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The Homestead

3.0 star property

Choose dates to view prices

Photo gallery for The Homestead

Room, 1 King Bed, Patio, Ground Floor (2) | Terrace/patio
Exterior
Bicycling
36-inch Smart TV with cable channels, TV, Netflix
Lobby sitting area

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, beach near Flower Avenue
    ‪2 min drive‬
  • Place, beach near Madison Center
    ‪2 min drive‬
  • Place, Scranton Memorial Library
    ‪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)

Room, 1 King Bed, Ground Floor (1) | Egyptian cotton sheets, premium bedding, down comforters

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)

Room, 1 King Bed, Patio, Ground Floor (2) | Egyptian cotton sheets, premium bedding, down comforters

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
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

View all photos for Room, 1 King Bed, Fireplace

Room, 1 King Bed, Fireplace | Egyptian cotton sheets, premium bedding, down comforters

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)

Room, 1 King Bed, Ground Floor (5) | Egyptian cotton sheets, premium bedding, down comforters

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
  • 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)

Room, 1 King Bed, Patio, Ground Floor (7) | Egyptian cotton sheets, premium bedding, down comforters

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)

Room, 2 Queen Beds, Fireplace (14) | Egyptian cotton sheets, premium bedding, down comforters

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

Located in Madison Center, The Homestead is 2.5 mi (4.1 km) from Hammonasset Beach State Park and within a 10-minute drive of other popular attractions like Clinton Crossing Premium Outlets. This 3-star bed & breakfast has 10 rooms and welcomes guests with free breakfast, a private beach, and free in-room WiFi.
View more B&B in MadisonOpens in a new window

What's nearby

  • beach near Flower Avenue - 2 min drive - 0.9 miles
  • beach near Parker Avenue - 2 min drive - 0.9 miles
  • beach near Madison Center - 2 min drive - 1.1 miles
  • Scranton Memorial Library - 2 min drive - 1.6 miles
  • RJ Julia Booksellers - 2 min drive - 1.6 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
  • ‪Starbucks - ‬8 min drive
  • ‪Cumberland Farms - ‬3 min drive
  • ‪Starbucks - ‬3 min drive

About this property

The Homestead

Guests of The Homestead enjoy free WiFi in public areas, free use of bicycles, and express check-out. If you decide to drive, there's free parking. Multilingual staff is on hand to answer questions. Other amenities at this beach bed & breakfast include a terrace, a fireplace in the lobby, and wedding services.
36-inch Smart TVs come with cable channels and Netflix, and guests can stay connected with free WiFi. Bathrooms offer hair dryers, and memory foam beds with Egyptian cotton sheets and down comforters ensure a restful night. Wardrobes or closets are also included. Housekeeping is available on request.
Recreational amenities at the bed & breakfast include complimentary bicycles.

The recreational activities listed below are available either on site or nearby; fees may apply.

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Jul 12 - Jul 13
Total with taxes and fees
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Property amenities

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

Family friendly

  • Snack bar/deli

Conveniences

  • Hair salon
  • Water dispenser

Guest services

  • Change of bedsheets (on request)
  • Change of towels on request
  • Housekeeping (on request)
  • Multilingual staff
  • Wedding services

Outdoors

  • Firepit
  • Garden
  • Outdoor furniture
  • Terrace

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

More

  • Fireplace in lobby
  • Smoking not allowed
  • Water dispenser usage encouraged

Room amenities

Bedroom

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

Bathroom

  • Hair dryer
  • Private bathroom
  • Shower
  • Towels provided

Entertainment

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

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

  • This property welcomes pets for USD 60 per accommodation, per night
  • Dogs only
  • 1 total (35 lbs is the maximum weight per pet)
  • Pets may not be left unsupervised
  • Certain rooms only, restrictions apply
  • Guests can request a pet-friendly room by contacting the property at the number on the booking confirmation
  • Service animals exempt from fees

Property payment types

Important information

Optional extras

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

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

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

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
  • Check-in: 3:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 21
Driving? This property offers free parking, along with a car charging station.

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • This property accepts credit cards. Cash is not accepted. 
  • The credit card used at check-in for incidentals must be in the name of the primary guest who made the reservation.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit.
  • Cashless payment methods are available for all transactions.

Additional information about polices, regulations, and more:

  • Connecting or adjoining rooms can be requested, but all rooms are subject to availability. Contact the property using the phone number on your booking confirmation.
  • There are no elevators.
  • No cribs or infant beds are available.
  • No rollaway or extra beds are available.
  • Noise-free rooms can't be guaranteed.

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

Is a free cancellation option available at The Homestead?

The Homestead provides free cancellation on certain room rates. To learn more, review the cancellation policy on Orbitz.

How much does it cost to stay at The Homestead?

As of Jul 3, 2026, prices found for a 1-night stay for 2 adults at The Homestead on Jul 19, 2026 start from $376, 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.

What is there to do around The Homestead?

This bed & breakfast is situated in Madison Center within a short 16-minute walk of Madison Green Historic District. You'll also find Hammonasset Beach State Park and Guilford Town Green within a short drive.

Is parking available on site at The Homestead?

Yes, self parking is offered for free at the bed & breakfast. An electric car charging station and bicycle parking are also available.

Does The Homestead include a casino at the property?

No, The Homestead doesn't have a casino.

Is there an indoor pool at The Homestead?

No, there is no indoor pool at this bed & breakfast.

Is The Homestead a good place to stay for couples?

Couples staying at this bed & breakfast will appreciate amenities like Egyptian cotton sheets and Netflix as well as wedding services.

Are there hot tubs at The Homestead?

No, this bed & breakfast doesn't have a spa tub.

Does The Homestead have a restaurant that serves breakfast?

Yes, The Homestead serves free continental breakfast each morning from its snack bar.

Will The Homestead allow pets to stay for free?

Although they can't stay for free, dogs are welcome at The Homestead for a fee of USD 60 per accommodation, per night.

Are there connecting rooms at The Homestead?

Yes, this bed & breakfast has connecting rooms you can book for your group event or vacation.

How far is the airport from The Homestead?

The closest major airport to The Homestead is New Haven, CT (HVN-Tweed - New Haven Regional), which is 15.9 mi away (22 minutes by car). Another top airport is Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), which is around 28 mi away.

Are there rooms with balconies that I can book at The Homestead?

Yes, some guestrooms at this bed & breakfast offer either a balcony/patio and a deck/patio where guests can enjoy garden views.

Does The Homestead offer wedding services?

If you plan to exchange vows during your trip, consider the wedding services available at The Homestead.

The Homestead Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 88 out of 92 reviews
Rating 8 - Good. 3 out of 92 reviews
Rating 6 - Okay. 1 out of 92 reviews
Rating 4 - Poor. 0 out of 92 reviews
Rating 2 - Terrible. 0 out of 92 reviews

10/10

Cleanliness

10/10

Staff & service

9.8/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified

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

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

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

10/10 Excellent

Ken

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

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

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

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

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

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

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

10/10 Excellent

Stephanie

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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