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 : 12 mi (19.3 km) from the city centre. Harpoon House : 9 rooms. Situated 12.4 mi (19.9 km) from the heart of Southold. Enjoy the bars and unique decor. Mill House Inn : 10 rooms. 14.4 mi (23.1 km) from the city centre. Enjoy the free cooked breakfast and designer toiletries. The Huntting Inn : 19 rooms. Located 14.4 mi (23.1 km) from the core of Southold. Enjoy the fireplace in reception and on-site dining.

A calm lake with a forest in the background during sunset.

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Our top choices for Southold bed & breakfast

Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

Shelter Island Heights

Allie

฿12,069 total

includes taxes & fees

27 Jul - 28 Jul

The Captain Stannard

Westbrook Center

Judith

฿8,749 total

includes taxes & fees

27 Jul - 28 Jul

Westbrook Inn B&B

Westbrook Center

Diane

฿12,073 total

includes taxes & fees

27 Jul - 28 Jul

Harpoon House

Southampton

Barbara

฿17,332 total

includes taxes & fees

2 Aug - 3 Aug

The Sagaponack

Wainscott

liliana

฿24,221 total

includes taxes & fees

3 Aug - 4 Aug

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

The Homestead

Madison Center

Mary

฿11,142 total

includes taxes & fees

27 Jul - 28 Jul

The Scranton Seahorse Inn

Madison Center

Brian

฿13,240 total

includes taxes & fees

27 Jul - 28 Jul

The Huntting Inn

Egypt Lane Historic District

EDUARD

฿22,164 total

includes taxes & fees

23 Aug - 24 Aug

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Top Southold Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Low cost clean older two story motel close to i95 but far enough from the noise. We were there on a weekday in the summer but I doubt it would be noisier on the weekend. One king bed, tiny microwave, under counter fridge could hold all the cooler stuff and freeze the blue ice packs. The lobby has a good selection of books that I was not expecting. There is a tea shop across the street that might have breakfast, and an Italian restaurant that you could also walk to, but instead we drove a couple miles to get all kinds of goodies at mystic market."

The Shoals Suites and Slips

8/10 Good

"Good location, easy trip from Orient Point ferry. Nice property and staff was very good, helpful with recommendations on local places. Beach passes provided. A bit pricey, but comes with the territory and there aren't many places that offer 2 bedroom suites. Bedrooms are on the small side, but comfortable. Overall an enjoyable two night stay."

The Hampton Maid

10/10 Excellent

"Love this place. I am a return visitor. The cottages are modern,, with cottage chic vibe. We stayed in the junior suite. Spacious room and bathroom. Loved our deck and outdoor fireplace. The campus is cute with a nice pool and seating area. The restaurant is so good. A lovely stay. We went with my parents to celebrate mom's birthday and it made for a special weekend."

North Fork Resort

10/10 Excellent

"Stayed here for 1 night and want to come back! Love that it’s dog friendly and also so close to greenport village. The only thing was that the bathroom smelled very mildewy when we woke up in the morning. There was a vent fan but there was no switch that turned it on. Aside from that the unit was great. We loved the fire pit, and I wasn't expecting a standalone tub. The dishes and glassware were also very nice. There’s even a dishwasher built into the counter. We will definitely be back!"

Find out more about Southold

Southold B&B information

Number of reviews	988
Accommodation	32 B&B
Lowest Price	฿8,749
Highest Price	฿48,453

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, McCabe's Beach and Horton Lane 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: 12 mi (19.3 km) from the city centre. Harpoon House: 9 rooms. Situated 12.4 mi (19.9 km) from the heart of Southold. Enjoy the bars and unique decor. Mill House Inn: 10 rooms. 14.4 mi (23.1 km) from the city centre. Enjoy the free cooked breakfast and designer toiletries. The Huntting Inn: 19 rooms. Located 14.4 mi (23.1 km) from the core of Southold. Enjoy the fireplace in reception and on-site dining.

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 Sannino's Bella Vita Vineyard and The Old Field Vineyards 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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