Hotels in The Berkshires

Pittsfield is the most commonly searched city in The Berkshires by momondo users. Prices for hotels in Pittsfield are typically $175/night. Other popular cities in The Berkshires include Lenox($317/night) and Lee($179/night).

The following hotels are the top rated hotels in The Berkshires: 9.8 - Granville House in Great Barrington, 9.7 - The Inn at Richmond in Richmond and 9.4 - The Inn at Stockbridge in Stockbridge

The Yankee, Trademark Collection by Wyndham is the most popular hotel in The Berkshires with a rating of 8.6/10 from 1,317 momondo users. In the past year, 8% of all users looking for hotels in The Berkshires booked a room at The Yankee, Trademark Collection by Wyndham.

Hotel prices throughout The Berkshires will vary depending on what city you plan to stay in, but in general you can expect prices in February to be around $174 per night on average for a double room. However our users have seen The Berkshires hotel prices in February for as low as $55 per night in the city of Lee.

Our data shows that hotel rooms in Stockbridge are about 13% more expensive on average than hotel rooms in the rest of The Berkshires, with a nightly rate of $234.

Our users typically find that Lee has the lowest nightly rates in the country at just $74. Lee offers hotel rooms at an average rate that is 65% lower than the average city in The Berkshires.

The Red Lion Inn, The Yankee, Trademark Collection by Wyndham and Jiminy Peak Mountain Resort are all hotels in The Berkshires that are good for families. $272 per night is the average price for a room at The Red Lion Inn, $94 per night is typical for The Yankee, Trademark Collection by Wyndham and $166 per night is the average rate for Jiminy Peak Mountain Resort.

Although room rates may vary depending on the time of year, these top three couples hotels in The Berkshires have the following average rates: $272 per night at The Red Lion Inn, $94 per night at The Yankee, Trademark Collection by Wyndham and $100 per night at Holiday Inn & Suites Pittsfield-Berkshires By IHG.

As of February 2026, there are 976 operators available to choose from for hotels in The Berkshires.

Prices for hotels in The Berkshires are updated daily.