Deciding where to stay during your visit to the Berkshires largely depends on the purpose of your stay, how long you’ll be there, what you want to see, and the vibe you’re going for so there’s no definite answer to the best place to stay in the Berkshires. If you’re looking to be in the center of the action and within walking distance of many attractions, consider Great Barrington, Lenox, or Stockbridge. If you want more rural, but still a short drive to the best of the Berkshires, we love New Marlborough, Stockbridge, Egremont, and Richmond.
And if you’re looking for a cozy cottage, we recommend Oak Hill House, our lovingly restored cottage in New Marlborough.