Pittsfield Chalets

Upfront pricing

Our total price for your stay includes taxes and fees

Treat yourself

Save 10% or more on over 100,000 hotels worldwide with Member Prices

Learn about One Key

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Chalets in Pittsfield

Relax on the deck with a view of the lush landscape, featuring a comfortable sofa and outdoor seating area.

"Our stay was great. The property was extremely clean and the host was absolutely amazing. The property is located on a pond which we could kayak and do some fishing. Just sitting on the beautiful deck overlooking the pond was relaxing. The property offered exactly what we were looking for for this trip. "

Relax in the backyard hot tub surrounded by serene natural scenery and a patriotic touch.

"Rimon and Sallie's place is fantastic. Very clean with everything we needed for our stay. The kids were able to have their own separate space, and the common areas were great for food prep and sitting down for meals. The kids loved the hot tub and were in 3 separate times (even in the freezing temps!).The house is very private on a beautiful road, and is a short drive to Troy, Albany, etc. We had a great dinner at Hill Creek Tavern 5 minutes from the house. I would absolutely recommend this...

Two single beds with white duvets, a wooden staircase, and a large mirror adorn this inviting bedroom.

"Short couples getaway to recharge. The house was perfect and the wood stove kept the house toasty through the cold windy stay. HINT: coming from NY/NJ, buy your groceries as you pass through Great Barrington and save that extra trip."

Relax in this spacious living room with a comfortable seating area, large windows, and a sloped ceiling.

Situated on a hill, this house offers expansive views of the surrounding forested hills.

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

Top Pittsfield Hotel Reviews

Holiday Inn Express & Suites Pittsfield - Berkshires

10/10 Excellent

"The hotel was 4-weeks old - so the room had that "new" smell. We were there for an evening stopover driving into Boston from Toronto with kids. Thus, having a working indoor pool was important. Parking was amply available and the free breakfast was a god-send since it helped us save a few bucks with the terrible exchange rate us Canadians have to contend with! Over time, we hope that more food options will appear as we were disappointed with Arizona's Pizza down the street, even with the discount. But that's a review for another time and space!"