The Homestead

The Homestead The Homestead is comprised of 11 individual guestrooms, each with its own private bath.

Named the No. 4 winner in USA Today’s 2026 10Best Bed & Breakfasts in America contest, The Homestead is in the charming coastal town of Madison, near one of the state’s most beautiful beaches. 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 extensiv

e 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.

🏠 The Homestead is just a building without the incredible people inside it. 💗Happy National Hotel Employee Day! Here are...
09/01/2026

🏠 The Homestead is just a building without the incredible people inside it. 💗Happy National Hotel Employee Day! Here are the amazing faces behind our spotless rooms, great coffee, and unforgettable stays. We appreciate everything they do!

Heartman has officially joined the decorating committee.His first recommendation?Dogs everywhere.His second?Coffee. Lots...
08/29/2026

Heartman has officially joined the decorating committee.

His first recommendation?
Dogs everywhere.

His second?
Coffee. Lots of coffee.

We’re still working on the budget for his design plan. 🐾☕️😂

08/26/2026

🐾In honor of National Dog Day, Heartman commissioned a sculpture of himself—because, in his view, every day should be dog day! Aug. 26 offers a chance to celebrate the special bond between humans and their dogs. The day also promotes dog ownership across all breeds and reminds us how much joy dogs bring to everyday life. Heartman’s new sculpture reinforces his belief that dogs deserve the spotlight year-round, and yes, we agree with him. 👍

08/23/2026

☀Summer isn’t over yet! There’s still time to soak up the sunshine and make the most of the season, from relaxing beach days to scenic hikes, wine tastings, antique shopping, and farm stand finds.

Consider this your sign to squeeze in a few more summer adventures and explore all our little slice of heaven has to offer.

08/12/2026

🙌 The votes are in and we’re overjoyed to report that The Homestead won #4 in the the USA Today’s 10Best Bed and Breakfasts in the nation! Thank you for your support, we couldn’t do what we do without you 😊.

https://10best.usatoday.com/awards/best-bed-and-breakfast/

🌻The sunflowers that bloom in Connecticut are reaching their peak right now! By early August, many spring and early-summ...
08/05/2026

🌻The sunflowers that bloom in Connecticut are reaching their peak right now!

By early August, many spring and early-summer flowers have finished blooming, so acres of brilliant yellow sunflowers create a dramatic burst of color across the landscape.

Connecticut has several famous sunflower fields. One of the best-known is less than an hour away, at Buttonwood Farm in Griswold. It is spectacular to see the hundreds of thousands of sunflowers in bloom each summer. And if that wasn't enough, get their ice cream! With 50 flavors, their premium ice cream is made in small batches; this is the ultimate summer day trip 🍦❣

Closer to Madison, you'll find Lyman Orchards Sunflower Maze in Middlefield. Guests can wander through over 350,000 blooming sunflowers. This year's maze is carved into a special design featuring Winnie-the-Pooh holding "100" balloons, surrounded by buzzing bees and storybook charm.

These fields are a photographer’s dream. The combination of towering flowers, blue August skies, and warm evening light makes Connecticut’s sunflower fields especially popular for photography, painting, and family outings.

Come for the sunflowers and stay at The Homestead for an unforgettable summer memory.

Join us on TikTok as we start sharing life at The Homestead!
08/05/2026

Join us on TikTok as we start sharing life at The Homestead!

Watch, follow, and discover more trending content.

08/03/2026
💗💓 Our hearts are full thanks to the wonderful reviews we have received from our guests over the past few days. We love ...
07/28/2026

💗💓 Our hearts are full thanks to the wonderful reviews we have received from our guests over the past few days. We love what we do, but knowing that our guests return the feeling makes it even better 🥰

Address

391 Boston Post Road
Madison, CT
06443

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