Southold B&B: Find a Bed and Breakfast 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

includes taxes & fees

8 Apr - 9 Apr

Harpoon House

Southampton

robert

includes taxes & fees

30 Mar - 31 Mar

Westbrook Inn B&B

Westbrook Center

Beth

includes taxes & fees

31 Mar - 1 Apr

Individually decorated, individually furnished, iron/ironing board

James Pharmacy Bed & Breakfast

Old Saybrook Center

Isolde

includes taxes & fees

1 Apr - 2 Apr

The Sagaponack

Wainscott

Gina

includes taxes & fees

12 Apr - 13 Apr

The Captain Stannard

Westbrook Center

GAIL

includes taxes & fees

5 Apr - 6 Apr

Frette Italian sheets, premium bedding, down duvets, pillow-top beds

Mill House Inn

Pantigo Road Historic District

Eliane

includes taxes & fees

31 Mar - 1 Apr

The Homestead

Madison Center

Anthony

includes taxes & fees

29 Mar - 30 Mar

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Top Southold Hotel Reviews

Hyatt Place Long Island East End

10/10 Excellent

"Did not use "

Sound View Greenport

8/10 Good

"Lovely hotel. Amazing location. Gorgeous views. Breakfast was good continental. It rained hard and we had some water leaking in the door from the back deck. Mentioned it to the front desk when we checked out. Could’ve posed a Could’ve posed a slipping hazard.Otherwise, I would’ve given five stars. "

Find out more about Southold

Southold B&B information

Number of reviews	1,117
Accommodation	30 B&B
Lowest Price	S$220
Highest Price	S$681

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 Croteaux Vineyards and Osprey's Dominion. You should put Horton Lane Beach and Sannino's Bella Vita Vineyard 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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