Homestead Of Madison
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Each of our ten guestrooms features a beautifully renovated spacious private bathroom, Smart TV, and vintage-style record player. Each room has a unique personality, from bright and airy with private entrances to a kid-friendly cowboy room. The town of Madison, CT is home to two beautiful beaches on the CT Shoreline and boasts over 2 miles of beach!

Our quaint downtown includes an arts cinema, local giftshops and the #1 independent bookstore in the country. The CT Shoreline is the perfect Fall spot for pick-your-own adventures. We are are home to several local spots for apple and pumpkin picking--not to mention fresh cider! From beachy boardwalk strolls to quintessential New England color filled forests, our location offers hikers the best of New England.
Services
We provide a private and comfortable environment that is perfect for small companies and executives to clear their minds. Whether you need a brainstorming session or a spot for a sleep study, we can accommodate your group's unique needs.

Main Dining Room and Adjoining Sun Room (with seating for 13 across one large table and 3 smaller tables), Living Room with Gas Fireplace, Two Outdoor Gas Fire Pits, Three Outdoor spaces for Entertaining, Hair Salon, and Extensive Outdoor Grounds.The house has 10 rooms for overnight guests and breakfast is included with every stay.
Reviews (9)
Joshua Norton
Joshua Norton
Jan 24, 2022
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Extremely welcoming and explaining what was the property and what was where. Was extremely clean. Really close to Madison center really pretty area
Svetlana Zakharina
Svetlana Zakharina
Oct 12, 2021
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I really enjoyed my long weekend stay at The Homesteam a few days ago. Very clean, quiet, and pleasant Inn. Nice size rooms and bathrooms are newly renovated, friendly staff and beautiful outdoor area. Definitely will be back. Thanks!
Diana Rucci
Diana Rucci
Jul 26, 2021
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My best friend and I recently stayed at the Homestead for a few days. This was our first time in Madison Connecticut, what a wonderful place. From the moment we arrived at the Homestead until we left, the staff was personable and attentive; everyone had such a warm personality. Even the owner, Ralph, found time to chat with us and provided great restaurant and daytrip recommendations.
The room was immaculate with so much attention to detail. All the little things made the stay so enjoyable. The scenery was also beautiful; such a quiet and peaceful environment. I especially enjoyed having my coffee
Alyssa Cioffi
Alyssa Cioffi
Jun 02, 2021
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The staff was incredible! So kind and accommodating! We would definitely stay again. It was a walkable distance to the beach which is also beautiful! We loved coming back and being able to sit outside our room and sitting outside near the fire pits!
David Armstrong
David Armstrong
Dec 02, 2020
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I had the pleasure of staying at The Homestead on a recent business trip. Wow! The Inn/B&B setting was a wonderful change. Where to begin...
Entering my room, I was greeted by "Lucky" the duck and a personal note welcoming me. The room was spacious with an extremely comfortable bed with first class linens and towels. The room came with a turntable and records which brought back lots of memories. The room was a great retreat when I needed some time by myself.
The common spaces provided wonderful places to explore the magazines, books, pictures and games available. They also provided great spaces
Melissa Goldberg
Melissa Goldberg
Sep 24, 2020
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Ralph and his staff were incredibly thoughtful and hospitable but most importantly, took excellent and smart measures to make sure everyone was safe and comfortable during these crazy times. We were itching to have a short getaway from the city but were hesitant because of COVID. After looking at a few lodging accommodations, we were sold on The Homestead ultimately because they indicated all the precautions they were taking because of COVID on their website which made us feel very comfortable, particularly knowing all their cleaning protocols and that no one would be in our room for at least 24
Jose Ortiz
Jose Ortiz
Sep 02, 2020
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We had a great stay! Owner and staff were extremely friendly and helpful! Breakfast was great! Rooms are beautiful as well as property! We will definitely be coming back!
Jesbri
Jesbri
Nov 20, 2019
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This place is magical, very cozy and house keeper Damaris is awesome, made us feel at home...Great job Homestead...😊
Ray Bickford
Ray Bickford
Jul 10, 2018
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Absolutely the best B&B experience of my life. The attention to detail paid to every aspect of of the rooms was exceptional. The staff and breakfast they provided every morning were amazing. Honestly everything was over the top exceptional from the fire pit out front to the offer of free bikes with baskets to ride downtown or to the great little bar called the "Wharf" right down the street.
If your lucky enough run into the owner Ralph its worth your time time to try and get him to tell you one of the many story's about the place. Not only is he personally an exceptional story teller but his family