Stay on the Shoreline / The Homestead

Where will you find The Homestead? Imagine driving down historic Boston Post Road, with glimpses of roadside farmer’s markets, peeks of the Long Island Sound, and the quaint downtown of Madison filled with local restaurants, shops and cafes. Make a quick turn down a gravel road, lined with mature trees shading the path to a beautiful bed and breakfast, with bright red Adirondack chairs welcoming you to the property. There you will find The Homestead Bed & Breakfast.

The Homestead has been in operation by the Guardiano family for over 30 years and across 3 generations. The family’s history runs deep, and so does their hospitality and individual care of each guest. The Homestead sets the perfect balance between a welcoming bed and breakfast making you feel instantly at home, while allowing you the privacy of your own suite. The residence has 10 individual bedrooms, each with their own private bathroom, three having their own private entrance. Simply reserve a room, or the entire residence for up to 16 guests, making The Homestead the perfect option when hosting a seaside wedding.

The charm of the Shoreline is felt in every aspect of The Homestead. Whether it’s the classic guest key, the individuality of each suite, or the fact that they take the time to ask you your favorite music selections prior to your stay. This is because you’ll find a record player in each room, with the music you personally requested, inviting you to put on a record and immediately unwind, detach from your everyday, and breath in the salty air of the Shoreline.

homestead bed

The Homestead invites you to unwind, because they’ve thought of everything. Whether it’s the amenities in your room, access to coffee, drinks and snacks throughout the day, beach passes to enjoy the nearby Surf Club, or beach cruisers perfectly affixed with Nantucket woven baskets to take you where you want to go. Or stay right where you are and pull up a red rocking chair to their fire pit and roast marshmallows while taking in the views of their tree-lined entrance.


Whatever your reason for stopping in, The Homestead will ensure your stay is filled with Shoreline charm, the best hospitality possible, and a true understanding of why there’s no place like Shoreline Connecticut.

The Homestead
391 Boston Post Road
Madison, CT 06443
(203) 245-0212

homestead bed
homestead bed