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The Homestead

3.0 star property
3-star beach B&B near Hammonasset Beach State Park

Choose dates to view prices

Photo gallery for The Homestead

Room, 1 King Bed, Patio, Ground Floor (2) | Terrace/patio
A living room with a fireplace, a television mounted above it, and two armchairs.
A cozy kitchen with a coffee machine, a fruit bowl, and a 'NO SELF-SERVICE' sign.
A two-story white house with black shutters, a covered porch, and a red umbrella.
A teal bicycle with a wicker basket parked in front of a white building with green shutters.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
391 Boston Post Rd, Madison, CT, 06443
  • Place, Madison Green Historic District
    ‪18 min walk‬
  • Place, Deacon John Grave House
    ‪2 min drive‬
  • Place, beach near Madison Center
    ‪2 min drive‬
  • Airport, New Haven, CT (HVN-Tweed - New Haven Regional)
    ‪26 min drive‬

Room options

View all photos for Room, 1 King Bed, Ground Floor (1)

A bedroom with a bed, a chair, a TV, a wardrobe, and a painting on the wall.

Room, 1 King Bed, Ground Floor (1)

10.0 out of 10
Exceptional
(2 reviews)
  • 212 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Room, 1 King Bed, Patio, Ground Floor (2)

A bedroom with a bed, a dresser, a vanity, and a chandelier.

Room, 1 King Bed, Patio, Ground Floor (2)

  • 317 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Room, 2 Queen Beds, Ground Floor (4)

A hotel room with two beds, a white headboard, a wooden floor, and artwork on the walls.

Room, 2 Queen Beds, Ground Floor (4)

10.0 out of 10
Exceptional
(1 review)
  • 236 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

View all photos for Room, 1 King Bed, Fireplace

A neatly made bed with white linens in a hotel room.

Room, 1 King Bed, Fireplace

  • 266 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Room, 1 King Bed, Ground Floor (5)

A bedroom with a large bed, a television on a stand, a dresser, and a window with blinds.

Room, 1 King Bed, Ground Floor (5)

10.0 out of 10
Exceptional
(2 reviews)
  • 205 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Room, 1 King Bed (11)

A bedroom with a large bed, a dresser, a desk, a television, and a mirror.

Room, 1 King Bed (11)

9.2 out of 10
Wonderful
(5 reviews)
  • Garden view
  • 215 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Room, 1 King Bed, Patio, Ground Floor (6)

A bedroom with a bed, dresser, and a television on a stand.

Room, 1 King Bed, Patio, Ground Floor (6)

  • 215 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Room, 1 King Bed, Patio, Ground Floor (7)

A bedroom with a bed, a chair, a fireplace, and a television.

Room, 1 King Bed, Patio, Ground Floor (7)

  • 257 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Room, 2 Queen Beds, Fireplace (14)

A hotel room with two beds, a large abstract painting, a window with blinds, and a tall floor lamp.

Room, 2 Queen Beds, Fireplace (14)

  • 245 sq ft
  • 1 bedroom
  • Sleeps 2
  • 2 Queen Beds
  • Free WiFi

View all photos for Room, Fireplace (12)

A bedroom with a wooden bed, a white bedside table, a mirror, a white sink, and a cowhide rug.

Room, Fireplace (12)

10.0 out of 10
Exceptional
(1 review)
  • 205 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed
  • Free WiFi

View all photos for Superior Room, 2 Bedrooms, Bathtub, Garden View

A bedroom with a teal upholstered bed, a patterned blue carpet, a television on a stand, and a fireplace.

Superior Room, 2 Bedrooms, Bathtub, Garden View

10.0 out of 10
Exceptional
(1 review)
  • Garden view
  • 1 bedroom
  • Sleeps 7
  • 1 King Bed and 2 Double Beds
  • Free WiFi

About the neighborhood

Madison

Madison Center stay.A stay at this Madison Center B&B places you within 3 miles (5 km) of Hammonasset Beach State Park and 6 miles (10 km) of Hammonasset Beach. Clinton Crossing Premium Outlets is within 6 miles (10 km) and Chamard Vineyards is within 9 miles (15 km).
View more B&B in MadisonOpens in a new window

What's nearby

  • Madison Green Historic District - 18 min walk - 1.0 mile
  • Deacon John Grave House - 2 min drive - 1.4 miles
  • beach near Madison Green Historic District - 2 min drive - 0.9 miles
  • beach near Flower Avenue - 2 min drive - 0.9 miles
  • beach near Madison Center - 2 min drive - 1.1 miles

Getting around

  • Madison Station - 6 min drive
  • New Haven, CT (HVN-Tweed - New Haven Regional) - 22 min drive

Restaurants

  • ‪McDonald's - ‬8 min drive
  • ‪Dunkin' - ‬8 min drive
  • ‪Cumberland Farms - ‬3 min drive
  • ‪Starbucks - ‬3 min drive
  • ‪Starbucks - ‬8 min drive

About this property

The Homestead

3-star beach B&B near Hammonasset Beach State Park
A private beach is featured. There's a snack bar/deli on site. Free breakfast is available daily. WiFi is free in public spaces.

A terrace, multilingual staff, and a garden are also featured at The Homestead. Self parking is free.

This 3-star Madison bed & breakfast is smoke free.

  • 10 guestrooms or units
  • Continental breakfast (free)
  • Deli
  • Charging station for electric cars
  • Express check-out
  • Staff is multilingual
  • Wedding services available
  • Terrace
  • Garden
  • Beauty salon
  • Fireplace in lobby
  • Television in lobby
  • No smoking on site
  • Water dispenser
The Homestead offers 10 air-conditioned accommodations with complimentary bottled water and hair dryers. Each accommodation is individually furnished and decorated. Memory foam beds feature Egyptian cotton sheets, down comforters, and premium bedding. 36-inch Smart televisions come with premium cable channels and Netflix.

Bathrooms include showers. This Madison bed & breakfast provides complimentary wireless Internet access. Hypo-allergenic bedding, irons/ironing boards, and change of towels can be requested. Housekeeping is provided on request.

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  • Pet friendly
  • Parking included
  • Free WiFi
4.5 out of 5, Wonderful, 174 reviews
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The price is $122
Aug 30 - Aug 31
Total with taxes and fees
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Property amenities

Family friendly

  • Snack bar/deli

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • Electric car charging station on site
  • Free self parking on site

Food and drink

  • Free continental breakfast available daily 8:00 AM to 10:00 AM
  • Snack bar/deli

Things to do

  • Bicycle storage
  • Free bicycle rentals
  • TV in common areas
  • Wine tours

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Grab bar in shower
  • Hand-held showerhead
  • Handrails in stairways
  • Height-adjustable showerhead
  • Upper floors accessible by stairs only
  • Well-lit path to entrance

Room amenities

Entertainment

  • 36-inch smart TV with premium cable channels
  • Netflix
  • Streaming services

Bedroom

  • Down comforter
  • Egyptian cotton sheets
  • Hypo-allergenic bedding
  • Memory foam mattress

Bathroom

  • Hair dryer
  • Private bathroom
  • Shower
  • Towels provided

Food and drink

  • Free bottled water

More

  • Air conditioning
  • Connecting rooms available
  • Electrical adapters
  • Heating
  • Individual decor
  • Individual furnishings
  • Iron/ironing board on request
  • Window screens

Policies

Check-in

Check-in start time: 3:00 PM; Check-in end time: 8:00 PM
Late check-in subject to availability
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM
Contactless check-out available
Express check-out available

Special check-in instructions

There is no front desk at this property
Guests must contact the property in advance for check-in instructions; your host will greet you
To make arrangements for check-in please contact the property at least 24 hours before arrival using the information on the booking confirmation
If you are planning to arrive after 8:00 PM please contact the property in advance using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools

Access methods

Host will greet you

Pets

  • Pets: USD 60 per accommodation, per night
  • Only dogs are allowed
  • Maximum 1 (weight limit: 35 lbs per pet)
  • Pets cannot be left unattended
  • Certain rooms only, restrictions apply
  • You can request a pet-friendly room by reaching out to the property at the number on the booking confirmation
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.
  • Cribs (infant beds) are not available.

Property payment types

Important information

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • Pet fee: USD 60 per accommodation, per night
  • Service animals are exempt from fees

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
The name on the credit card used at check-in to pay for incidentals must be the primary name on the guestroom reservation
This property accepts credit cards; cash is not accepted
Cashless transactions are available
Noise-free guestrooms cannot be guaranteed
Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. The name on the credit card used at check-in to pay for incidentals must be the primary name on the guestroom reservation. This property accepts Visa, Mastercard, American Express, and Discover. Cash is not accepted. Noise-free guestrooms cannot be guaranteed.
    For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation. Cashless payment methods are available for all transactions.

We should mention

  • Connecting/adjoining rooms are subject to availability and can be requested by contacting the property at the number on your booking confirmation.
  • Pets are welcome in certain rooms only; other restrictions apply (please see the Fees section for related charges). To make arrangements for your pet, contact the property directly at the number on your booking confirmation.

Property is also known as

Homestead B&B Madison
Homestead Madison
The Homestead Madison
The Homestead Bed & breakfast
The Homestead Bed & breakfast Madison

Frequently asked questions

How close is The Homestead to the airport?

The Homestead is 15.9 mi (22-min drive) away from the New Haven, CT (HVN-Tweed - New Haven Regional) airport, the closest popular airport to the property.

How much does it cost to stay at The Homestead?

As of Aug 2, 2026, prices found for a 1-night stay for 2 adults at The Homestead on Aug 6, 2026 start from $365, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Does The Homestead have an airport shuttle?

Airport shuttle services are not available at The Homestead.

How close is The Homestead to the beach?

This bed & breakfast is 4 mi (10-min drive) from Hammonasset Beach and 8.7 mi (18-min drive) from Clinton Town Beach. Don't forget your sunscreen!

Does The Homestead offer free breakfast?

The Homestead offers free continental breakfast every day from 8:00 AM to 10:00 AM.

Is there a casino at The Homestead?

No, there is no casino at this bed & breakfast.

What time is check-in at The Homestead?

Check-in start time: 3:00 PM; Check-in end time: 8:00 PM.

Is there free parking at The Homestead?

This bed & breakfast offers free self parking.

Does The Homestead have a pool?

The Homestead does not have a pool.

Does The Homestead have a spa?

There are no spa services available at this bed & breakfast.

How close is The Homestead to downtown Madison?

The Homestead is 2.4 mi away from Madison.

The Homestead Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 93 out of 97 reviews
Rating 8 - Good. 3 out of 97 reviews
Rating 6 - Okay. 1 out of 97 reviews
Rating 4 - Poor. 0 out of 97 reviews
Rating 2 - Terrible. 0 out of 97 reviews

10/10

Cleanliness

10/10

Staff & service

9.8/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Anthony

Liked: Cleanliness, amenities, property conditions & facilities
Beautiful property- wonderful staff- clean, comfortable and relaxed feeling with a lovely breakfast 😄
Stayed 1 night in Dec 2025
Verified review

10/10 Excellent

Cynthia

Liked: Cleanliness, staff & service, property conditions & facilities
This is our 2nd year staying at the Homestead B & B. We absolutely love it here! Great food, amenities galore, and just an awesome getaway!
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Carolyn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful rooms, exceptional staff, and convenient location
Stayed 5 nights in Dec 2024
Verified review

10/10 Excellent

Ken

Liked: Cleanliness, staff & service, property conditions & facilities
Excellent accommodations and Host.
Stayed 1 night in Oct 2023
Verified review

10/10 Excellent

Gustavo

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Best Bed & Breakfast in the area
Stayed 2 nights in Apr 2023
Verified review

10/10 Excellent

Gregory

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful and comfortable b+b. Well thought out amenities such as comfortable bed, fluffy towels, great breakfast options and snacks. The innkeepers friendly and made sure we were well taken care of during our stay
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

Stephen

Liked: Cleanliness, property conditions & facilities, room comfort
My wife and I had wonderful stay at The Homestead! Brit our host was just so nice and accomadating. The room was beautiful and very clean. Breakfast was excellent each and every day!
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Bindi

Liked: Cleanliness, staff & service, property conditions & facilities
Amazing place! Loved the stay! Super friendly staff and we got to meet the owner wuo is super cool!
Stayed 4 nights in May 2023
Verified review

10/10 Excellent

Stephanie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff extremely friendly and welcoming.
Stayed 5 nights in Apr 2023
Verified review

10/10 Excellent

Allison

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was perfect! Innkeepers were so friendly and helpful. We loved the vinyl records and breakfast was delicious! Seriously, every detail was considered by the staff! We would love to stay here again!
Stayed 1 night in Aug 2025
Verified review

10/10 Excellent

Karen

Liked: Cleanliness, amenities, property conditions & facilities
We had an absolutely fabulous stay at The Homestead. Everything about it is wonderful…. From the location to the beautiful room and breakfast area, but what stood out the most was our lovely friendly host Brit!! Lovely breakfasts, great tips on the area and great to chat to. Attention to detail at the Homestead is spot on. Thank you for everything!!!
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

kenneth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Amazingly clean and nice room. Would definitely stay again
Stayed 1 night in Sep 2022
Verified review

10/10 Excellent

Cicek

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great property, cosy, homey, nicely furnished, with lots of interesting gadgets, nick nacks. Great breakfast. Friendly host and staff. This was our 3rd time, will definitely go there again.
Stayed 1 night in Jan 2025
Verified review

10/10 Excellent

Mark

Liked: Cleanliness, staff & service, property conditions & facilities
This is a very charming B&B. Staff and owners were great. Very friendly and accommodating. Rooms were clean and well appointed; very clean; nice firm beds and selection of pillows. Will definitely stay again.
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Best Place to Stay in Madison!!!!!

Amazing place to stay! Clean, beautiful, very friendly staff…especially Heartman❤️! Highly recommend!!!!!!!!!!!
Stayed 2 nights in Jul 2022
Verified review

10/10 Excellent

John

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

love New England

Great area , Great people,
Stayed 4 nights in Nov 2024
Verified review

10/10 Excellent

John

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Happy

Great people and accommodations
Stayed 2 nights in Nov 2024
Verified review

10/10 Excellent

Daphne

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Charming in every aspect. Highly recommend, Hosts are wonderful people.
Stayed 1 night in Feb 2025
Verified review

10/10 Excellent

Gary

Liked: Cleanliness, staff & service, property conditions & facilities
We really enjoyed the Homestead. Milford is a fantastic coastal town. Beautiful homes, nice beaches and quiet. If we come back to this area we will stay at the Homestead.
Stayed 1 night in May 2023
Verified review

10/10 Excellent

Laura

Liked: Cleanliness, staff & service, property conditions & facilities
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.
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

David

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great CT getaway.

A wonderful experience. I would highly recommend this place to anyone looking for a comfortable, relaxing and friendly place to stay.
Stayed 1 night in Oct 2022
Verified review

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Wonderful, convenient, friendly, thoughtful touches and accessories.
Stayed 2 nights in Jan 2025
Verified review

10/10 Excellent

Marc

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Such an adorable place! So homey. Staff was very attentive to all needs.
Stayed 2 nights in Aug 2022
Verified review

10/10 Excellent

Doreen

Liked: Cleanliness, staff & service, property conditions & facilities
The place is beautiful and very well appointed. Everyone was friendly and professional. The only issue was that the room was very warm and there was no thermostat in the room to adjust the temp.
Stayed 1 night in Nov 2025
Verified review

10/10 Excellent

Donald

Liked: Cleanliness, property conditions & facilities
A very large property with ample parking. Beautiful sitting areas and well maintained yard.
Stayed 1 night in May 2023

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