includes taxes & fees
$290 per night
Oct 21 - Oct 22
The Williams Inn
Lakehouse Inn
Aerial view
Lakehouse Inn
4.0 star property
9.8 out of 10, Exceptional, (200)
"Just a beautiful hotel with a most welcoming staff"
The price is $158
includes taxes & fees
$142 per night
Sep 22 - Sep 23
Lakehouse Inn
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites
4.0 star property
8.8 out of 10, Excellent, (255)
"Good price quality ratio"
The Central Downtown Inn & Suites
Devonfield Inn B&B
Front of property - evening/night
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (113)
"Wonderful place for a quiet getaway for a couple of nights. Scenic setting. Delicious breakfasts, helpful owners and staff on site. We'd book again!"
The price is $390
includes taxes & fees
$349 per night
Sep 23 - Sep 24
Devonfield Inn B&B
Seven Hills Inn
Terrace/patio
Seven Hills Inn
4.0 star property
7.8 out of 10, Good, (467)
"Great breakfast, amazing property, comfortable beds! Water in shower wasn’t hot, had to take a “warm-cold” fast shower but it didn’t matter. The view, the quiet, nature and siting areas made the stay perfect. Will come again!!"
Seven Hills Inn
The Barrington
Junior Suite | Premium bedding, individually decorated, desk, iron/ironing board
The Barrington
4.0 star property
9.8 out of 10, Exceptional, (106)
"Wonderful stay. Beautifully appointed rooms, comfortable bed, hot shower, quiet and restful. Lovely touches, but the best part of all is the incredible breakfasts prepared by French chef and manager William. Having these to look forward to each morning was a joy. Highly recommend this excellent property!"
The price is $363
includes taxes & fees
$325 per night
Sep 27 - Sep 28
The Barrington
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main
4.0 star property
10.0 out of 10, Exceptional, (67)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is $492
includes taxes & fees
$440 per night
Sep 26 - Sep 27
33 Main
The Inn at Stockbridge
Exterior
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (95)
"Well-run and elegant property. "
The Inn at Stockbridge
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Suite, Private Bathroom (RedBird Suite) | View from room
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (103)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is $555
includes taxes & fees
$497 per night
Sep 22 - Sep 23
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Hampton Terrace Inn
Seasonal outdoor pool
Hampton Terrace Inn
4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
Hampton Terrace Inn
Garden Gables Inn
Front of property - evening/night
Garden Gables Inn
4.0 star property
9.2 out of 10, Wonderful, (57)
"Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. "
Garden Gables Inn
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Frequently asked questions

What are the best 4-star hotels in Pittsfield?
Garden Gables Inn is a 4-star hotel in Pittsfield that’s popular among Expedia travelers. A terrace and premium bedding are some of its many amenities. Travelers also recommend Hampton Terrace Inn. From a swimming pool to premium bedding, it features conveniences that cater to all aspects of your relaxation and enjoyment.
How much does it cost to stay in a 4-star hotel in Pittsfield?
To lock in a 4-star hotel in Pittsfield that matches your budget, use Expedia’s search and sort filters. Check out the available options during your getaway dates and use our pricing filter to set your maximum rate. You can also sort your results by the cheapest stay first.

  • Search for the lowest price from $158

What's the difference between 5-star and 4-star hotels in Pittsfield?
Treat yourself to refined living during your Pittsfield escape by checking in to a 4-star hotel. As well as featuring upscale surroundings, these retreats are usually filled with amenities such as large beds, complimentary bathrobes and more. A 5-star hotel will go the extra mile to make your stay an even more indulgent and unforgettable one. 24-hour concierge assistance, luxurious spas and world-class dining are just the start of the exclusive conveniences and services you’ll likely get access to.
Does Pittsfield have any 4-star all-inclusive resorts?
One of the quickest ways to look for your ideal Pittsfield retreat is to use our “All inclusive” filter tool. You can also search for other leading 4-star options such as Hampton Terrace Inn and Garden Gables Inn. Both include exceptional service and plenty of conveniences for your enjoyment and relaxation.
Are there any 4-star casino hotels in Pittsfield?
Shuffle between your room and the roulette wheel with ease by using our filters to find 4-star casino hotels in and around Pittsfield. Escaping with someone special? Refine your search further by selecting amenities with a wow-factor, like a pool or view.