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. The Hedges Inn : 12 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.

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

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Our top choices for Southold bed & breakfast

A bedroom with a bed, bedside tables, a lamp, a window, and a door.

1. West Neck Guesthouse

Shelter Island Heights

Allie

฿11,781 total

includes taxes & fees

10 Sept - 11 Sept

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

2. Harpoon House

Southampton

Kim

฿9,163 total

includes taxes & fees

1 Oct - 2 Oct

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

3. The Captain Stannard

Westbrook Center

Deborah

฿8,540 total

includes taxes & fees

10 Sept - 11 Sept

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

4. The Sagaponack

Wainscott

Jane

฿11,187 total

includes taxes & fees

8 Oct - 9 Oct

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

5. Westbrook Inn B&B

Westbrook Center

Diane

฿10,826 total

includes taxes & fees

23 Sept - 24 Sept

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.

6. The Homestead

Madison Center

Sherry

฿9,556 total

includes taxes & fees

23 Sept - 24 Sept

7. The Scranton Seahorse Inn

Madison Center

Vicki

฿13,696 total

includes taxes & fees

23 Sept - 24 Sept

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

฿25,731 total

includes taxes & fees

28 Sept - 29 Sept

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Top Southold Hotel Reviews

Zey Hotel

10/10 Excellent

"Such an amazing hotel to stay for the weekend"

The Hampton Maid

10/10 Excellent

"Our stay at The Hampton Maid was such a great choice. The entire hotel is absolutely charming—you can tell that every corner and every detail has been thoughtfully designed. The front desk staff was wonderful: so friendly, welcoming, and very clear with all the information. We loved the bungalow-style rooms, each with its own deck and parking, which gives you wonderful privacy between rooms. But what truly stole our hearts was the gorgeous, beautifully kept garden—a true green oasis that brings complete peace and lets you fully disconnect from city stress. The room was spotless, and the restaurant was phenomenal—we had breakfast there, and it was spectacular. On top of that, getting a pass to 7 local beaches for just $5 is an incredible perk. You really couldn't ask for more! It’s one of those places where you haven't even left yet, and you're already planning your return. Can't wait to go back!"

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Welcoming, helpful, friendly, professional front desk staff. My room was impeccably clean and tidy. The property is centrally-located with ease of accessibility to main roads and major highways, yet far enough off Boston Post Road to ensure a quiet, peaceful and restful stay. Overall, an outstanding, no-frills property! I look forward to staying here once again!"

Saybrook Point Resort & Marina

10/10 Excellent

"Old Saybrook never disappoints. The rooms have been remodel Edinburgh the last six months but the resort has managed to retain its old world chatm. Eventhough there were three weddings at the property during our visit, the staff were attentive to us and we weren't as re remained their only guests. We will visit again."

Find out more about Southold

Southold B&B information

Number of reviews	739
Accommodation	32 B&B
Lowest Price	฿8,540
Highest Price	฿42,615

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 Hedges Inn: 12 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 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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