Top Guest Houses in Pittsfield in 2026

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

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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

Rena

₹9,740 total

includes taxes & fees

3 Sept - 4 Sept

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

2. Hideaway Inn Lenox

Lenox

Ann

₹14,887 total

includes taxes & fees

7 Sept - 8 Sept

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

3. The Revival House

Adams

James

₹17,699 total

includes taxes & fees

20 Aug - 21 Aug

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Top Pittsfield Hotel Reviews

Berkshire Mountain Lodge

8/10 Good

"This hotel is a good option for Tanglewood concerts—only 15 minutes from the grounds, with nearby markets to grab food and wine along the way—but I would also consider going back with my family for another vacation. The room was large and had a separate bedroom and kitchenette/dining table, which aren’t easy to find and good for stays with kids. The indoor pool was large, and the game room looked cute. There is no food on site, which is the only main negative about this property. But there are plenty of options nearby."

Berkshires Untold

8/10 Good

"For the Berkshires, a nice, affordable option. Property has been updated, has some luxurious touches (le labo!), and is overall nicely designed. Food at the restaurant is delicious. The rooms could be a little bit cleaner, and the staff could have been a bit friendlier (but maybe they were just exhausted from a busy season). If you’re staying on the first floor, the a/c definitely works but dehumidification is kind of an issue. Overall, a good stay. Location is convenient to absolutely everything."