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The Homestead

3.0 star property
Beach bed & breakfast with a nearby private beach and free breakfast

Choose dates to view prices

Photo gallery for The Homestead

Room, 1 King Bed, Patio, Ground Floor (7) | Egyptian cotton sheets, premium bedding, down comforters
Exterior
36-inch Smart TV with cable channels, TV, Netflix
Exterior
Traditional House | Living area | 36-inch Smart TV with cable channels, TV, Netflix

Reviews

10 out of 10
Exceptional

Popular amenities

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

Explore the area

View in a map
391 Boston Post Rd, Madison, CT, 06443
  • Place, Hammonasset Beach State Park
    ‪5 min drive‬
  • Place, Clinton Crossing Premium Outlets
    ‪9 min drive‬
  • Place, Hammonasset Beach
    ‪10 min drive‬
  • Airport, New Haven, CT (HVN-Tweed - New Haven Regional)
    ‪23 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
  • Sleeps 2
  • 1 King Bed

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
  • Sleeps 2
  • 1 King Bed

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

Room, 2 Queen Beds, Ground Floor (4) | Egyptian cotton sheets, premium bedding, down comforters

Room, 2 Queen Beds, Ground Floor (4)

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

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
  • Sleeps 2
  • 1 King Bed

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
  • Sleeps 2
  • 1 King Bed

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

Room, 1 King Bed (11) | Egyptian cotton sheets, premium bedding, down comforters

Room, 1 King Bed (11)

9.2 out of 10
Wonderful
(5 reviews)
  • 215 sq ft
  • Sleeps 2
  • 1 King Bed

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 comforters

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

  • 215 sq ft
  • Sleeps 2
  • 1 King Bed

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
  • Sleeps 2
  • 1 King Bed

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
  • Sleeps 2
  • 2 Queen Beds

View all photos for Room, Fireplace (12)

Room, Fireplace (12) | Egyptian cotton sheets, premium bedding, down comforters

Room, Fireplace (12)

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

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

Superior Room, 2 Bedrooms, Bathtub, Garden View | Egyptian cotton sheets, premium bedding, down comforters

Superior Room, 2 Bedrooms, Bathtub, Garden View

10.0 out of 10
Exceptional
(1 review)
  • Sleeps 7
  • 1 King Bed and 2 Double Beds

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

  • Hammonasset Beach State Park - 5 min drive - 2.7 miles
  • Clinton Crossing Premium Outlets - 9 min drive - 6.6 miles
  • Hammonasset Beach - 10 min drive - 4.6 miles
  • Clinton Town Beach - 12 min drive - 6.6 miles
  • Stony Creek - Thimble Islands Historic District - 13 min drive - 8.6 miles

Getting around

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

Restaurants

  • ‪Cumberland Farms - ‬3 min drive
  • ‪Starbucks - ‬3 min drive
  • ‪Bradley & Wall - ‬3 min drive
  • ‪Christy's Madison Inne - ‬17 min walk
  • ‪Madison Coffee House - ‬3 min drive

About this property

The Homestead

Beach bed & breakfast with a nearby private beach and free breakfast
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 hair salon, and a water dispenser.
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.

Similar properties

Reception

Spark by Hilton Guilford

  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
8.4 out of 10, Very Good, 36 reviews
$109 nightly
The price is $125
Oct 28 - Oct 29
Total with taxes and fees
Spark by Hilton Guilford

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

Access methods

Host will greet you

Pets

  • This property welcomes pets for USD 25 per accommodation, per night
  • Dogs only
  • 1 total (30 lbs is the maximum weight per pet)
  • Certain rooms only
  • 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 25 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 Oct 4, 2025, prices found for a 1-night stay for 2 adults at The Homestead on Nov 2, 2025 start from $309.38, excluding 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, close to Hammonasset Beach State Park, Chamard Vineyards, and Hammonasset Beach. You'll also find Guilford Town Green and Guilford Art Center within a short drive.

Will I be able to park at The Homestead?

Yes, self parking is offered for free at the bed & breakfast. Electric car charging 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.

What do couples enjoy most about The Homestead?

There are many amenities for couples at this bed u0026 breakfast, including a nearby private beach and public winery tours plus some guestrooms feature fireplaces.

Are there hot tubs at The Homestead?

No, there isn't a spa tub at this bed & breakfast.

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 25 per accommodation, per night.

Are there connecting rooms at The Homestead?

Yes, this bed & breakfast has connecting guestrooms 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 u0026 breakfast offer either a balcony or a deck 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.

Reviews

The Homestead Reviews

10

Exceptional

10/10

Cleanliness

10/10

Staff & service

9.6/10

Amenities

10/10

Property conditions & facilities

9.6/10

Eco-friendliness
Rating 10 - Excellent. 83 out of 87 reviews
Rating 8 - Good. 3 out of 87 reviews
Rating 6 - Okay. 1 out of 87 reviews
Rating 4 - Poor. 0 out of 87 reviews
Rating 2 - Terrible. 0 out of 87 reviews

Reviews

10/10 Excellent

Harvey

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This is a very lovely property located just beyond town. It's quiet and inviting. The property is beautifully maintained. The rooms are charming, with many antiques and decorations creating a very homey and fun atmosphere. The staff is very welcoming and eager to make the stay extremely pleasant. Breakfast is included and coffee and snacks are available 24/7. Our stay exceeded our expectations and will be a place to stay for future visits to the area.
Stayed 1 night in Jun 2025

10/10 Excellent

Gregory

Traveled with partner
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

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Apr 2025

10/10 Excellent

Daphne

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

10/10 Excellent

Cicek

Traveled with partner
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

10/10 Excellent

Alice

Liked: Cleanliness, property conditions & facilities
Excellent in every regard. They even have their furnishings listed on line so you can go get for yourself if you want. Staff friendly but not intrusive. Peaceful rooms. Pleasant breakfast. All around very, very nice.
Stayed 1 night in Jan 2025

10/10 Excellent

Verified traveler

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

10/10 Excellent

jeff

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

Homestead is the home away from home

The Homestead was the most welcoming. The property is stunning. The rooms are clean and chic. The sheets are the highest quality the towel warmer was top notch. Breakfast was included from a local spot. We will be back and will absolutely stay again.
Stayed 1 night in Jan 2025

10/10 Excellent

Carolyn

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

10/10 Excellent

John

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

Happy

Great people and accommodations
Stayed 2 nights in Nov 2024

10/10 Excellent

John

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

love New England

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

10/10 Excellent

Jennifer, St Louis

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The Homestead is a gem. I’ve been to countless B&Bs and Inns and few are in this category of quality, comfort and friendliness. Can’t beat the location with access to beach, hiking, boating, shopping, great dining, history… The rooms are nicely decorated with comfy beds, high end sheets (I’m picky) and nice sized bathrooms. The vitamin infused shower head with strong water pressure was amazing. Ralph and his staff bent over backward to ensure we were comfortable, well fed and prepared for whatever activity we were choosing that day. Doesn’t get better than this. I’m looking forward to my next visit.
Stayed 2 nights in Oct 2024

10/10 Excellent

Patrizia

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Oct 2024

10/10 Excellent

Rachael

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Oct 2024

10/10 Excellent

Bruce

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fabulous, uniquely decorated B&B with accommodating hosts. Luxurious beds and bedsheets, corner to corner squeaky clean. Will definitely return.
Stayed 1 night in Sep 2024

10/10 Excellent

Mark

Traveled with partner
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

10/10 Excellent

Nicholas

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Jun 2024

10/10 Excellent

Lynne

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Mar 2024

10/10 Excellent

Ken

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

10/10 Excellent

Verified traveler

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

Great for family gatherings

My family traveled together to celebrate an engagement. We booked the family suite and loved that we could all be together. The inn was charming and cozy, the staff were warm and welcoming, there is even a sweet little dog in residence! The whole place was extremely clean and well maintained, we couldn’t be happier. Next time we travel to Madison we look forward to staying at the Homestead again.
Stayed 1 night in Oct 2023

10/10 Excellent

Janine

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

Our new home away from home!

What a gem! Attentive staff and hands-on ownership. Places like The Homestead attract "like minded" people and this reminded me of why I love to travel and why I choose small boutique inns. Already planning to return with friends and stay for two nights! We loved just hanging out in our room listening to the record player. But it was equally as nice to hang out in all the other common areas; chatting with staff or guests, sitting by the fire, enjoying the various collections everywhere, selecting a book to read, nibbling on snacks (including fresh pop corn!!!), sipping some port..... And the resident doggie Hartman....you captured our hearts. You can nibble on my ear any time! And to think this place is an hour from our house. I see some more frequent quick get-aways in our future.
Stayed 1 night in Oct 2023

10/10 Excellent

Ronald, boston

Liked: Cleanliness, staff & service, property conditions & facilities
All great
Stayed 1 night in Oct 2023

10/10 Excellent

John C

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful property. Excellent management
Stayed 1 night in Sep 2023

10/10 Excellent

Leslie

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

Fabulous

Fabulous. Beautiful property and the owner was very gracious
Stayed 1 night in Sep 2023

10/10 Excellent

Coral

Liked: Staff & service
Stayed 3 nights in Jun 2023

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Flights

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Cars

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