Find 4 Star Hotels in Pittsfield, MA from $95

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

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (548)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
$186 nightly
The price is $208
Dec 14 - Dec 15
Total with taxes and fees
The Williams Inn

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
$85 nightly
The price is $95
Dec 10 - Dec 11
Total with taxes and fees
The Central Downtown Inn & Suites

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
$195 nightly
The price is $218
Dec 12 - Dec 13
Total with taxes and fees
Lakehouse Inn

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
$349 nightly
The price is $390
Dec 10 - Dec 11
Total with taxes and fees
Devonfield Inn B&B

Seven Hills Inn

4.0 star property
Lenox
7.8 out of 10, Good, (467)
"Great location, nice breakfast and clean rooms"
United States
Christopher
Seven Hills Inn

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
$414 nightly
The price is $462
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$441 nightly
The price is $493
Jan 8 - Jan 9, 2026
Total with taxes and fees
33 Main

General Williams Estate House Lenox/Stockbridge

4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (111)
"The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot."
United States
Joanna T.
General Williams Estate House Lenox/Stockbridge

Hampton Terrace Inn

4.0 star property
Lenox
9.0 out of 10, Wonderful, (43)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
$263 nightly
The price is $294
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hampton Terrace Inn

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
$263 nightly
The price is $294
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Inn at Stockbridge

Garden Gables Inn

4.0 star property
Lenox
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. "
United States
john
Garden Gables Inn
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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.

Pittsfield featuring a city

Top Pittsfield Hotel Reviews

Find out more about Pittsfield

The preparation of any holiday kicks off with picking a destination. Pittsfield has been a popular local with travelers because of everything it offers. But, "location, location, location" applies to more than just your destination. Now that you have got a feel for Pittsfield, it is time you to learn a little more about your new digs.

Accommodations as Scenic as the City

Pittsfield saw its fair share of visitors this past year. And plenty of these people submitted comments which may help you determine the accommodation that is the right fit for your trip. Spending the night in an accommodation with an overall score of 3.6 can only help to make your trip better. The staff ensure that the grounds and facilities are orderly, so you enjoy your stay no matter what area of the hotel you are in. You'll be more than glad to come back to the property each night. Pittsfield has several phenomenal lodgings that offer the perfect holiday.

A stay at one of these resorts makes certain that whether you are just taking a break after a day of sightseeing in Pittsfield or you're ready to lie down for the evening, you'll be as comfortable as imaginable. You won't have to go without a thing throughout your stay at one of these accommodations. Visitors have consistently praised them for their attentive service. It's not a surprise that a large majority of reviewers recommend it.

Reserve a 4-Star Hotel in Pittsfield Today!

Your getaway to Pittsfield should be one where you don't have to trouble yourself about the little things. Make sure to make a reservation soon. With so few lodgings, and so many people wishing to vacation in here, you may miss the chance to reserve your perfect hotel.

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 $95

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.

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