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 bar/lounge.

Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Southold bed & breakfast

The Captain Stannard

Westbrook Center

GAIL

Rp4.637.351 total

includes taxes & fees

18 Jun - 19 Jun

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

West Neck Guesthouse

Shelter Island Heights

Leslie

Rp4.466.786 total

includes taxes & fees

22 Jun - 23 Jun

The Sagaponack

Wainscott

Michael

Rp11.900.947 total

includes taxes & fees

30 Jun - 1 Jul

Westbrook Inn B&B

Westbrook Center

Ashley

Rp6.399.381 total

includes taxes & fees

28 Jun - 29 Jun

The Scranton Seahorse Inn

Madison Center

Brian

Rp7.017.908 total

includes taxes & fees

16 Jun - 17 Jun

Harpoon House

Southampton

"Hotel staff were more than a accommodating, the rooms were unique ,warm and welcoming, Voss waters and expresso in the room . Bedding was marvelous and the bright walk-in glass showers were clean and spacious. The hotel is Steps away from delicious food options while youe neighborhood Starbucks and CVS around the corner. Definitely would stay again ! Amazing place. Full of charm you would expect from a 400 year old property."

VINCENT M

Rp9.062.087 total

includes taxes & fees

16 Jul - 17 Jul

Mill House Inn

Pantigo Road Historic District

Rhett

Rp17.844.283 total

includes taxes & fees

29 Jun - 30 Jun

The Huntting Inn

Egypt Lane Historic District

EDUARD

Rp12.471.459 total

includes taxes & fees

6 Jul - 7 Jul

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Southold Hotel Reviews

Saybrook Point Resort & Marina

10/10 Excellent

"We had a lovely stay! Loved the room decor. Very calm and relaxing.. looking forward to Returning!"

Water's Edge Resort & Spa

8/10 Good

"The resort was very nice and well maintained. I would say the staff wasn't that great. I've much better experiences. I enjoyed my massage and spa. The only complaint I have is that at a room near mine room was very loud and woke me up at 11:30. I couldn't get a response from dialing 0 and I tried 5x. When I brought it to the attention of the front desk clerk she really didn't seem to care much."

Find out more about Southold

Southold B&B information

Number of reviews	1,182
Accommodation	32 B&B
Lowest Price	Rp4.466.786
Highest Price	Rp17.844.283

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 bar/lounge.

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 The Old Field Vineyards. You should put Horton Point Park 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.

Explore a world of travel with Expedia

More ways to book

Book B&B in Southold on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates