The Homestead

The Homestead The Homestead is a twelve-room boutique Inn nestled along the coastline in Madison, Connecticut.

The Homestead is comprised of 11 individual guestrooms, each with its own private bath. We offer several guest common areas, including a comfortable living room with a fireplace, spacious dining room, inviting sunroom, and a beauty salon (perfect for day-of wedding prep). We also offer extensive outdoor grounds with patios, two fire pits, and a deck. Our approach to hospitality is to be available

if you need us while still allowing you your space to enjoy the property and our beautiful coastline town. Our home is a wonderful place for extended families to get away together or couples looking to escape the city. Many businesses find the property to be a unique and accommodating setting for corporate retreats and meetings. The Homestead has been in operation by The Guardiano family for over 30 years and across 3 generations. The house was originally built in 1958 with extensive renovations being completed

We look forward to hosting you and providing you with a unique experience and exceptional service.

Unplanned trips make the best memories! With only a few rooms left this weekend, book now and say YES to a little sponta...
06/18/2026

Unplanned trips make the best memories! With only a few rooms left this weekend, book now and say YES to a little spontaneity ✨

🎉🐾 Happy 5th birthday to our beloved canine in charge here at The Homestead! Today we celebrate Heartman for all the joy...
06/16/2026

🎉🐾 Happy 5th birthday to our beloved canine in charge here at The Homestead! Today we celebrate Heartman for all the joy and mischief he brings to our lives. Drop your birthday wishes for Heartman in the comments below and we promise to share them with him after he finishes his cake and ice cream 🎂🥳

💗 We love Madison, and we’re proud of our community! That’s why our Madison friends and neighbors always save 10% on sta...
06/13/2026

💗 We love Madison, and we’re proud of our community! That’s why our Madison friends and neighbors always save 10% on stays here at The Homestead. Stop by and say HI 👋 anytime 😊

MadisonCT

🧳 Oh, the tales a little stuffed animal can tell! After a recent guest checked out, we made a delightful discovery: Mr. ...
06/11/2026

🧳 Oh, the tales a little stuffed animal can tell! After a recent guest checked out, we made a delightful discovery: Mr. Strutton Pigeon stayed behind at The Homestead to continue enjoying his stay.

This curious critter has been having a whirlwind of adventures around our B&B, cozying up in our luxury linens, DJ-ing his favorite tunes on our rockin’ record players, leading a sing-along in our living room, frolicking in our gardens, and trying his hand (his wings are surprisingly good) at a game of shuffleboard. Mr. Strutton Pigeon is living his best life!

We’ve been in touch with his human, and we’re trying to talk him into taking the train home, but he’s not ready to leave just yet – who can blame him?



🎓 It’s Graduation time and we love it when friends and families stay with us for special occasions. Our door is open but...
06/10/2026

🎓 It’s Graduation time and we love it when friends and families stay with us for special occasions. Our door is open but we only have a few rooms left so don’t delay - book your stay today!

🎓

🎈A special offer for our special friends. So special, you'll need to call us to reserve your stay. Your chair is ready,...
06/05/2026

🎈A special offer for our special friends. So special, you'll need to call us to reserve your stay. Your chair is ready, and we can't wait to see you!

06/03/2026
🥁 Madison’s Memorial Day parade is a long-standing tradition tied to our town’s patriotic history. Its roots can be trac...
05/23/2026

🥁 Madison’s Memorial Day parade is a long-standing tradition tied to our town’s patriotic history. Its roots can be traced back to the post-Civil War era. The annual parade begins at 10 a.m. on Monday at the intersection of Samson Rock Drive and Boston Post Rd and proceeds west through downtown, concluding with a remembrance ceremony at the Town Green and a flyover.

This holiday we pause to remember the fallen with great gratitude.

Address

391 Boston Post Road
Madison, CT
06443

Telephone

+12032450212

Website

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