Bed and Breakfast and Inn in Southold, NY

17 available b&b offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Southold, NY B&B
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

17 Bed and Breakfasts and Inn in Southold, NY

Best Southold, NY bed and breakfasts with breakfast included

Vine & Sand--southold Ny's Newest B&b - Southold, NY
9.4 7 reviews
Southold, NY
05/07 – 09/07
$1929/nighttotal: $7716 (4 )

Vine & Sand--southold Ny's Newest B&b

2 4
B&B , Peconic
Vine & Sand is a charming bed and breakfast located in Southold, a picturesque town on Long Island's North Fork, just 32 kilometres from Splish Splash water park and 67 kilometres from Long Island MacArthur Airport.
The B&B offers a peaceful retreat for couples, with a private bedroom and bathroom, a terrace and a garden. Guests can enjoy a range of amenities including a swimming pool, a hot tub, and free parking, as well as a delicious breakfast each morning.
Arbor View House Bed And Breakfast - Southold, NY
9.3 34 reviews
Southold, NY
05/07 – 09/07
$1672/nighttotal: $6688 (4 )

Arbor View House Bed And Breakfast

2 4
B&B , East Marion
Arbor View House Bed and Breakfast is situated in East Marion, Long Island, just a short distance from Island End Golf and Country Club, the Railroad Museum of Long Island, and Hortons Point Lighthouse. The property has received excellent ratings for its location, cleanliness, and overall experience.
The guest house offers a single bedroom with a private bathroom, accommodating up to two guests. Enjoy a range of amenities including a swimming pool, Jacuzzi, terrace, garden, spa, fitness centre, and tennis court, alongside a delicious breakfast and free Wi-Fi.
Harbor Knoll Bed And Breakfast - Southold, NY
9.7 30 reviews
Southold, NY
05/07 – 09/07
$3513/nighttotal: $14052 (4 )

Harbor Knoll Bed And Breakfast

3 4
B&B , Greenport
Harbor Knoll Bed and Breakfast is situated in Greenport, a short distance from the town's beaches and within easy reach of attractions like Splish Splash, just 26 miles away. The property enjoys excellent ratings for location, cleanliness, and overall guest satisfaction.
The guest house offers comfortable accommodation with a choice of rooms featuring a private bathroom and a floor area of 21 square meters. Guests can enjoy a variety of amenities, including a swimming pool, a tennis court, a garden, a terrace, and a bar, as well as free Wi-Fi and parking.

Best Southold, NY bed and breakfasts with a pool

Among the 17 accommodations in Southold, NY, here are the 3 best b&b with a pool

Harbor Knoll Bed And Breakfast - Southold, NY
9.7 30 reviews
Southold, NY
05/07 – 09/07
$3513/nighttotal: $14052 (4 )

Harbor Knoll Bed And Breakfast

3 4
B&B , Greenport
Harbor Knoll Bed and Breakfast is situated in Greenport, a short distance from the town's beaches and within easy reach of attractions like Splish Splash, just 26 miles away. The property enjoys excellent ratings for location, cleanliness, and overall guest satisfaction.
The guest house offers comfortable accommodation with a choice of rooms featuring a private bathroom and a floor area of 21 square meters. Guests can enjoy a variety of amenities, including a swimming pool, a tennis court, a garden, a terrace, and a bar, as well as free Wi-Fi and parking.
Cowgirl Palace - Southold, NY
9.0 120 reviews
Southold, NY
05/07 – 09/07
$2217/nighttotal: $8868 (4 )

Cowgirl Palace

3 4
B&B , Wainscott
Cowgirl Palace is located in Sag Harbor, a short drive from Wainscott, with Montauk Point Lighthouse 14 miles away and Second House Museum 19 miles away. The property has excellent ratings for location, cleanliness, and overall user experience.
The guesthouse offers a comfortable and convenient stay with a private bathroom, air conditioning, and a flat-screen TV. Guests can enjoy a range of amenities, including a swimming pool, a hot tub, a tennis court, a garden, and a terrace.
Vine & Sand--southold Ny's Newest B&b - Southold, NY
9.4 7 reviews
Southold, NY
05/07 – 09/07
$1929/nighttotal: $7716 (4 )

Vine & Sand--southold Ny's Newest B&b

2 4
B&B , Peconic
Vine & Sand is a charming bed and breakfast located in Southold, a picturesque town on Long Island's North Fork, just 32 kilometres from Splish Splash water park and 67 kilometres from Long Island MacArthur Airport.
The B&B offers a peaceful retreat for couples, with a private bedroom and bathroom, a terrace and a garden. Guests can enjoy a range of amenities including a swimming pool, a hot tub, and free parking, as well as a delicious breakfast each morning.

Frequently Asked Questions about bed and breakfast in Southold, NY

Destinations nearby

Best Southold, NY bed and breakfasts with a garden

Zey Hotel - Southold, NY
8.5 257 reviews
Southold, NY
05/07 – 09/07
$2001/nighttotal: $8004 (4 )

Zey Hotel

3 4
B&B , Greenport
ZEY HOTEL is situated in Greenport, a charming village on Long Island's North Fork, just 26 miles from Splish Splash water park and 48 miles from Long Island MacArthur Airport. The hotel has received very good user ratings, with excellent marks for its location and cleanliness.
This one-bedroom guesthouse features a private bathroom with bathrobes, slippers, and a hairdryer. Guests can enjoy a range of amenities, including a terrace, garden, picnic area, lounge, and free bikes.
Harbor Knoll Bed And Breakfast - Southold, NY
9.7 30 reviews
Southold, NY
05/07 – 09/07
$3513/nighttotal: $14052 (4 )

Harbor Knoll Bed And Breakfast

3 4
B&B , Greenport
Harbor Knoll Bed and Breakfast is situated in Greenport, a short distance from the town's beaches and within easy reach of attractions like Splish Splash, just 26 miles away. The property enjoys excellent ratings for location, cleanliness, and overall guest satisfaction.
The guest house offers comfortable accommodation with a choice of rooms featuring a private bathroom and a floor area of 21 square meters. Guests can enjoy a variety of amenities, including a swimming pool, a tennis court, a garden, a terrace, and a bar, as well as free Wi-Fi and parking.
Vine & Sand--southold Ny's Newest B&b - Southold, NY
9.4 7 reviews
Southold, NY
05/07 – 09/07
$1929/nighttotal: $7716 (4 )

Vine & Sand--southold Ny's Newest B&b

2 4
B&B , Peconic
Vine & Sand is a charming bed and breakfast located in Southold, a picturesque town on Long Island's North Fork, just 32 kilometres from Splish Splash water park and 67 kilometres from Long Island MacArthur Airport.
The B&B offers a peaceful retreat for couples, with a private bedroom and bathroom, a terrace and a garden. Guests can enjoy a range of amenities including a swimming pool, a hot tub, and free parking, as well as a delicious breakfast each morning.
Arbor View House Bed And Breakfast - Southold, NY
9.3 34 reviews
Southold, NY
05/07 – 09/07
$1672/nighttotal: $6688 (4 )

Arbor View House Bed And Breakfast

2 4
B&B , East Marion
Arbor View House Bed and Breakfast is situated in East Marion, Long Island, just a short distance from Island End Golf and Country Club, the Railroad Museum of Long Island, and Hortons Point Lighthouse. The property has received excellent ratings for its location, cleanliness, and overall experience.
The guest house offers a single bedroom with a private bathroom, accommodating up to two guests. Enjoy a range of amenities including a swimming pool, Jacuzzi, terrace, garden, spa, fitness centre, and tennis court, alongside a delicious breakfast and free Wi-Fi.

Best Southold, NY bed and breakfasts with air conditioning

Cowgirl Palace - Southold, NY
9.0 120 reviews
Southold, NY
05/07 – 09/07
$2217/nighttotal: $8868 (4 )

Cowgirl Palace

3 4
B&B , Wainscott
Cowgirl Palace is located in Sag Harbor, a short drive from Wainscott, with Montauk Point Lighthouse 14 miles away and Second House Museum 19 miles away. The property has excellent ratings for location, cleanliness, and overall user experience.
The guesthouse offers a comfortable and convenient stay with a private bathroom, air conditioning, and a flat-screen TV. Guests can enjoy a range of amenities, including a swimming pool, a hot tub, a tennis court, a garden, and a terrace.
Vine & Sand--southold Ny's Newest B&b - Southold, NY
9.4 7 reviews
Southold, NY
05/07 – 09/07
$1929/nighttotal: $7716 (4 )

Vine & Sand--southold Ny's Newest B&b

2 4
B&B , Peconic
Vine & Sand is a charming bed and breakfast located in Southold, a picturesque town on Long Island's North Fork, just 32 kilometres from Splish Splash water park and 67 kilometres from Long Island MacArthur Airport.
The B&B offers a peaceful retreat for couples, with a private bedroom and bathroom, a terrace and a garden. Guests can enjoy a range of amenities including a swimming pool, a hot tub, and free parking, as well as a delicious breakfast each morning.
Zey Hotel - Southold, NY
8.5 257 reviews
Southold, NY
05/07 – 09/07
$2001/nighttotal: $8004 (4 )

Zey Hotel

3 4
B&B , Greenport
ZEY HOTEL is situated in Greenport, a charming village on Long Island's North Fork, just 26 miles from Splish Splash water park and 48 miles from Long Island MacArthur Airport. The hotel has received very good user ratings, with excellent marks for its location and cleanliness.
This one-bedroom guesthouse features a private bathroom with bathrobes, slippers, and a hairdryer. Guests can enjoy a range of amenities, including a terrace, garden, picnic area, lounge, and free bikes.
Harbor Knoll Bed And Breakfast - Southold, NY
9.7 30 reviews
Southold, NY
05/07 – 09/07
$3513/nighttotal: $14052 (4 )

Harbor Knoll Bed And Breakfast

3 4
B&B , Greenport
Harbor Knoll Bed and Breakfast is situated in Greenport, a short distance from the town's beaches and within easy reach of attractions like Splish Splash, just 26 miles away. The property enjoys excellent ratings for location, cleanliness, and overall guest satisfaction.
The guest house offers comfortable accommodation with a choice of rooms featuring a private bathroom and a floor area of 21 square meters. Guests can enjoy a variety of amenities, including a swimming pool, a tennis court, a garden, a terrace, and a bar, as well as free Wi-Fi and parking.
©2026 cozycozy.com