The Homestead | Bed & Breakfast in Madison

Q: How much does it cost per night to stay in The Homestead?

Best-rates for the The Homestead starts from $462 per night with includes Air Conditioner, Parking, Pet Friendly, TV, View, Ocean View, Balcony/Terrace, Oceanfront, Security/Safety, EV Charge Station, Sports/Activities, Fireplace/Heating, Guest Services, Entertainment, Breakfast, Child Friendly, Internet StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

| 9.5 (91 Reviews) | Pet Friendly 11 Bedrooms 11 Bathrooms 31 Guests

Madison Center Bed & Breakfast | The Homestead

11 Bedroom Bed & Breakfast in Madison Center, Madison

The Homestead features air-conditioned accommodations in Madison. 13 miles from Thimble Islands and 17 miles from City Hall, the property offers free bikes and a garden. There's a sun terrace and guests can make use of free Wifi, free private parking, and an electric vehicle charging station. At the bed and breakfast, units include a wardrobe, a flat-screen TV, a private bathroom, bed linen, and towels. A balcony with an outdoor dining area and quiet street views is offered in some units. The rooms are equipped with heating facilities. A selection of options including warm dishes, local specialities, and fresh pastries are available for the buffet breakfast. There is a snack bar and lounge. Guests can also warm up near the outdoor fireplace after a day of cycling. Yale University is 18 miles from the bed and breakfast, while The Yale Bowl is 20 miles from the property. Tweed-New Haven Airport is 16 miles away.

The Homestead is located in Madison.

This 11 Bedrooms Bed & Breakfast is suitable for tourists and travelers. It has several amenities that would guarantee your comfort. These amenities include: Air Conditioner, Parking, Pet Friendly, and several others. This is a 4 star rated property and has over 91 reviews with the average score of 9.5 . Coming to Madison and needing a place to stay? Be it for work or for leisure, consider staying at this Bed & Breakfast for your next visit, you will surely love it.

You can check the reviews and description of this 11 Bedrooms Bed & Breakfast if you want to learn more about this StayAndPlay.com place in Madison. These details are authentic, as they are provided by our partner, booking.com.

This The Homestead in Madison is well equipped and has all facilities that have been listed below. Please note that these details were shared to us by booking.com for the listed “The Homestead”. We solely rely on their shared details and are regarded as “accurate”. If you have any concerns about the information or accuracy describing this Bed & Breakfast, please let us know.

Unique Amenities

Air Conditioner
Parking
Pet Friendly
TV
View
Ocean View
Balcony/Terrace
Oceanfront
Security/Safety
EV Charge Station
Sports/Activities
Fireplace/Heating
Guest Services
Entertainment
Breakfast
Child Friendly
Internet

Policies

Check-in The minimum age for check-in is 21

Cancellation policy Free cancellation

Pet Policy Pets are allowed upon request and charges may apply.

Other Policy Please note, guests can be given day passes to access a beach that belongs to a private beach hotel.guests are required to show a photo id and credit card upon check-in. please note that all special requests are subject to availability and additional charges may apply, please inform of your expected arrival time in advance. you can use the special requests box when booking, or contact the property directly using the contact details in your confirmation, this property does not accommodate bachelor(ette) or similar parties, guests under the age of 18 can only check in with a parent or official guardian.

391 Boston Post Road, Madison, CT 06443, USA

What Our Guests say 500 + Reviews

Jun 11, 2026 07:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Stettin, USA

May 4, 2026 07:00:00 AM

Reviewer Type: Extended Group

Travel Purpose: leisure

Positive: Went for sister's 50th birthday weekend. Staff, location and Inn exceeded expectations. Highly recommend The Homestead!

Summary: Want go be treated well,

Hanson, USA

Apr 23, 2026 07:00:00 AM

Reviewer Type: Extended Group

Travel Purpose: leisure

Positive: The property was gorgeous, very thoughtfully planned and decorated.

Negative: Nothing. Exceeded my high expectations.

Summary: Wished we could’ve stayed longer!

JoAnna, USA

Apr 19, 2026 07:00:00 AM

Reviewer Type: Solo Traveller

Travel Purpose: leisure

Lori, USA

Feb 15, 2026 08:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Positive: We loved the attention to detail, character of the inn and friendliness of the hosts. We will be back!

Karen, USA

Jan 2, 2026 08:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Positive: Impeccably clean and homey feel. The staff welcomed us like family. Breakfast options were many and everything was delicious

Summary: Great getaway spot to get a shot of new england charm.

Sarah, USA

Dec 23, 2025 08:00:00 AM

Reviewer Type: Solo Traveller

Travel Purpose: leisure

Deragon, Indonesia

Sep 5, 2025 07:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Positive: The Homestead is a warm, homey, classy establishment. The inn keepers, Ellen, Kate and Ray, provided anything we wanted and were engaging, yet we hardly knew they were there! For breakfast we enjoyed their homemade peach scones and egg bites, delicious quiche, zucchini bread, fresh fruit, cereal, yogurt, juice and espresso drinks. They also had snacks and drinks available anytime. Our room was large, bright, quiet and comfortable. All of the public rooms were decorated traditionally with many whimsical touches. We spent time on the back patio with a gas fire pit, and in the front yard, that had 3 separate seating areas. They provided beach towels and chairs, and we rode their bikes to Hammoneset beach.

Negative: What’s not to like?

Summary: We didn’t want to leave!

Anne, USA

Sep 2, 2025 07:00:00 AM

Reviewer Type: Extended Group

Travel Purpose: leisure

Positive: Wonderful experience and the owner personally greeted us and spent time with us. The visit felt like we were with family but with all the comforts of a 5-star luxury hotel.

Negative: I wish we had planned to stay longer.

Summary: Amazing! Highly recommend.

Boriana, USA

Aug 29, 2025 07:00:00 AM

Reviewer Type: Family With Children

Travel Purpose: business

Positive: Everything is thought of, the rooms are all ample, and extremely well appointed. Every little thing is thought of. The common areas are really cozy and there is something from everyone, from music to great books and entertainment. The staff and owner born and raised in Madison and know where to go and what to do. It's a real find, and you'll be as happy as we were I assure you. The little touches are great too, fresh fruit from local farms, snacks, coffee, drinks all available compliments of the house throughout the day, and at night some delicious cookies and port are out to enjoy.

Negative: Nothing. The place is so well run, thought out and considered. The staff and owner are the best. Brit and Saul are truly special people who made our stay so comfortable and enjoyable. Thank you!

Summary: Perfect. Great rooms and outdoor area as well as cozy common areas and a delicious breakfast.

Jason, USA

FAQ's

Is this The Homestead pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

What time is check-in & check-out at The Homestead?

Check-in time for The Homestead starts counting from 3:00 PM and check-out is until 11:00 AM. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Does the The Homestead have a swimming pool?

No, this The Homestead does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in The Homestead?

Best-rates for the The Homestead starts from $462 per night with includes Air Conditioner, Parking, Pet Friendly, TV, View, Ocean View, Balcony/Terrace, Oceanfront, Security/Safety, EV Charge Station, Sports/Activities, Fireplace/Heating, Guest Services, Entertainment, Breakfast, Child Friendly, Internet StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is The Homestead a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this bed & breakfast 4 stars or guests have recommended them suitable for families. As reported by the owner or manager, the bed & breakfast has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the The Homestead wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the The Homestead has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the The Homestead?

Based on the information reported by the owner or manager, the The Homestead indicates 1 day stay policy at this bed & breakfast. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for The Homestead?

Based on the information reported by the owner or manager, details for the cancellation policy for the The Homestead are as follows: Free cancellation Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Check Bed & Breakfast Availability

Nightly rates from:

US $462