Pittsfield Guest Houses

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Pittsfield guest houses

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

1. The Central Downtown Inn & Suites

Pittsfield

HK$867 total

includes taxes & fees

2 Nov - 3 Nov

A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

2. Berkshire Village Carriage House - Super Private!!

Lanesborough

Mary R.

HK$1,498 total

includes taxes & fees

2 Nov - 3 Nov

A large white house with a prominent tower, surrounded by lush greenery and a well-maintained lawn.

3. Hideaway Inn Lenox

Lenox

Barbara

HK$981 total

includes taxes & fees

2 Nov - 3 Nov

A living room with a fireplace, two sofas, and four black side tables.

4. The Revival House

Adams

Katrina

HK$1,210 total

includes taxes & fees

9 Nov - 10 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Pittsfield Hotel Reviews

The Red Lion Inn

10/10 Excellent

"The rooms are so unique and cozy, the food was excellent and and the staff was so helpful- Olivia from the front desk went above and beyond while Nellie from housekeeping happily assisted me at the ice machine as I struggled- i love the place so much."

Quality Inn Great Barrington

10/10 Excellent

"This motel was exactly what we were looking for during our short stay. It was clean comfortable and easy to access. The bathroom toilet flushing mechanism was a bit slow/occasionally needed two flushes. There are train tracks behind the building and there is a train that will come by at night that is relatively loud. The breakfast had warm options and was satisfactory. Limited fresh fruit options but overall met our needs. I would stay here again and maybe request the front of the building to limit train noise."

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good

"We had a good stay the staff when I arrived was super nice and personable and we really like the amenities. I really like the water that was filtered in the front and the breakfast was very good choices. Our room was very clean and the TV selection was great."

Find out more about Pittsfield