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.

🥁 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.

👑The annual "Best on The Shoreline" competition is here. Please help us hold onto our crown!  Use the link below to vote...
05/21/2026

👑The annual "Best on The Shoreline" competition is here. Please help us hold onto our crown!

Use the link below to vote daily until Sunday, June 7, 2026, and we promise to provide experiences that keep you coming back for more! 🥰
Category: Night & Day>Inn or Bed & Breakfast
https://zip06.com/best-on-the-shoreline/ #/gallery?group=538999

Thank you from all of us at The Homestead!

Follow us on TikTok! 😎☀️
05/20/2026

Follow us on TikTok! 😎☀️

Watch, follow, and discover more trending content.

🎷🎹Here at The Homestead Bed and Breakfast, music isn't just background noise; it's the very heartbeat of our haven of ho...
05/17/2026

🎷🎹Here at The Homestead Bed and Breakfast, music isn't just background noise; it's the very heartbeat of our haven of hospitality. Dive into a world where every corner sings with harmony. 🎻🎺🎸🥁 From instruments ready for your passionate serenade to a treasure trove of albums for every musical whim. Plus a record player in every room tuned to your very own musical taste!

Come stay with us and let the symphony of relaxation begin!

Follow us and be part of our melodious journey.

Your cozy weekend escape is calling… and we’ll be by the phone ready to book your stay! 📚
05/14/2026

Your cozy weekend escape is calling… and we’ll be by the phone ready to book your stay! 📚

🌸 Mother-Daughter getaway alert! We loved having these ladies join us for a delightful getaway at The Homestead. Our Chi...
05/12/2026

🌸 Mother-Daughter getaway alert! We loved having these ladies join us for a delightful getaway at The Homestead. Our Chief Canine Officer Heartman is still standing by the door waiting for them to come back! 🐾

🎁Still wondering what to give your Mom on Sunday?  Treat her to a summer getaway at The Homestead Bed and Breakfast in t...
05/06/2026

🎁Still wondering what to give your Mom on Sunday? Treat her to a summer getaway at The Homestead Bed and Breakfast in the delightful coastal New England town of Madison, CT. Nestled amongst blooming flowers and lush landscapes, our cozy haven of hospitality invites her to unwind and indulge in pure bliss.

Picture this: 🌞morning sunshine streaming through the window, ☕a fragrant cup of coffee in hand, and delicious locally-made 🥐 breakfast goodies to savor. Later, she can explore the quaint shops in the town of Madison or kick back in a comfy chair with a good book on one of our outdoor patios or at one of the best stretches of beach in the state.

Give her a well-deserved escape. Call us at 203.245.0212 or book her a getaway on our website, www.homesteadmadison.com, and we will be sure she’s taken care of. We can help you make this Mother’s Day one she'll treasure forever!

04/30/2026

At The Homestead, we don’t let gloomy days get to us… we just grab a blanket and lean into the cozy 🔥

04/28/2026

What’s better than the sound of popcorn popping? The SMELL! 🍿

04/24/2026

POV: you’re pulling up the driveway to stay at your favorite weekend escape, The Homestead!

With only a few available rooms left this weekend, this can be your view too!

Happy Valentine’s Day from our family-run B&B! Sending lots of love to our guests, friends and family❤️ (pic features ou...
02/14/2026

Happy Valentine’s Day from our family-run B&B! Sending lots of love to our guests, friends and family❤️ (pic features our 2nd-4th generation)

Address

391 Boston Post Road
Madison, CT
06443

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