The Homestead

The Homestead in Madison is a home away from home (if your home is a stunning mansion on the CT coastline). If you don’t have the time or resources to make it to Santorini or Bora Bora this year, do as we do and book a one-night luxury getaway in your own backyard (or state!). You’ll actually be saving money. ?

Post sponsored by The Homestead

Ah, The Homestead. From the moment we drove up its long driveway, we were captivated. This ten-room inn nestled off of Boston Post Road in picturesque Madison is convenient to several nearby beaches, boutiques, and excellent restaurants. We’ll get to all of that in our next post, “Day Tripping in Madison”. But first, here’s The Homestead!

Pillars, red doors and Adirondack chairs, wreaths, and bows = Madison charm

The Homestead Welcome

We arrived around 3 PM and met the three lovely ladies who run the show. Owner Ralph Guardiano was out of town, so, unfortunately, we didn’t get to meet him (next time!). After a quick tour of the 10 bedrooms (each with their own charm and private bathrooms), we decided it was wine o’clock and enjoyed a glass of red by the fire. Relaxing already.

You’ll find interesting antiques throughout the house 

The Homestead’s approach to hospitality is to be available if needed, but for the most part, it’s “make yourself at home.” And so, when Anne, Pat, and Damaris left us with another bottle of wine and snacks to enjoy, we took our shoes off and kicked back by the fire. For about ten whole minutes (you know we can’t sit still for too long!)…

Evening activities

It happened to be “Ladies Night Out” in Madison that night which involved shopping and cocktails. To avoid FOMO, we pried ourselves away from the cozy fireplace and were glad we did! The ladies of Madison are fun! Downtown during Christmas is something straight out of a Hallmark movie, especially when a gaggle of carolers passed us on the street. 

At Christmas time… 

A couple of silly hours later, we were back at “our” house, again sitting by the fire in the living room. 

After remembering that neither of us plays the piano, we decided a sing-a-long to one of our favorite Christmas numbers was in order. The Homestead provides a record player in each room (brilliant), which we knew in advance and had packed some 80s gems. 

And at a rocking 10 PM, it was time to retire to our rooms, or to our floors rather. We decided to take a floor each, because we could.

We really, really appreciate when hotels and inns provide a black towel ??


The rooms are all unique and sport their own Nantucket vibes. 1,000 thread count sheets, plush towels, The Body Shop toiletries, a mini-fridge, bottled water, and a box of local chocolates on the pillow were just a few of the things that made us want to extend our stay for an extra month or two. 


Breakfast was served by Pat at a pre-arranged time. Needless to say, it was 1,000 times better than my usual two pieces of toast and Lora’s usual protein shake. 

These Bloody Marys were every bit as good as they look
As was this quiche…
And these yogurt parfaits


The Homestead has free bikes for their guests to use along with free beach passes. They’ll even set you up on a bicycle made for two and a picnic basket to make a day of it. For the record, we only made it down the driveway and back…it was cold. And we needed practice… 

In the warmer months, you can grab a kayak and they’ll help you get across the road for a paddle on the Long Island Sound. We may just have to go back to check that out! 

To sum it up, The Homestead is a perfect coastal B&B to unwind and enjoy a luxurious stay in a relaxed atmosphere. The entire house can be rented out and would make for a perfect backdrop for wedding preparations, family gatherings, or corporate retreats.  

Thank you, Homestead! 

The Homestead 

391 Boston Post Road, Madison, CT 06443


Pics: Lora/ Words: Bev

This post has been sponsored

Join the Conversation

Leave a Reply

Your email address will not be published. Required fields are marked *

© Copyright 2022. All rights reserved.