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Book Town of Southold Town Bed & Breakfast

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Check prices for these dates

Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21
In one month
Jan 2 - Jan 4
In two months
Jan 30 - Feb 1

Top Cities in Town of Southold Town

Beautiful spot on the #longisland sound surfing
B&BB&B

Greenport

Greenport

B&B in Town of Southold Town

Living area
Harbor Knoll Bed & Breakfast

Harbor Knoll Bed & Breakfast

3.0 star property
Pipes Cove
9.2 out of 10, Wonderful, (12)
"It was very pleasant. We would stay again someday. Very convenient to restaurants in town and ferry. "
United States
Andrea
Harbor Knoll Bed & Breakfast
Beach/ocean view
Stirling House Bed & Breakfast

Stirling House Bed & Breakfast

3.0 star property
Greenport
9.8 out of 10, Exceptional, (24)
"Our stay was only 2 nights but felt like 5. Well rested 3 days. Would return in a Heart Beat. Clay was awesome and the breakfasts were over the top !"
United States
Adam
Stirling House Bed & Breakfast
Exterior
Arbor View House B&B

Arbor View House B&B

3.5 star property
East Marion
9.2 out of 10, Wonderful, (15)
"Two mid age couples just had a good and relaxing time with great hospitality. "
United States
Michail
Arbor View House B&B
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
$320 nightly
The price is $366
Dec 16 - Dec 17
Total with taxes and fees
Vine & Sand
Living area
The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast

4.0 star property
Cutchogue
10.0 out of 10, Exceptional, (13)
"very comfortable stay. "
United States
Valentine
The Farmhouse Bed and 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.
$367 nightly
The price is $420
Jan 1 - Jan 2, 2026
Total with taxes and fees
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 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.
$403 nightly
The price is $460
Jan 1 - Jan 2, 2026
Total with taxes and fees
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 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
$403 nightly
The price is $460
Jan 1 - Jan 2, 2026
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite 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

Southold
$367 nightly
The price is $420
Jan 1 - Jan 2, 2026
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Exterior
Fordham House

Fordham House

3.0 star property
Greenport
10.0 out of 10, Exceptional, (16)
"Fantastic couple runs this B&B. Very nice, helpful and accommodating!!!!!!! Beautiful House, Great Breakfast, Nice Area & Wonderful Hosts!"
United States
John
Fordham House
Exterior
North Fork Guest House

North Fork Guest House

3.5 star property
Cutchogue
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."
United States
Bernard
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 Town of Southold Town Hotel Reviews

The Menhaden

The Menhaden

10/10 Excellent
"Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! "
Cory 1-night trip
Posted 5 days ago
The Menhaden

Find out more about Town of Southold Town

Town of Southold Town B&B information

Number of reviews
77
Accommodation
11 B&B
Lowest Price
$366
Highest Price
$460

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