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Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Featured B&B in Madison

Our top choices for Madison bed & breakfast

The Captain Stannard
IPod dock, MP3 dock

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (243)
"Everything was fantastic, will stay again!"
The Captain Stannard
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (159)
"Charming, beautiful inn; excellent food and service."
The price is S$316
includes taxes & fees
23 Sept - 24 Sept
Westbrook Inn B&B
West Neck Guesthouse
Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

3.5 star property
8.2 out of 10, Very good, (36)
"Great property! Close to beach and super clean. "
The price is S$459
includes taxes & fees
1 Sept - 2 Sept
West Neck Guesthouse
Vine & Sand
Interior entrance

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (9)
"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. "
Vine & Sand
The Homestead
Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (84)
"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!"
The price is S$480
includes taxes & fees
27 Aug - 28 Aug
The Homestead
James Pharmacy Bed & Breakfast
1 bedroom, individually decorated, individually furnished

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Beautiful property in a great location, convenient to everything.Our room was clean and comfortable."
The price is S$580
includes taxes & fees
27 Aug - 28 Aug
James Pharmacy Bed & Breakfast
The Bevin House Bed & Breakfast
Seasonal outdoor pool, pool umbrellas, pool loungers

The Bevin House Bed & Breakfast

3.5 star property
9.6 out of 10, Exceptional, (78)
"The staff was super friendly and welcoming. The house was beautiful and the grounds full of things to explore. The breakfast was presently with panache and tasted great. We swam in the pool, ate at local restaurants, pet a turkey, and visited the local winery. I would highly recommend this establishment. "
The price is S$350
includes taxes & fees
27 Aug - 28 Aug
The Bevin House Bed & Breakfast
Harbor Knoll Bed & Breakfast
Living area

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (10)
"Beautiful bed and breakfast with gorgeous views. Close to shops and restaurants but far enough to be private and quiet. Will definitely be coming back"
Harbor Knoll Bed & Breakfast
Arbor View House B&B
Exterior

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (15)
"Two mid age couples just had a good and relaxing time with great hospitality. "
Arbor View House B&B
Stirling House Bed & Breakfast
Beach/ocean view

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (23)
"Very comfortable king size bed. Excellent gourmet breakfast, discreet host. Older house, but all the comforts. Absolutely every need provided for. "
Stirling House Bed & Breakfast
Jay's Ranch
Exterior

Jay's Ranch

4.0 star property
7.6 out of 10, Good, (44)
"This was an amazing stay. Renee is a great host. She is clean, personable, and professional. The home is very cozy, and while still a work in progress, the outdoor area is beautiful and teeming with potential. This is not a hotel or a motel, understanding this, do not expect the starchy atmosphere of those places, but instead appreciate the friendly, homely vibe. If you’re looking for somewhere reasonably priced, clean, and cozy, this is a great spot."
Jay's Ranch
Higganum House B&B
Exterior

Higganum House B&B

3.0 star property
Higganum House B&B
Thimble Islands Bed & Breakfast
Porch

Thimble Islands Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (4)
"A beautiful, quiet home in a stunning setting run by two extremely gracious hosts. Breakfast on both days was excellent."
Thimble Islands Bed & Breakfast
The Farmhouse Bed and Breakfast
Living area

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (13)
"very comfortable stay. "
The Farmhouse Bed and Breakfast
SEVEN - Shelter Island Guest House
Kayaking

SEVEN - Shelter Island Guest House

2.5 star property
9.8 out of 10, Exceptional, (57)
"It was a beautiful place! Under construction however, Beth was Amazing! Amelia was so hospitable. Close to everything and it certainly helped that the weather was spectacular! Will definitely go back another time!"
SEVEN - Shelter Island Guest House
Fordham House
Exterior

Fordham House

3.0 star property
10.0 out of 10, Exceptional, (16)
Fordham House
North Fork Guest House
Exterior

North Fork Guest House

3.5 star property
9.8 out of 10, Exceptional, (10)
"Beautifully renovated b & b within walking distance of at least 4 wineries. Our hosts were attentive without being intrusive, made off the charts breakfast and were super knowledgeable about the area. The house was modern and comfortable. I left envious of the fresh, warm decor. We would love to come back in the spring or summer! Highly, highly recommended."
North Fork Guest House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Madison Hotel Reviews

The Blake Hotel

The Blake Hotel

10/10 Excellent
"Great for Yale "
Philip 2-night trip
Posted 10 hours ago
The Blake Hotel

Find out more about Madison

Find out more about Madison

Madison B&B information

Number of reviews
444
Accommodation
17 B&B
Lowest Price
S$316
Highest Price
S$580

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Explore a world of travel with Expedia

Frequently asked questions

Searching for B&Bs in Madison?
If you're interested in something a little quirkier than your standard hotel experience, a stay at a bed and breakfast could be the perfect alternative for your getaway. If you're hoping to spend some time walking along the water in Madison, Hammonasset Beach is worth a visit.
Are you interested in an apartment for your stay?
With attentive service, opportunities to meet guests from other places and of course a full breakfast, B&Bs offer a one-of-a-kind environment.
What are the best B&Bs in Madison?
Here are some B&Bs in the area: The Homestead: 10 rooms. 2.4 mi (3.8 km) from the heart of Madison. Enjoy the snack bar/deli and unique decor. The Captain Stannard: 11 rooms. 6.4 mi (10.3 km) from the city centre. Enjoy the private garden and unique decor. Vine & Sand: 4 rooms. Located 18.4 mi (29.5 km) from the core of Madison. Enjoy the free buffet breakfast and designer toiletries.
When is the best time to book my B&B in Madison?
When you're dreaming of a escape to Madison, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Madison is 1382 mm.
What is there to do in Madison?
Spend some time exploring Hammonasset Beach and Meigs Point Nature Center if you're hoping to see some of the area's natural features. You should put Hammonasset Beach State Park and North Madison Shopping Center on your list if you want to see more of the area.
How can I get to and around Madison?
You can plan your excursions in and around Madison ahead of time with these transportation options. Fly into New Haven, CT (HVN-Tweed - New Haven Regional), which is located 16.5 mi (26.5 km) from the city centre. You can also search for flights into New London, CT (GON-Groton - New London), which is 27.6 mi (44.4 km) away. If you'd like to venture out around the area, consider renting a car to explore more sights.