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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

B&B in Madison

The Captain Stannard
IPod dock, MP3 dock

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (233)
"Everything was fantastic, will stay again!"
The Captain Stannard
The Homestead
Room, 1 King Bed, Patio, Ground Floor (7) | 1 bedroom, Egyptian cotton sheets, premium bedding, down comforters

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (80)
"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 "
The Homestead
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
Vine & Sand
Interior entrance

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (7)
"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 Bevin House Bed & Breakfast
Seasonal outdoor pool, pool umbrellas, sun loungers

The Bevin House Bed & Breakfast

3.5 star property
9.6 out of 10, Exceptional, (77)
"Welcoming, fun, and absolutely stunning! A cuddly turkey didn’t hurt either. "
The price is AED 955
AED 1,060 total
includes taxes & fees
21 Jul - 22 Jul
The Bevin House Bed & Breakfast
West Neck Guesthouse
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very Good, (32)
"Very convenient location next to Cresent Beach and Leon 1909 restaurant which is fantastic! "
The price is AED 1,151
AED 1,316 total
includes taxes & fees
31 Jul - 1 Aug
West Neck Guesthouse
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
James Pharmacy Bed & Breakfast
Miss Anna James Room | 1 bedroom, individually decorated, individually furnished

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
The price is AED 1,499
AED 2,104 total
includes taxes & fees
22 Jul - 23 Jul
James Pharmacy Bed & Breakfast
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (152)
"Beautiful bed and breakfast with plush robes and slippers, super clean, would stay again!"
The price is AED 1,052
AED 1,167 total
includes taxes & fees
20 Jul - 21 Jul
Westbrook Inn B&B
The Farmhouse Bed and Breakfast
Living area

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (12)
"Lovely B&B run by a lovely couple"
The Farmhouse Bed and 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
Higganum House B&B
Exterior

Higganum House B&B

3.0 star property
Higganum House B&B
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Property grounds

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

The price is AED 2,314
AED 3,582 total
includes taxes & fees
20 Jul - 21 Jul
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Thimble Islands Bed & Breakfast
Porch

Thimble Islands Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (4)
Thimble Islands Bed & Breakfast
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
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
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
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
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite 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
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Interior

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

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...
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
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
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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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. Vine & Sand: 4 rooms. Located 18.4 mi (29.5 km) from the core of Madison. Enjoy the free buffet 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 North Madison Shopping Center 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.