Book Madison Bed & Breakfast

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

B&B in Madison

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (237)
"Everything was fantastic, will stay again!"
$197 nightly
The price is $219
Sep 3 - Sep 4
Total includes taxes and fees
The Captain Stannard

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (82)
"Best breakfast. The little things that were provided (warm bathroom towels, comfortable bed, patio outside our room just for us to enjoy) added to our wonderful 3 day get away in Madison. Don't want to forget the freshly made popcorn in the evening we so enjoyed. "
The Homestead

Jay's Ranch

4.0 star property
7.6 out of 10, Good, (44)
"This was an amazing stay. Renee is a great host. She is clean, personable, and professional. The home is very cozy, and while still a work in progress, the outdoor area is beautiful and teeming with potential. This is not a hotel or a motel, understanding this, do not expect the starchy atmosphere of those places, but instead appreciate the friendly, homely vibe. If you’re looking for somewhere reasonably priced, clean, and cozy, this is a great spot."
$109 nightly
The price is $125
Aug 6 - Aug 7
Total includes taxes and fees
Jay's Ranch

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (7)
"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. "
Vine & Sand

The Bevin House Bed & Breakfast

3.5 star property
9.6 out of 10, Exceptional, (77)
"Welcoming, fun, and absolutely stunning! A cuddly turkey didn’t hurt either. "
$260 nightly
The price is $289
Aug 17 - Aug 18
Total includes taxes and fees
The Bevin House Bed & Breakfast

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very Good, (33)
"Very convenient location next to Cresent Beach and Leon 1909 restaurant which is fantastic! "
$314 nightly
The price is $358
Aug 21 - Aug 22
Total includes taxes and fees
West Neck Guesthouse

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (23)
"Very comfortable king size bed. Excellent gourmet breakfast, discreet host. Older house, but all the comforts. Absolutely every need provided for. "
Stirling House Bed & Breakfast

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (155)
"My granddaughter and I had a lovely stay."
$187 nightly
The price is $208
Sep 3 - Sep 4
Total includes taxes and fees
Westbrook Inn B&B

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
James Pharmacy Bed & Breakfast

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (13)
"very comfortable stay. "
The Farmhouse Bed and Breakfast

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (10)
"Beautiful bed and breakfast with gorgeous views. Close to shops and restaurants but far enough to be private and quiet. Will definitely be coming back"
Harbor Knoll Bed & Breakfast

Higganum House B&B

3.0 star property
Higganum House B&B

Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

$863 nightly
The price is $976
Aug 6 - Aug 7
Total includes taxes and fees
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

Thimble Islands Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (4)
"A beautiful, quiet home in a stunning setting run by two extremely gracious hosts. Breakfast on both days was excellent."
Thimble Islands Bed & Breakfast

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (15)
"Two mid age couples just had a good and relaxing time with great hospitality. "
Arbor View House B&B

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

10.0 out of 10, Exceptional, (1)
"Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great...
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

SEVEN - Shelter Island Guest House

2.5 star property
9.8 out of 10, Exceptional, (57)
"It was a beautiful place! Under construction however, Beth was Amazing! Amelia was so hospitable. Close to everything and it certainly helped that the weather was spectacular! Will definitely go back another time!"
SEVEN - Shelter Island Guest House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Madison Hotel Reviews

Frequently asked questions

What are the most popular Madison B&Bs?
The Homestead stands out as an exceptional choice for travelers seeking a cozy retreat in Madison, boasting a superb 10.0 rating. This charming bed and breakfast is renowned for its attentive service and friendly setting, making it ideal for couples desiring a romantic getaway or solo travelers looking to unwind. Guests rave about the owner and staff, who pay meticulous attention to every detail, ensuring a stress-free stay. The inviting patio and terrace are superb for enjoying morning coffee or relaxing in the evening sun.

For those who appreciate a hearty breakfast, The Scranton Seahorse Inn is a delightful option with an excellent 9.2 rating. This property offers complimentary full breakfasts that are a highlight for many guests, with favorites like delicious omelettes that cater to various tastes. The historical charm of the inn adds a unique touch to your stay, making it a great pick for families or groups looking to explore the area together. The patio and terrace provide lovely outdoor spaces for family gatherings or quiet moments away from the hustle and bustle.
What is the nightly rate for a B&B in Madison?
Prices for B&Bs in Madison often vary, but you can find a great deal from $125 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Madison B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
Are there any family-friendly Bed and Breakfasts in Madison?
The Homestead is a wonderful choice for families visiting Madison. This charming B&B features connecting rooms, making it easy for parents to keep an eye on their little ones while enjoying some privacy. The inviting garden provides a superb space for kids to play and explore, while the on-site snack bar ensures that everyone can grab a quick bite when hunger strikes.

Another excellent option is The Scranton Seahorse Inn, which is particularly accommodating for families. With cozy rooms that include a convenient sofa bed, there's ample space for everyone to rest comfortably after a day of adventures. Daily housekeeping adds to the convenience, ensuring that your family can focus on making memories rather than managing chores. The beautifully maintained garden is a lovely spot for children to enjoy the outdoors while parents relax nearby.
Do any Madison Bed & Breakfasts allow dogs?
The Homestead in Madison, CT, is a delightful choice for dog owners looking for a welcoming retreat. This charming property not only allows dogs but also ensures a pet-friendly environment with amenities like a private yard and patio where your furry friends can roam freely. Guests can enjoy complimentary continental breakfasts, cozy up by the fireplace, and unwind in rooms adorned with premium bedding and Egyptian cotton sheets, making it a comfortable stay for the entire family.

Another fantastic option is The Scranton Seahorse Inn, which also permits pets and provides thoughtful touches such as food and water bowls for your four-legged companions. This inn features a lovely patio and terrace, superb for relaxing after a day of adventures. With a full breakfast included, guests can savor a hearty meal to kickstart their day, while the private hot tub offers a soothing retreat for adults in the evening. The combination of attentive service and family-friendly amenities makes this property a great fit for travelers seeking both comfort and convenience while enjoying a laid-back getaway with their pets.
Which area is best to stay in a Madison B&B?
Madison Center is the top choice for travelers seeking a B&B experience in Madison. This vibrant area offers a charming coastal atmosphere with easy access to local shops and restaurants. Families will appreciate the nearby Hammonasset Beach State Park, where children can enjoy sandy shores and safe swimming. The park also features picnic areas, making it an ideal spot for a family outing.

For those interested in culture, Madison Center is close to the Madison Historical Society, which provides insights into the town's rich history. Nature lovers can explore the scenic trails at the nearby Madison Land Conservation Trust, great for walking and birdwatching.

Couples seeking a romantic escape will find the quaint streets of Madison Center lined with unique boutiques and cafes, ideal for leisurely strolls together. The area's inviting ambiance, combined with attentive service from local B&Bs, ensures a memorable stay filled with comfort and convenience.
When is the best time to book a Bed & Breakfast in Madison?
The best time to book a B&B in Madison is during the vibrant summer months, particularly in July. This is when the city comes alive with a variety of outdoor festivals, cultural events, and a bustling atmosphere that appeals to visitors seeking both relaxation and adventure. With warm temperatures ranging from the mid-60s to the low 80s Fahrenheit, July provides ideal conditions for sightseeing, strolling along the picturesque lakes, and exploring the charming downtown area.

During the peak season from June to August, you can immerse yourself in Madison's dynamic arts scene, enjoy food festivals, and even take part in water activities on the beautiful lakes that surround the city. The lively ambiance is complemented by a rich array of local dining options, making it a great time for food enthusiasts.

If you're looking for a more budget-friendly experience, consider visiting in December. While this month is part of the low season, it offers a unique charm, particularly with the festive holiday decorations and events that create a cozy atmosphere. You can enjoy a quieter pace while still experiencing the warmth of local hospitality.
What is the difference between a Madison B&B and a hotel?
Every Madison B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Madison B&Bs.