The Red Lion Inn | Stockbridge, Massachusetts

The Red Lion is a historic inn that has been operating for over two hundred years and provides a fantastic base for exploring the beautiful Berkshires area.

Offering guests a variety of dining options, entertainment every night, a heated outdoor pool and hot tub, The Red Lion is also eco-sustainable. It has an elegant dining room, a tavern for casual food and drinks, and a pub that is a live music venue every night. Accommodation is available in the Main Inn, but also in the Red Lion Guest Houses, a group of village houses located close to the Inn, each with their own entrance and private driveway.


The Main Inn – Rooms on offer include Deluxe, Superior and Suites, all which offer a private bathroom and variety of bed configurations including king, two queens or doubles. The Superior Rooms and Suites are the most spacious. The Suites have a separate living area with a sofa bed, so are perfect for both couples who want a bit more space, and families.

The Guesthouses – Each guest house unit is configured differently, with varying features. Some have kitchen facilities, others have a screened porch, living area, dining area or second bedroom. The guest houses are dotted around Stockbridge village, some very near the Main Inn, but others, like Meadowlark, once the studio of sculptor Daniel Chester French, are situated a short drive away from the Inn.

Why We Like It

The Red Lion Inn is a unique and eclectic property that offers guests an inviting environment, whether staying in the Main Inn or in one of the Guesthouses. The nightly live music is a reason in itself to book a few nights there!

Services and Amenities

New York to Toronto – 2015 (Smith)

I have just returned from a tailor made holiday made possible by Jeannette Dembrey. This was the first time I had ever organised such a major holiday and as it was a gift for my children after my retirement it was really important to get things right. I went to quite a few agencies but Jeannette was way better than any of the people who I spoke to. She was so professional and wanted me to get the best from the money I could afford. The holiday was absolutely amazing and everything went like clockwork. Jeannette had thought of everything even the connections between places and the things we would do in each town. We stayed in 6 hotels altogether starting in New York and ending in Toronto. I am amazed at how smoothly it went. Even my son who has travelled all over the world was impressed with the way things had been organised. I cannot praise Jeannette enough for her professionalism. Thank you Jeannette. I would recommend you to anyone with the satisfaction of knowing that you did an amazing job. Thank you.

J Smith - Travelled New York to Toronto