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The Homestead Bed & Breakfast

391 Boston Post Rd, Madison, CT 06443-2934
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COVID-19 update: See the added health and safety measures this property is taking.Read more
Lowest prices for your stay
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Free cancellation until 05/18/21
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Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. Please see our partners for more details.
Traveler (49)
Room & Suite (21)
Videos (2)
What is Travelers’ Choice?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travelers and are ranked within the top 10% of properties on Tripadvisor.
Travel safe during COVID-19
Visit our Travel Safe hub to see how we're helping you make more informed travel decisions during COVID-19.
What you can expect during your stay
  • All linens sanitized in high-temperature wash
  • Face masks required for guests in public areas
  • Face masks required for staff in public areas
  • Floors marked for social distancing
  • Hand sanitizer available to guests & staff
  • Paid stay-at-home policy for staff with symptoms
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Updated 02/25/21 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
A note from The Homestead Bed & Breakfast
Updated 02/25/21 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.


#1 of 6 B&Bs / Inns in Madison
Travelers' Choice
Boutique Accommodations with Comfortable Luxury and Unimposing Hospitality. The Homestead offers unique New England charm with easy access to beaches, shopping, and restaurants along the Connecticut coast in Madison. Each of our 10 guestrooms features a private bath, vintage-style record player & vinyl collection, and complimentary wireless internet access. Select guestrooms feature private entrances with outdoor seating areas or electric fireplaces. Whole house bookings are available, making The Homestead an excellent gathering space for corporate retreats, group events, or family holidays. We have complimentary vintage-style bicycles complete with picnic baskets, extensive grounds with beautiful gardens, and two on-site firepits. The Homestead is a perfect for getaway for travelers looking for a boutique experience without the fussiness of traditional Bed and Breakfast properties. Located off of I-95 and less than two miles to the Train Station, Madison is a great spot for travelers looking to escape the city or stopover for those exploring the East Coast.
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Room & Suite (21)21
Full view
Property amenities
Free parking
Free High Speed Internet (WiFi)
Free breakfast
Children Activities (Kid / Family Friendly)
Pets Allowed ( Dog / Pet Friendly )
Breakfast available
Bicycle rental
Bicycles available
Board games / puzzles
Non-smoking hotel
Outdoor fireplace
Outdoor furniture
Picnic area
Shared lounge / TV area
First aid kit
Private check-in / check-out
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Room features
Air purifier
Air conditioning
Wardrobe / closet
Bottled water
Private bathrooms
Cable / satellite TV
Bath / shower
Tile / marble floor
Flatscreen TV
Complimentary toiletries
Hair dryer
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Room types
Non-smoking rooms
Family rooms
Good to know
Languages Spoken
English, German
94Reviews0Q+A20Room tips
Traveler rating
  • 94
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Time of year
Traveler type
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Popular mentions
M H wrote a review Apr 2021
3 contributions2 helpful votes
The inn keepers were gracoius and welcoming. The Inn had taken many precautions against Covid 19. The setting was beautiful with many options for sitting outside. The rooms were tastefully decorated and the bathrooms spa like
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Date of stay: April 2021
Sleep Quality
Room Tip: Room 14 ans 15
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jcreature wrote a review Oct 2020
New York City, New York174 contributions28 helpful votes
Property's Favorite Review
As a travel writer who is accustomed to bouncing all over the world, the pandemic has really been difficult psychologically. So I developed a plan after three months of lockdown in NYC: I would rent a car each month for a 3-night stay in a scenic location no more than 2 hours from New York City. I had so many conditions before any accommodation made the cut for me. The innkeeper had to be very COVID conscious, they had to be over-the-top warm and welcoming when I spoke with them prior to making my reservation on the phone, the room had to either have a separate entrance or have access to a patio/terrace, and the inn had to be close to green spaces, beaches or other places to hike, walk and enjoy the outdoors. Of all the places I’ve stayed so far, the Homestead in Madison is the supreme winner. I fell in love with my room #7: its white-on-white palette is fresh and refreshing; the mattress is firm and so comfortable I didn’t want to get out of bed; the windows allowed the sun to stream into the room that provided views of nothing but nature. The shower head offers a fine mist like actual rain — it was so delightful, I want to buy one for my house. (Same for the mattress and pillows.) The property offers about nine different places outside to sit and relax, whether it’s an isolated bench under a shade tree or at a table where I could work on my iPad outside, and just enjoy the views of the lawn, flowers and birds that are frequent visitors. (I brought a bottle of wine with me and I fell in love with having a glass each afternoon in the garden.) The staff couldn’t be more accommodating, including leaving wine glasses for us, providing utensils for out takeaway meals that we ordered in town, and making coffee just the way I like it. Everyone here, including the owner, Ralph, really cares about the accommodation — it’s been family owned for decades — and the guest’s experience. I’m as picky as they come regarding accommodations — well, actually regarding most everything — and this is an inn that I will return to again and again. I’m already planning my next trip in a couple of months. I wish all innkeepers were as caring as they are at the Homestead.
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Date of stay: October 2020
Room Tip: I loved my room: #7. It’s quiet, sunny and it’s a corner room on the first floor. Love, love,...
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Response from Ralph Guardiano, Owner at The Homestead Bed & Breakfast
Responded Nov 1, 2020
Hi Jeanine, Thank you for your kind words. It was a pleasure meeting you. Here at The Homestead we strive to make our guest's stay as safe and enjoyable as possible. We hope to welcome you again, winter in New England is always very picturesque! Have a safe holiday. Thank you again, The Staff at The Homestead
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Margaret M wrote a review Feb 2021
1 contribution
From the moment we drove up the majestic driveway we could feel the stress and tension from life, work, and covid meltaway. Ralph, the Innkeeper met us in the driveway (mask on) and assisted us with our luggage. We were given a tour of the stately home decorated with antique cameras and vintage record players and albums. The Homestead has a warmth and ambiance with soft lighting that makes anyone look good. The rooms are large with like a zillion thread count sheets and extremely comfortable mattresses. The shower even has a shower head with infused zen-like pixie dust raining down on you. Relaxing and chatting in front of the fireplace was a favorite way to spend the evenings. Musical instruments, including piano, were available to enjoy as well. In a nutshell, I highly recommend The Homestead if you are looking for unsurpassed hospitality and a place to put your feet up for a while and head home feeling like a million bucks!
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Date of stay: January 2021
Jennie A wrote a review Nov 2020
1 contribution
My stay was very relaxing. The room was spotless and the property was beautiful. I felt safe and pampered. The staff and owner were kind and mindful of the current pandemic. The location is located near beaches, restaurants, and the downtown area. I highly recommend the Homestead.
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Date of stay: November 2020Trip type: Traveled solo
Don T wrote a review Nov 2020
1 contribution
Ralph and his staff leave out not one detail. The house is beautiful, clean and filled with fun antiques. Each room has record player and actual vinyl albums based on the music you prefer. The COVID virus does not stand a chance in this place. Everywhere precautions have been taken to combat any germs. The house is in a great location between Madison and Guilford, and the area is a beautiful gem. Beautiful shoreline, beaches, old homes, cute villages with great restaurants. HIGHLY recommend the Homestead.
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Date of stay: November 2020
Sleep Quality
$188 - $366 (Based on Average Rates for a Standard Room)
United StatesConnecticutMadison
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Frequently Asked Questions about The Homestead Bed & Breakfast
Which popular attractions are close to The Homestead Bed & Breakfast?
Nearby attractions include RJ Julia Booksellers (1.1 miles), Hammonasset Beach State Park (2.9 miles), and Bishop's Orchards (4.2 miles).
What are some of the property amenities at The Homestead Bed & Breakfast?
Some of the more popular amenities offered include free wifi, free breakfast, and free parking.
Which room amenities are available at The Homestead Bed & Breakfast?
Top room amenities include air conditioning, a flat screen TV, and a refrigerator.
What food & drink options are available at The Homestead Bed & Breakfast?
Guests can enjoy free breakfast during their stay.
Is parking available at The Homestead Bed & Breakfast?
Yes, free parking is available to guests.
What are some restaurants close to The Homestead Bed & Breakfast?
Conveniently located restaurants include Bar Bouchee, Lobster Landing, and Rocky's Aqua.
Is The Homestead Bed & Breakfast located near the city center?
Yes, it is 0.7 miles away from the center of Madison.
Are pets allowed at The Homestead Bed & Breakfast?
Yes, pets are typically allowed, but it's always best to call ahead to confirm.
Which languages are spoken by the staff at The Homestead Bed & Breakfast?
The staff speaks multiple languages, including English and German.
Are there any historical sites close to The Homestead Bed & Breakfast?
Many travelers enjoy visiting Hyland House Museum (3.3 miles).