Southold B&B: Find the Best Bed and Breakfast from CA $225

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.

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Our top choices for Southold bed & breakfast

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

1. Harpoon House

Southampton

Yuliya V

CA $257 total

includes taxes & fees

Nov 19 - Nov 20

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

2. The Sagaponack

Wainscott

Jane

CA $389 total

includes taxes & fees

Nov 15 - Nov 16

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

3. The Captain Stannard

Westbrook Center

Siegfried

CA $367 total

includes taxes & fees

Nov 9 - Nov 10

A deck with a wicker sofa and cushions, surrounded by a white fence and trees.

4. Large Room w use of pool/tennis in Spacious home

Sag Harbor

CA $1,106 total

includes taxes & fees

Nov 9 - Nov 10

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

5. The Huntting Inn

Egypt Lane Historic District

Josie

CA $558 total

includes taxes & fees

Nov 9 - Nov 10

6. The Scranton Seahorse Inn

Madison Center

Tracy

CA $368 total

includes taxes & fees

Nov 10 - Nov 11

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

7. East Hampton Art House Bed & Breakfast

Clearwater Beach

IVAN

CA $730 total

includes taxes & fees

Nov 9 - Nov 10

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

8. Mill House Inn

Pantigo Road Historic District

Rhett

CA $664 total

includes taxes & fees

Nov 10 - Nov 11

A red door with a 'Gone to the Beach' sign, a wicker chair, a table with a plate of food and drinks, and a potted plant.

9. The Homestead

Madison Center

Anita C

CA $348 total

includes taxes & fees

Dec 7 - Dec 8

A round outdoor fire pit with flames, surrounded by wicker furniture and a white cushion.

10. Westbrook Inn B&B

Westbrook Center

Diane

CA $465 total

includes taxes & fees

Nov 10 - Nov 11

A dark-colored SUV parked on a paved surface with a wooded area in the background.

11. Lux Southampton B&B: Pool, Tennis, Gym & Bikes

Southampton

CA $644 total

includes taxes & fees

Nov 9 - Nov 10

A spacious living room with a large sofa, a coffee table, and a television mounted on the wall.

12. Garden Oasis B&B w/ Pool & Bikes in Southampton

Southampton

CA $1,343 total

includes taxes & fees

Nov 9 - Nov 10

A bedroom with a large bed, two bedside lamps, a nightstand, a potted plant, and two framed pictures on the wall.

13. B&B Near Shinnecock: Pool, Tennis, Beach Access

Southampton

CA $557 total

includes taxes & fees

Nov 9 - Nov 10

A dark blue SUV parked on a paved area with trees in the background.

14. Luxury B&B: Pool, Tennis, Free Local Rides

Southampton

CA $570 total

includes taxes & fees

Nov 9 - Nov 10

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Learn more about Southold

Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip.

See all hotels in Southold

A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.

Top reviews in Southold

The Captain Stannard

Westbrook Center

10/10 Excellent

Our stay was great! My flight got in early, and the innkeeper was very kind to let me check in early. The room was clean, comfortable, and safe. The doors to the inn are locked with a keypad that every traveler has a unique code for safety. The first floor common area has a guestbook, a cabinet full of puzzles and other games, a TV, a kitchenette, and lots of seating. The kitchen has a large refrigerator that guests can access along with coffee, tea, and glassware. They also provide postcards...

Casey

The Scranton Seahorse Inn

Madison Center

10/10 Excellent

Francd

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.

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