Pittsfield Vacation Homes

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

In two weeks

In two months

In three months

In four months

Our top choices for Pittsfield holiday homes

A wooden deck with a table and chairs, surrounded by a white railing.

1. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

HK$3,890 total

includes taxes & fees

27 Oct - 28 Oct

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

2. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

HK$9,431 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

3. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Joanna P.

HK$1,631 total

includes taxes & fees

27 Oct - 28 Oct

A spacious living room with a dining area, a kitchen, and a large window.

4. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

HK$1,766 total

includes taxes & fees

5 Nov - 6 Nov

A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

5. Ellie’s Overlook, best view in the Berkshires!

Richmond

HK$5,420 total

includes taxes & fees

2 Nov - 3 Nov

A white two-story house with a porch, surrounded by trees and a hill.

6. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

HK$3,405 total

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

7. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

Robert B.

HK$4,666 total

includes taxes & fees

12 Nov - 13 Nov

8. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

HK$4,281 total

includes taxes & fees

26 Oct - 27 Oct

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

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

Top Pittsfield Hotel Reviews

Hotel On North

10/10 Excellent

"Big spacious rooms, great bed, great bath."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Property is on a little lake and we had a balcony room with view of the lake. I can imagine it must be great to have in the warmer months, but we enjoyed the view nonetheless. Everything was clean, staff was friendly, the restaurant food we sampled was very good, the jet tub was much appreciated, and the location was perfect for exploring all of the quaint towns in the Berkshires. The nightly rate was very reasonable."

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