Southold B&B: Best Bed and Breakfast 2026

Q: 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.

Q: 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.

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. The Huntting Inn : 19 rooms. 14.4 mi (23.1 km) from the city centre. Enjoy the fireplace in reception and on-site dining. 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.

Q: How many bed & breakfasts will I find in Southold?

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

Q: 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.

Q: 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.

Q: 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.

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

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Our top choices for Southold bed & breakfast

1. West Neck Guesthouse

Shelter Island Heights

Allie

includes taxes & fees

4 Aug - 5 Aug

2. The Captain Stannard

Westbrook Center

Jessica

includes taxes & fees

5 Aug - 6 Aug

3. Westbrook Inn B&B

Westbrook Center

Diane

includes taxes & fees

17 Aug - 18 Aug

4. Harpoon House

Southampton

Barbara

includes taxes & fees

5 Aug - 6 Aug

5. The Sagaponack

Wainscott

liliana

includes taxes & fees

9 Aug - 10 Aug

6. The Scranton Seahorse Inn

Madison Center

Krishna

includes taxes & fees

5 Aug - 6 Aug

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

7. The Homestead

Madison Center

Mary

includes taxes & fees

31 Aug - 1 Sept

8. Azur East, southampton

Southampton

includes taxes & fees

4 Aug - 5 Aug

9. The Huntting Inn

Egypt Lane Historic District

EDUARD

includes taxes & fees

23 Aug - 24 Aug

10. East Hampton Art House Bed & Breakfast

Clearwater Beach

IVAN

includes taxes & fees

4 Aug - 5 Aug

11. Mill House Inn

Pantigo Road Historic District

Ronald

includes taxes & fees

9 Aug - 10 Aug

Beach nearby, sun-loungers, beach umbrellas, beach towels

12. The Hedges Inn

East Hampton

"A truly wonderful stay. I loved the beautiful design, thoughtful details, and exceptional hospitality. The team made us feel right at home, and every part of the experience, from the delicious breakfast and pet-friendly atmosphere to the beach setup service, was simply lovely. I would happily recommend The Hedges to anyone visiting the Hamptons, and after this experience, I’m even more excited to visit The Colony Palm Beach on a future trip!"

Tina

includes taxes & fees

9 Aug - 10 Aug

13. Pool tennis gym Bikes all included & <2m’s fr/ all

Southampton

includes taxes & fees

4 Aug - 5 Aug

14. Pool Gym Biocharger Tennis Private bath All New BR

Southampton

includes taxes & fees

4 Aug - 5 Aug

15. Free ride to Shinnecock Golf, SH Town or SH beache

Southampton

includes taxes & fees

4 Aug - 5 Aug

16. Home 2 mins. from Shinnecock Golf town SH beaches

Southampton

includes taxes & fees

9 Aug - 10 Aug

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Top Southold Hotel Reviews

Bayview Resort

10/10 Excellent

"Great little gem for a weekend getaway. Staff is nice, rooms are clean and adequate. Nice pool and deck overseeing the water. "

Find out more about Southold

Southold B&B information

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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. The Huntting Inn: 19 rooms. 14.4 mi (23.1 km) from the city centre. Enjoy the fireplace in reception and on-site dining. 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 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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