Top B&B in Southold in 2026

Q: What are the top B&Bs in Southold?

Here are some well-liked B&Bs in the area: Vine & Sand : 4 rooms. 1.3 mi (2.1 km) from the heart of Southold. Enjoy the free buffet breakfast and designer toiletries. The Sagaponack : Situated 12 mi (19.3 km) from the heart of Southold. Harpoon House : 9 rooms. 12.4 mi (19.9 km) from the city centre. Enjoy the bars and unique decor. Westbrook Inn B&B : 9 rooms. Located 15.2 mi (24.4 km) from the core of Southold. Enjoy the free full breakfast and designer toiletries.

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Our top choices for Southold bed & breakfast

Vine & Sand

Southold

Judy

฿13,381 total

includes taxes & fees

26 Apr - 27 Apr

Harpoon House

Southampton

robert

฿8,966 total

includes taxes & fees

21 May - 22 May

The Captain Stannard

Westbrook Center

GAIL

฿8,359 total

includes taxes & fees

3 May - 4 May

The Scranton Seahorse Inn

Madison Center

Brian

฿10,170 total

includes taxes & fees

27 Apr - 28 Apr

Westbrook Inn B&B

Westbrook Center

Ashley

฿10,689 total

includes taxes & fees

27 Apr - 28 Apr

The Sagaponack

Wainscott

Dawn

฿9,701 total

includes taxes & fees

26 Apr - 27 Apr

Mill House Inn

Pantigo Road Historic District

Jessica

฿15,173 total

includes taxes & fees

3 May - 4 May

Room, 1 King Bed, Patio, Ground Floor (2) | Terrace/patio

The Homestead

Madison Center

Anthony

฿8,511 total

includes taxes & fees

27 Apr - 28 Apr

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Top Southold Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

4/10 Poor

"The hotel is in pretty rough shape. The sink rusted, the tub and mirror dirty. The garbage cans still had garbage from the previous guests. The only good part was the location "

The Sagaponack

8/10 Good

"The site manager was very helpful and responsive. When I noticed that the room wasn’t very clean and the bed sheets had hair from a previous guest, the manager quickly provided fresh sheets and a new blanket, which I really appreciated. However, the room itself could use some improvement. The shower floor was uneven with tiles that seemed to be erupting, and it was difficult to control the hot and cold water. The overall concept of the hotel was pretty cool and I liked the general vibe, but I would not choose the bungalow again. It was extremely noisy with cars passing by all night, which made it hard to sleep. With better cleaning, some maintenance on the bathroom, and improved soundproofing (or clearer information about noise levels in the bungalows), the stay could be much more comfortable."

Find out more about Southold

Southold B&B information

Number of reviews	1,386
Accommodation	30 B&B
Lowest Price	฿8,359
Highest Price	฿16,189

Frequently asked questions

Searching for B&Bs in Southold?

If you're interested in something a little more offbeat than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your getaway. If you'd like to spend some time by the water during your time in Southold, Horton Lane Beach and McCabe's Beach are worth a stop.

How do you know if a B&B is the right choice for your stay?

With attentive service, opportunities to socialise with other guests and of course a full breakfast to start the day, B&Bs offer a truly one-of-a-kind setting.

What are the top B&Bs in Southold?

Here are some well-liked B&Bs in the area: Vine & Sand: 4 rooms. 1.3 mi (2.1 km) from the heart of Southold. Enjoy the free buffet breakfast and designer toiletries. The Sagaponack: Situated 12 mi (19.3 km) from the heart of Southold. Harpoon House: 9 rooms. 12.4 mi (19.9 km) from the city centre. Enjoy the bars and unique decor. Westbrook Inn B&B: 9 rooms. Located 15.2 mi (24.4 km) from the core of Southold. Enjoy the free full breakfast and designer toiletries.

How many bed & breakfasts will I find in Southold?

Expedia has 5 B&Bs for your time in Southold.

When is the best time to book my B&B in Southold?

When you're dreaming of a escape to Southold, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Southold is 1452 mm.

What is there to do in Southold?

If you're looking for some activities to entertain you on your trip, consider visiting Sparkling Pointe and Mattebella Vineyards. You should put Croteaux Vineyards and Horton Lane Beach on your list if you want to see more of the area.

How can I get to and around Southold?

Mapping out your trip in and around Southold is easy with these transportation options. Fly into East Hampton, NY (HTO), which is located 11.8 mi (18.9 km) from the heart of the city. Otherwise, you can search for flights to Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away. If you'd like to venture out around the area, consider renting a car to explore more sights.

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