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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Madison bed & breakfast

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

The Homestead

3.0 star property
Madison Center
10.0 out of 10, Exceptional, (89)
"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!"
United States
Cynthia
The price is AED 930
AED 1,032 total
includes taxes & fees
4 Jan - 5 January 2026
The Homestead
IPod dock, MP3 dock
The Captain Stannard

The Captain Stannard

3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (258)
"The Inn and staff were warm and welcoming, the facility exceptionally clean. Breakfast exceeded my expectations for a continental breakfast! Would absolutely stay again! "
United States
Lisa
The Captain Stannard
Terrace/patio
Westbrook Inn B&B

Westbrook Inn B&B

3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (175)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is AED 791
AED 878 total
includes taxes & fees
14 Dec - 15 Dec
Westbrook Inn B&B
Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board
James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4.0 star property
Old Saybrook Center
9.2 out of 10, Wonderful, (22)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
United States
Rachel
The price is AED 1,109
AED 1,231 total
includes taxes & fees
11 Dec - 12 Dec
James Pharmacy Bed & Breakfast
Interior entrance
Vine & Sand

Vine & Sand

3.0 star property
Southold
9.6 out of 10, Exceptional, (13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
Vine & Sand
Interior
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Southold
10.0 out of 10, Exceptional, (1)
"Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great...
United States
Jessica P.
The price is AED 1,307
AED 1,691 total
includes taxes & fees
1 Jan - 2 January 2026
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Seasonal outdoor pool, pool umbrellas, sun loungers
The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast

3.5 star property
East Hampton
9.6 out of 10, Exceptional, (81)
"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. "
United States
Juliette
The price is AED 859
AED 954 total
includes taxes & fees
6 Jan - 7 January 2026
The Bevin House Bed & Breakfast
Interior
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Southold
10.0 out of 10, Exceptional, (1)
"Great experience. Wonderful hosts. "
United States
Mark L.
The price is AED 1,192
AED 1,542 total
includes taxes & fees
1 Jan - 2 January 2026
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Property grounds
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

Hamden
The price is AED 2,314
AED 3,560 total
includes taxes & fees
11 Dec - 12 Dec
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Exterior
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Southold
The price is AED 1,192
AED 1,542 total
includes taxes & fees
1 Jan - 2 January 2026
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Interior
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Southold
The price is AED 1,307
AED 1,691 total
includes taxes & fees
1 Jan - 2 January 2026
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
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

Homewood Suites by Hilton Orange New Haven

Homewood Suites by Hilton Orange New Haven

10/10 Excellent
"My stay was amazing the hotel suite provided a lot of convenience with the kitchen & smart tv. The gym was also pretty great & was able to get my workouts in. I also, admire that my stay was very quiet & relaxing with hardly any noise on my floor. I would absolutely book this hotel again. "
George 3-night trip
Posted 1 day ago
Homewood Suites by Hilton Orange New Haven

Frequently asked questions

Searching for B&Bs in Madison?
If you're looking for something a little quirkier than the traditional hotel experience, a bed and breakfast could be a great option for your trip. If you're hoping to spend some time walking along the water in Madison, Hammonasset Beach is worth a visit.
Are you thinking about a B&B for your stay?
With attentive service, opportunities to socialize with other guests, and of course a full breakfast, B&Bs offer a unique 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 deli and unique décor. The Captain Stannard: 11 rooms. 6.4 mi (10.3 km) from the downtown core. Enjoy the private yard and unique décor. Westbrook Inn B&B: 9 rooms. Situated 6.3 mi (10.1 km) from the heart of Madison. Enjoy the free full breakfast and designer toiletries. James Pharmacy Bed & Breakfast: 3 rooms. Located 10.4 mi (16.7 km) from the core of Madison. Enjoy the local cuisine breakfast and designer toiletries.
What's the best time of year to book my B&B in Madison?
When you're dreaming of a stay in Madison, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 35°F. Average annual precipitation for Madison is 54 inches.
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 might put Hammonasset Beach State Park and Allis-Bushnell House and Museum on your list if you want to see more of the area.
How can I get to and around Madison?
Mapping out your trip in and around Madison is easy 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 center. 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, you may want to rent a car for your trip.