Southold bed & breakfasts

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Recommended by KAYAK

Best Southold bed & breakfasts

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$51 - $194$194 - $336$336 - $479$479 - $621$621+ per night

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Most recommended Southold bed & breakfasts

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Shorecrest Bed and Breakfast - Southold - Bedroom
Shorecrest Bed and Breakfast
Southold, NY
9.1Wonderful(64)
Free Wi-Fi
Pet friendly
$551+
Check availability
Harbor Knoll Bed & Breakfast - Greenport - Dining room
Harbor Knoll Bed & Breakfast
Greenport, NY
8.5Very good(54)
Parking
Free Wi-Fi
Pool
$758+
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Come As You Are Inn Llc - Sayville - Lounge
Come As You Are Inn Llc
Sayville, NY
9.7Wonderful(32)
Parking
Free Wi-Fi
Pool
$287+
Check availability
North Fork Guest House - Cutchogue - Building
North Fork Guest House
Cutchogue, NY
Free Wi-Fi
$51+
Check availability
Fordham House Bed and Breakfast - Greenport - Bedroom
Fordham House Bed and Breakfast
Greenport, NY
Free Wi-Fi
$347+
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The Stirling House Waterfront Inn Greenport - Greenport - Balcony
The Stirling House Waterfront Inn Greenport
Greenport, NY
10Wonderful(69)
Parking
Free Wi-Fi
$609+
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Vine & Sand--Southold NY's Newest B&B - Southold - Living room
Vine & Sand--Southold NY's Newest B&B
Southold, NY
9.0Wonderful(3)
Parking
Free Wi-Fi
Pool
$680+
Check availability
The Farmhouse Bed & Breakfast - Cutchogue - Bedroom
The Farmhouse Bed & Breakfast
Cutchogue, NY
$563+
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A Walk in the Woods Bed and Breakfast - Southold
A Walk in the Woods Bed and Breakfast
Southold, NY
8.9Very good(81)
Parking
Free Wi-Fi
$405+
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Sweet Dreams Bed and Breakfast Cutchogue - Cutchogue
Sweet Dreams Bed and Breakfast Cutchogue
Cutchogue, NY
9.8Wonderful(65)
Parking
Free Wi-Fi
$566+
Check availability
Seven Shelter Island Guest House - Shelter Island Heights
Seven Shelter Island Guest House
Shelter Island Heights, NY
9.7Wonderful(168)
Parking
Free Wi-Fi
Pool
Pet friendly
$718+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

June
August
$405
Cheapest month to stay with an average 7% drop in price.
Most expensive month to stay with an average 17% rise in price.
Average Sun - Thu 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.
  • If you want to ensure you grab a bargain, try to book more than 90 days before your stay to get the best price for a Southold bed & breakfast.
  • Don’t know how much time you need to see all the sights? KAYAK users usually book their bed & breakfast in Islip for 1 day.

FAQs when booking a bed & breakfast in Southold

  • What are the best bed & breakfasts near Custer Observatory?

    Custer Observatory is a popular area in Southold and there are many bed & breakfasts closeby. Check out Wickham Prince Bed And Breakfast or Vine & Sand--Southold NY's Newest B&B for hostels recommended by KAYAK that are within walking distance of Custer Observatory.

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.

Everything you need to know for your stay in Southold

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