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. Mill House Inn : 10 rooms. Located 14.4 mi (23.1 km) from the core of Southold. Enjoy the free cooked breakfast and designer toiletries.

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Our top choices for Southold bed & breakfast

Vine & Sand

Southold

Judy

Rp7.541.667 total

includes taxes & fees

9 Apr - 10 Apr

The Captain Stannard

Westbrook Center

GAIL

Rp4.041.410 total

includes taxes & fees

13 Apr - 14 Apr

Westbrook Inn B&B

Westbrook Center

Beth

Rp4.183.269 total

includes taxes & fees

8 Apr - 9 Apr

Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board

James Pharmacy Bed & Breakfast

Old Saybrook Center

Isolde

Rp5.123.885 total

includes taxes & fees

27 Apr - 28 Apr

Harpoon House

Southampton

robert

Rp4.728.665 total

includes taxes & fees

9 Apr - 10 Apr

The Sagaponack

Wainscott

Anne

Rp4.066.837 total

includes taxes & fees

26 Apr - 27 Apr

Mill House Inn

Pantigo Road Historic District

Eliane

Rp6.935.481 total

includes taxes & fees

8 Apr - 9 Apr

The Scranton Seahorse Inn

Madison Center

David

Rp4.425.840 total

includes taxes & fees

11 Apr - 12 Apr

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Top Southold Hotel Reviews

Sound View Greenport

8/10 Good

"Bathroom very clean. Staff is super friendly. Ate at the restaurant and it was delicious. "

Quality Inn Old Saybrook - Westbrook

6/10 Okay

"The checkin staff and later that evening were a 5. Checkout we were not happy with. My daughter got sick and we asked for 12 checkout for her room only. We didn’t say she was sick. She said 11:30. She didn’t tell anyone as housekeeping came to room at 11:20. We called and again asked for time - she said she can have a “few minutes”. We don’t stay at Quality Inns but travel a lot and have never been told no to a later check if needed it. BTW the parking lot was pretty empty so I don’t think they “needed that one room”. Again the younger girl at checking was great and the gentleman later that night were great. "

Find out more about Southold

Southold B&B information

Number of reviews	1,151
Accommodation	30 B&B
Lowest Price	Rp4.041.410
Highest Price	Rp8.538.393

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. Mill House Inn: 10 rooms. Located 14.4 mi (23.1 km) from the core of Southold. Enjoy the free cooked 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 Croteaux Vineyards. You should put Horton Lane Beach and Osprey's Dominion 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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