The Homestead, A Review: Quirky Haven in Madison CT

The Homestead – A Boutique Inn in Madison Connecticut

When I tire of upscale, “design by committee” corporate hotels, I look for something that deviates from the norm. Not so much as to be unrecognizable as an inn, or glitzy, or flamboyant. Just a place that showcases the creative chops of its owner. And I found all that at The Homestead Madison CT.

The Homestead grounds in Madison CT

Ralph Guardiano and his daughter are the second and third generation to own this inn, first built as a retirement home in 1958.

Recently reopened after a complete renovation of the inn’s 12 rooms, it is homey, unpretentious, and oh so idiosyncratic. That’s owing to the fact that Guardiano owns a production and marketing company – a career that takes him around the world – and he has a tendency to pick up objects that catch his eye.

First Impressions of The Homestead Madison CT

Approaching the whitewashed inn, you’ll see a handful of bright red Adirondack chairs on the front lawn. It’s an inviting tableau – red against white, shade trees, and a front porch with a fire pit and more red chairs. Welcoming, and slightly quirky.

Exterior of The Homestead Madison CT

The quirkiness ramps up when you walk inside. If it’s cool out, the gas fireplace in the main parlor is blazing, and over it, a picture frame “TV” that showcases a rotating roster of Guardiano’s favorite paintings. Together, they bathe the room, stocked with an assortment of early 60’s-style overstuffed furniture, in a flickering glow.

Parlor at The Homestead Madison CT

There’s a cacophony of curio objects all over the place. Guardiano evidently loves rubber duckies and antique cameras and photo equipment. And radio microphones.

Curio shelf at The Homestead Madison CT

Have the innkeeper (or Ralph, if he’s there) point out the teeny-tiny styrofoam cup that was full size before being sent to the depths of the Atlantic – to the wreck of the Titanic. It shrunk down to nearly nothing from the water pressure, and stayed that way.

Lucky Duckys at The Homestead Madison CT

Even prior to arriving, you get the feeling that whoever owns the place is eager to please.  You’re asked about any dietary restrictions – pretty typical for a B&B.

And then, the peculiar query about music preferences. Why? Because among the many categories of things that Guardiano collects are vinyl records – and record players.

Record player in guest room at The Homestead Madison CT

So, yes, there’s a turntable in each guestroom – complete with vinyl records of your favorite bands.

Rooms at The Homestead

Guest Room #2 at The Homestead Madison CT

All 12 rooms are different, with eclectic furniture, art, and knickknacks that can change depending on Guardiano’s gleanings that week.

Private entrance to guest room at The Homestead Madison CT

Some on the ground floor (like mine #2) have private entrances. Some have two beds for families, mother-daughter, or girlfriend getaways.  Three are pet-friendly.

But all rooms have several things all the time. One is the most dreamy sinkable bedding that, in my case, sent me off into an uninterrupted 7 hours of sleep. Another is the aforementioned record player and records. And yet another is a set of little rubber “Lucky Ducks” and mini ducky marshmallows (so much better than Peeps) that you get to take home.

And, all bathrooms sport a futuristic toilet with warm seat, and bidet on demand. And, get this – shower water is filtered 15 times, and infused with vitamins that left my skin and hair so soft.


Even though The Homestead does not have a restaurant, you will NOT go hungry here. There’s a popcorn machine – with both infused oil and dry shaker toppings to give the snack pizzazz. Bags of premium potato chips and granola bars are left out for the taking.

And, in the morning, breakfast around the communal table invites conversations among guests. (Always a perk when I’m traveling alone). The Homestead sources from the best of local bakeries, and serves those muffins and other baked goods along with a fruit salad and hot savory dish of the day. (Mine was a toothsome slice of quiche).

Cheese Plate enhancement The Homestead Madison CT

To make it uber romantic, order an “Enhancement” ahead of time. (For a fee) you can have a beautiful cheese plate waiting in your room, perhaps with a chilled bottle of Prosecco.

Just the Facts

Rooms start at $235 midweek off-season, and rise to $440 per night weekends in season. $515 for 2-bedroom family suite. Includes gourmet breakfast, treats, snacks, boxes of water, use of beach-cruiser bikes, mini-duckies. The “Elopement Package” for couple and up to 4 witnesses includes a local officiant, 6” cake, and champagne toast, $650 (does not include room).

Care to explore around? Check out out Madison CT and Nearby Clinton post, and neighboring Guilford CT.

And, check this post out for more Romantic Hotels in CT.

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  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine,, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

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