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

4 Star Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield 4 Star Hotels

Next weekend
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul

Our top choices for Pittsfield 4-star hotels

Front of property – evening/night

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (639 reviews)
"Great property and restaurant. Perfect location and very helpful, friendly staff."
United States
Sam
The price is €312
includes taxes & fees
27 Jul - 28 Jul
The Williams Inn
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (373 reviews)
"Easy access to parking, nearby everything and room was very clean. Definitely will come back here to stay again! "
United States
Aisha
The price is €114
includes taxes & fees
7 Jul - 8 Jul
The Central Downtown Inn & Suites
Suite, Private Bathroom (RedBird Suite) | View from room

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (112 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is €349
includes taxes & fees
19 Jul - 20 Jul
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

Seven Hills Inn

Seven Hills Inn
4.0 star property
Lenox
7.8 out of 10, Good, (467 reviews)
"Great location, nice breakfast and clean rooms"
United States
Christopher
Seven Hills Inn
Luxury Room, 1 King Bed, Bathtub

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is €719
includes taxes & fees
23 Jul - 24 Jul
33 Main
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is €429
includes taxes & fees
13 Jul - 14 Jul
Devonfield Inn B&B
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is €393
includes taxes & fees
20 Jul - 21 Jul
The Inn at Stockbridge
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (303 reviews)
"Clean rooms and staff were very knowledgeable about the area. Breakfast was very good. Beautiful room and view on second floor. Would recommend as a place to get away from it all!!"
United States
Angela
Lakehouse Inn
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is €259
includes taxes & fees
7 Jul - 8 Jul
Hampton Terrace Inn
Apartment (4 Bedrooms) | Interior

Family-friendly Hancock Home: Walk to Slopes!

Family-friendly Hancock Home: Walk to Slopes!
4.0 star property
Hancock
Family-friendly Hancock Home: Walk to Slopes!
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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.

See all hotels in Pittsfield
A historic building with a clock, a flag, and a street lamp.

Top Pittsfield Hotel Reviews

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

8/10 Good
"We had a good stay here. The suite was clean. The building was quiet. Management was responsive. We did find it odd that there was no front desk, and everything was done by phone, but perhaps that's the modern way. We would definitely stay here again."
Kathryn 1-night trip
Posted 19 hours ago
The Central Downtown Inn & Suites

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 customers. Concierge services and designer toiletries are a couple of its amenities. Travellers also love staying at Hampton Terrace Inn. From a swimming pool to premium bedding, it offers conveniences that cater to all aspects of your relaxation and entertainment.
How much does it cost to stay in a 4-star hotel in Pittsfield?
With Expedia's handy search filters, locking in a top deal on a 4-star hotel in Pittsfield just got easier. Start by keying in your chosen arrival date and length of your getaway. Then sort the results by price and pick a hotel that best matches your style and budget.

  • Search for the lowest price from €114

What's the difference between 5-star and 4-star hotels in Pittsfield?
If you decide to stay at a 4-star hotel in Pittsfield, you'll usually find lots of amenities to ensure you're comfortable, such as a pool, restaurant and gym. You can enjoy high-quality service and upscale surroundings. Opt for a 5-star hotel and you'll have access to a few extra bells and whistles — think on-site spas, concierge assistance and nightly turndown services. You're likely to get additional amenities and exclusive services at a 5-star stay, though both are superb options for luxury travellers.