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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
Lobby sitting area
Exterior
36-inch Smart TV with cable channels, TV, Netflix
Bicycling

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pet-friendly
  • Parking included
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View in a map
391 Boston Post Rd, Madison, CT, 06443
  • Place, beach near Parker Avenue
    ‪2 min drive‬
  • Place, beach near Madison Center
    ‪2 min drive‬
  • Place, RJ Julia Booksellers
    ‪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 duvets, memory-foam beds

Room, 1 King Bed, Ground Floor (1)

10.0 out of 10
Exceptional
(2 reviews)
  • 20 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

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 duvets, memory-foam beds

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

  • 29 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

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

Room, 2 Queen Beds, Ground Floor (4) | Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

Room, 2 Queen Beds, Ground Floor (4)

10.0 out of 10
Exceptional
(1 review)
  • 22 sq m
  • Sleeps 4
  • 2 Queen Beds
  • Free Wi-Fi

View all photos for Room, 1 King Bed, Fireplace

Room, 1 King Bed, Fireplace | Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

Room, 1 King Bed, Fireplace

  • 25 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

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

Room, 1 King Bed, Ground Floor (5) | Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

Room, 1 King Bed, Ground Floor (5)

10.0 out of 10
Exceptional
(2 reviews)
  • 19 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

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

Room, 1 King Bed (11) | Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

Room, 1 King Bed (11)

9.2 out of 10
Wonderful
(5 reviews)
  • Garden view
  • 20 sq m
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

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

Room, 1 King Bed, Patio, Ground Floor (6) | Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

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

  • 20 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

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 duvets, memory-foam beds

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

  • 24 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

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

Room, 2 Queen Beds, Fireplace (14) | Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

Room, 2 Queen Beds, Fireplace (14)

  • 23 sq m
  • 1 bedroom
  • Sleeps 2
  • 2 Queen Beds
  • Free Wi-Fi

View all photos for Room, Fireplace (12)

Room, Fireplace (12) | Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

Room, Fireplace (12)

10.0 out of 10
Exceptional
(1 review)
  • 19 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed
  • Free Wi-Fi

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

Superior Room, 2 Bedrooms, Bathtub, Garden View | Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

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 Wi-Fi

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About this property

The Homestead

Along with a snack bar/deli, this smoke-free bed & breakfast has free use of bicycles and express check-out. Free continental breakfast, free WiFi in public areas and free self parking are also provided. Additionally, wedding services, a garden and a fireplace at reception are on-site. Housekeeping is available on request.
The Homestead offers 10 air-conditioned accommodations with complimentary bottles of water and a hairdryer. Each accommodation is individually furnished and decorated. Memory foam beds feature Egyptian cotton sheets, down duvets and premium bedding. 36-inch Smart televisions come with premium cable channels and Netflix.

Bathrooms include a shower. This Madison bed & breakfast provides complimentary wireless Internet access. Hypo-allergenic bedding, an iron/ironing board and change of towels can be requested. Housekeeping is provided 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.

Our customers tell us that they can't get enough of the helpful staff at The Homestead. During your stay, you'll be within walking distance of Madison Green Historic District. Enjoy features like free breakfast, free WiFi in public areas and free self-parking.
  • Free continental breakfast served daily
  • Free WiFi
  • Free self-parking
  • Amenities include a car charging station, multilingual staff and a terrace
  • On-site recreation includes complimentary bicycles
  • Just a 5-minute drive from Hammonasset Beach State Park and 8 minutes from Clinton Crossing Premium Outlets
  • Dogs welcome for a fee (restrictions apply)
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.

Guests are served a free continental breakfast daily from 8:00 AM to 10:00 AM.

Property amenities

Internet

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

Parking and transport

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

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
  • Smoke-free property
  • 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
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 25 per accommodation, per night
  • Only dogs are allowed
  • Maximum 1 (weight limit: 30 lb per pet)
  • Certain rooms only
  • 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.
  • Cots (infant beds) are not available.

Payment types at the property

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 25 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

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
This property does not have a front desk. To arrange for check-in, guests must contact the property at least 24 hours prior to arrival using the information on the booking confirmation. Guests arriving after 8:00 PM must make advance arrangements by contacting the property using the information on the booking confirmation. Guests must contact the property in advance for check-in instructions. The host will greet guests on arrival.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

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 specific rooms only, which can be requested by contacting the property directly at the number on your booking confirmation (please see the Fees section for related charges).

Property is also known as

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

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

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

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

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

Stephanie

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

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

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

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

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

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

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

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 traveller

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

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

Tamara

Liked: Cleanliness, amenities, property conditions & facilities
So charming! The Inn itself is nicely furnished in a cozy manner, curated with interesting collections of things and vintage or antique objects throughout. Many charming touches, like the popcorn station with flavored oils and Parmesan cheese, were a delightful surprise. The towel warmer in the bathroom was unexpected and wonderful! We had to rush out In the morning, but not before we grabbed, homemade zucchini bread, coffee, and sausage& egg bites for the road. Overall, a warm, friendly, and lovely place to stay.
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

Verified traveller

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

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

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

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