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9.6

123 reviews

The Homestead

The Homestead

391 Boston Post Road, Madison, 06443, Connecticut, United States

Reservations:

+1-833-728-2041

Choose dates to view prices

Free Private Parking

Free wifi

Streaming service (like Netflix)

Air conditioning

Sun deck

Private entrance

Parking On Site

Terrace

The Homestead

Welcome to The Homestead, a charming 3-star Bed and Breakfast located at 391 Boston Post Road in the heart of Madison, Connecticut. Just 0.9mi away from the city center, you’ll find this cozy retreat a perfect blend of comfort and convenience. With 123 reviews praising its hospitality, The Homestead promises a delightful stay for every guest.

This pet-friendly establishment offers a range of thoughtful amenities to ensure a pleasant experience. From free wifi and air conditioning to beach umbrellas and loungers, The Homestead goes above and beyond to cater to your needs. Enjoy a leisurely day at the private beach or relax in the sun deck and garden areas. With free parking on-site, you can explore the beauty of Madison with ease.

Unwind in one of the non-smoking rooms with a private bathroom and free toiletries, while breathing in the fresh air purified by air purifiers. The Homestead’s picnic area and terrace provide the perfect spots to enjoy the surroundings. Whether you're here for a weekend getaway or a longer stay, The Homestead offers a delightful retreat for travelers seeking comfort and relaxation.

For guests traveling with their furry companions, The Homestead extends a warm welcome to pets. With pet-friendly accommodations available upon request, this charming Bed and Breakfast ensures that your four-legged friends can join in on the vacation fun. Please note that charges may apply for pet stays, so be sure to inquire about this when making your reservation.

Embracing a cash-only payment policy, The Homestead keeps things simple and hassle-free for its guests. In a digital age, this quaint approach adds to the unique charm of the establishment, allowing visitors to disconnect from the noise of everyday life and truly unwind in the serene surroundings of Madison, Connecticut.

Step into one of The Homestead’s cozy and well-appointed non-smoking rooms, each equipped with a private bathroom and complimentary toiletries. With air purifiers offering a breath of fresh air, you can relax knowing that every detail has been carefully considered to ensure a comfortable and rejuvenating stay. Whether you spend your days strolling along the private beach, basking in the sun deck, or exploring the nearby city center, The Homestead promises a tranquil retreat for travelers looking for a delightful escape.

Closest airports

Tweed-New Haven Airport

14mi

Long Island Mac Arthur Airport

42.2mi

Bradley International Airport

45.7mi

Westchester County Airport

58.7mi

Most popular amenities

Free Private Parking

Free wifi

Streaming service (like Netflix)

Air conditioning

Sun deck

Private entrance

Parking On Site

Terrace

Non-smoking rooms

Beach umbrellas

Beach chairs/Loungers

Patio

Picnic area

Garden

Free toiletries

View

Bidet

Bathtub

Rooms

Family Suite

+

More details

1 King Bed

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More details

1 King Bed Guestroom, 1st Floor

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2 Queen Beds Guestroom

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1 King Bed Guestroom, Bathtub, 1st Floor

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1 King Bed Guestroom

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Guest reviews

9.6

123 reviews

Categories of assessments

Cleanliness

Comfort

Location

Facilities

Staff

Value for money

WiFi quality

Breakfast

Featured reviews:

🇺🇸

Diane

10

May 2024

I have traveled around the world using Bookings.com and Airbnb, and this is by far the nicest Inn I've ever had the pleasure of staying in! The owners, staff, and resident dog, Hartman, were exceptionally welcoming and helpful. The breakfasts, which included freshly baked quiche and bread or pastry, fresh fruit salad, juices, and coffee or tea, were delicious and enjoyable as the guests gathered around the table each morning. Healthy and tasty snacks and drinks are available 24/7. Ellen went above and beyond in moving my room to a quieter side of the inn to make my puppy more comfortable.

🇺🇸

Betsey

10

March 2024

A wonderful experience!!!! They have thought of everything….pastries to greet us as we arrived, popcorn later in the afternoon, coffee and soft drinks at all times, a glass of Port before bed and a wonderful breakfast of a selection of quiche, croissants and muffins. The Inn is absolutely charming! The rooms are well decorated with high end touches even have record players in every room with an amazing collection of records to choose from…warm and welcoming common rooms and a fabulous staff who couldn’t do more to make us feel welcome!

🇺🇸

Scott

10

December 2023

Immaculate, charming, many extra little special details. The room had an air purifier, an electronic fireplace, electronic candles, both night stands with multi-outlet strips and a record player with assorted albums. Beautifully decorated rooms and facilities. Sitting rooms with eclectic and seasonal decorations. You could wander around enjoying all the special nick knacks. Tea, coffee, popcorn and baked snacks were provided. We both had colds and did not want to spread it at breakfast but look forward to our next visit to enjoy the full experience.

Nothing at all.

🇬🇧

Gary

10

September 2023

Superb!. From the moment we arrived until we left the experience at the Homestead was exceptional. Beautiful renovated house with large spacious rooms full of eclectic stuff collected by the owners. Spotlessly clean and had everything we needed and more including a fantastic vinyl record player with a massive selection of albums to play. The home downstairs had a gorgeous fire and a great place to relax and chat (with guests or the host). A fantastic popcorn machine, salted taffy on tap and a bottle of port for a nightcap all available for the guests. We had a lovely evening chatting to the host Ralph who was very engaging and made sure we had everything we needed. It was clear that he was proud of this family run business and wanted guests to partake of all they provide. Breakfast was lovely, simple but plentiful. Ellen and Ray were always on hand to make sure we had everything we needed and were attentive and friendly. A beautiful 2 nights and I end how I started, superb.

Nothing

🇺🇸

Melinda

10

August 2023

The Homestead was a perfect spot for exploring the perfect town of Madison. Just down the road is a lovely downtown area, perfect for walking around with shops, food, ice cream, entertainment, all with a safe, small town feel. The beach nearby was just beautiful with a shallow sandy bottom, mossy rocks, and a large nearby shady picnic area. Parking was very easy and convenient and a very close bathroom/outdoor shower was a huge bonus. The Homestead provided a beach pass which was a savings. Beach towels were loaned out too. Our room was spacious, clean, and there was even a bidet toilet seat! The rest of the inn was adorably decorated and the staff was very helpful. Overall, a wonderful experience!

The Homestead is a classic old home. Be prepared to lug your own luggage up a full flight of stairs to most rooms. Or specify a downstairs room which I did not know to do when booking. Parking is a bit tight when the inn is full. The grounds are well kept but the sign off the main road is very easy to miss. Might need more lighting on the sign at night.

🇺🇸

Diana

10

August 2023

This was hands down the best Bed and Breakfast we have ever been. The staff was so accommodating, the decor was cozy without feeling fussy, the bedroom amenities from linens to the select soaps were perfection and we look forward to returning. There were plenty of spaces to retreat together on the property, or to socialize with other guests. The Homestead approaches your stay with a detailed eye and interacts with you as little or as much as you wish. Special details like freshly popped popcorn, record players in each room, and even a birthday cake for all of us guests celebrating made our stay feel customized and homey. Ralph, Ellen, Ray and their mascot Heartman, were incredible. Highly recommend!

Nothing could be better. Everything was perfect! I wish we could have stayed longer.

🇺🇸

Susan

10

January 2024

The staff and owner are incredibly welcoming and friendly. They make sure your every want and need are met. The rooms are beautifully decorated with high quality linens and pleasant special touches like fireplaces, electric candles and small refrigerators. The breakfast is amazing too. It’s a wonderful retreat spot that is very quiet yet also reasonably close to the beach and the local shops and restaurants. We had such a lovely stay. Can’t wait to come back!

🇦🇺

Joachim

10

November 2023

The Homestead is a high quality B & B with very accommodating hosts. The rooms are very comfortable and all have record players which was fun to play a few a few old albums. The interior design and furnishings made for a very homely and relaxing atmosphere. The breakfast was very nice after our morning walk to the beach. It’s a shame our stay was so brief, 2 or 3 nights would have been ideal. Thanks Ray and Susanna for your welcome and hospitality.

🇩🇪

Katrin

10

August 2023

Everything Once there, we immediately felt at home. We were very warmly welcomed, we were shown the house and our room. There was a handwritten card waiting for us, with which we were once again welcomed. I can not even write down all the little attentions. We were cared for the whole stay. We were really sad when our stay was over. This accommodation alone is worth another trip to the USA. I hope this is not the last time we have been there.

Having to leave

🇺🇸

Murone

10

August 2023

The room was well equipped and comfortable. They thought of every detail to make our stay comfortable. The breakfasts were great and lots of snacks available. For us it was also a perfect location.

The bed in room 7 wasn't all that comfortable and it was noisy, everytime my husband moved it woke me up. We booed through booking.com and my gluten-free instructions didn't get passed on to the staff. Book directly for the best stay.

Points of Interest Around The Homestead

Airports

Tweed-New Haven Airport

14mi

Long Island Mac Arthur Airport

42.2mi

Bradley International Airport

45.7mi

Westchester County Airport

58.7mi

Amenities of The Homestead

Free Private Parking

Free wifi

Streaming service (like Netflix)

Air conditioning

Sun deck

Private entrance

Parking On Site

Terrace

Non-smoking rooms

Beach umbrellas

Beach chairs/Loungers

Patio

Picnic area

Garden

Free toiletries

View

Bidet

Bathtub

Stay rules - The Homestead

  • Check-in / Check-out

  • Pets

  • Internet

  • Age restrictions

  • Curfew

  • Parking

  • Reservations

  • Children and beds

  • Cards accepted at this property