210 West Street, P.O. Box 1920, Lenox, MA  01240-4920

800.966.3429 / 413.637.3429

The following is a quick note about our policies and procedures.

First and foremost, the booking system is from a 3rd party.  Consequently it does not easily handle the situations that are unique to each reservation.  If your needs fit into its box, then it'll work well for you.  If you have specific needs, it will probably not serve you well.  In that case, please, please call us directly.

During summer months we have a 3-night minimum during the weekends (Thursday - Sunday). You may choose whichever 3 nights you desire. Also, we offer a free 4th night's stay (subject to availability) in conjunction with the 3-night stay. We do not have a minimum stay midweek (Monday - Wednesday). We offer a free 3rd night's stay (subject to availability) in conjunction with a 2-night midweek stay.

All of this aside, we do make exceptions to our policy. As you can imagine, it would be almost impossible to conjure all the situations for an online booking system.  For example, the system does not allow for a 2-night weekend stay. But we welcome the opportunity to try to arrange it for you.  Also we do have a limited number of single-night stays available during weekends.

The Chesapeake Inn's strength is the personal attention that we provide you. This starts with the arrangements for your reservation. Again, we encourage you to contact us directly if you are having any difficulty with the automated system.


If you have interest in a package of multiple nights, please call for the best rate.