Southold bed & breakfasts

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Best Southold bed & breakfasts

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$51 - $190$190 - $329$329 - $468$468 - $607$607+ per night

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Most recommended Southold bed & breakfasts

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Come As You Are Inn Llc - Sayville - Lounge
Come As You Are Inn Llc
Sayville, NY
9.7Wonderful(37)
Parking
Free Wi-Fi
Pool
$207+
Check availability
The Stirling House Waterfront Inn Greenport - Greenport - Building
The Stirling House Waterfront Inn Greenport
Greenport, NY
9.9Wonderful(72)
Parking
Free Wi-Fi
$530+
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Harbor Knoll Bed & Breakfast - Greenport - Dining room
Harbor Knoll Bed & Breakfast
Greenport, NY
9.8Wonderful(57)
Parking
Free Wi-Fi
Pool
$690+
Check availability
Fordham House Bed and Breakfast - Greenport - Building
Fordham House Bed and Breakfast
Greenport, NY
Free Wi-Fi
$347+
Check availability
Vine & Sand--Southold NY's Newest B&B - Southold - Living room
Vine & Sand--Southold NY's Newest B&B
Southold, NY
9.2Wonderful(3)
Parking
Free Wi-Fi
Pool
$485+
Check availability
The Farmhouse Bed & Breakfast - Cutchogue - Bedroom
The Farmhouse Bed & Breakfast
Cutchogue, NY
$607+
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A Walk in the Woods Bed and Breakfast - Southold
A Walk in the Woods Bed and Breakfast
Southold, NY
9.4Wonderful(81)
Parking
Free Wi-Fi
$405+
Check availability
Shorecrest Bed and Breakfast - Southold
Shorecrest Bed and Breakfast
Southold, NY
9.1Wonderful(64)
Free Wi-Fi
Pet friendly
$551+
Check availability
Seven Shelter Island Guest House - Shelter Island Heights
Seven Shelter Island Guest House
Shelter Island Heights, NY
9.8Wonderful(174)
Parking
Free Wi-Fi
Pool
Pet friendly
$378+
Check availability
Sweet Dreams Bed and Breakfast Cutchogue - Cutchogue
Sweet Dreams Bed and Breakfast Cutchogue
Cutchogue, NY
9.8Wonderful(66)
Parking
Free Wi-Fi
$509+
Check availability
North Fork Guest House - Cutchogue
North Fork Guest House
Cutchogue, NY
Free Wi-Fi
$51+
Check availability
Useful Info

How much is a Southold bed & breakfast?

Here are our most popular & best value bed & breakfasts

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

June
August
$405
$855
Cheapest month to stay with an average 27% drop in price.
Most expensive month to stay with an average 54% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Southold bed & breakfast deals

  • If you’re looking for a cheap bed & breakfast in Southold, you should consider going during the low season. You’ll generally find lower-priced bed & breakfasts in Southold in June and July.
  • Bed & Breakfast room prices vary depending on many factors but you’ll likely find the best bed & breakfast deals in Southold if you stay on a Sunday. The most expensive day for bed & breakfast bookings is Friday.

Where to find the best bed & breakfasts in Southold?

Our map will help you find the perfect bed & breakfast in Southold by showing you the exact location of each bed & breakfast.

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