20 Best B&B in Southold, NY - Bed and Breakfast from SAR 643

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 downtown core. Harpoon House : 9 rooms. Situated 12.4 mi (19.9 km) from the heart of Southold. Enjoy the bars and unique décor. The Hedges Inn : 12 rooms. 14.4 mi (23.1 km) from the heart of downtown. Enjoy the free cooked breakfast and designer toiletries. The Homestead : 10 rooms. Located 17.8 mi (28.6 km) from the core of Southold. Enjoy the deli and unique décor.

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

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

Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.

1. The Sagaponack

Wainscott

Jane

SAR 982 total

includes taxes & fees

28 Oct - 29 Oct

A dining area with a wooden table, chairs, and a view of greenery through large windows.

2. Carole's Place B & B

East Quogue

carolyn

SAR 643 total

includes taxes & fees

8 Nov - 9 Nov

A living room with a stone fireplace, grey sofas, and a coffee table.

3. The Captain Stannard

Westbrook Center

Siegfried

SAR 887 total

includes taxes & fees

12 Nov - 13 Nov

A staircase with a white railing, a white chandelier, and framed artwork on the walls.

4. Harpoon House

Southampton

Yuliya V

SAR 1,066 total

includes taxes & fees

3 Nov - 4 Nov

A beach chair with a striped cushion and a bag with a floral design.

5. The Hedges Inn

East Hampton

Lauren

SAR 1,590 total

includes taxes & fees

27 Oct - 28 Oct

A beach with a lifeguard tower, sandy dunes, and the ocean.

6. The Huntting Inn

Egypt Lane Historic District

Josie

SAR 1,573 total

includes taxes & fees

8 Nov - 9 Nov

A house with a sloped roof, large windows, and a pathway leading to the entrance.

7. Mill House Inn

Pantigo Road Historic District

Rhett

SAR 1,763 total

includes taxes & fees

27 Oct - 28 Oct

A large, multi-story building with a swimming pool, outdoor seating, and a well-maintained garden.

8. East Hampton Art House Bed & Breakfast

Clearwater Beach

IVAN

SAR 1,940 total

includes taxes & fees

2 Nov - 3 Nov

View all properties

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

Top Southold Hotel Reviews

The Shoals Suites and Slips

10/10 Excellent

"Wonderful stay. Everything was perfect. Front desk people were lovely"

Faraway Sag Harbor

8/10 Good

"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."

The Harbor Front Inn

8/10 Good

"The room was clean and the staff is always wonderful. Parking was a nightmare because of the festival which had nothing to do with the hotel. My only issue is the breakfast , I wish it had a little more so I don’t have to go down the street to get something to eat . Honestly it’s not even an issue we will continue to stay here because it is a very nice hotel"

Frequently asked questions

Searching for B&Bs in Southold?

If you're looking for something a little different than your standard hotel experience, a stay at a bed and breakfast could be a great option for your trip. 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 interact with the owner, and breakfast served on site, B&Bs provide a unique 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 downtown core. Harpoon House: 9 rooms. Situated 12.4 mi (19.9 km) from the heart of Southold. Enjoy the bars and unique décor. The Hedges Inn: 12 rooms. 14.4 mi (23.1 km) from the heart of downtown. Enjoy the free cooked breakfast and designer toiletries. The Homestead: 10 rooms. Located 17.8 mi (28.6 km) from the core of Southold. Enjoy the deli and unique décor.

How many Bed & Breakfasts will I be able to find in Southold?

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

When should I 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 temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Southold is 57 inches.

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 might 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?

Planning your excursions in and around Southold is easier with these transportation options. Fly into East Hampton, NY (HTO), which is located 11.8 mi (18.9 km) away from the heart of the city. You can also search for flights into Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates