20 Best B&B in Southold, NY - Bed and Breakfast from ₩358,737

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. 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.

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

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Our top choices for Southold bed & breakfast

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

1. West Neck Guesthouse

Shelter Island Heights

Allie

₩494,869 total

includes taxes & fees

Sep 1 - Sep 2

2. The Captain Stannard

Westbrook Center

Joseph

₩358,737 total

includes taxes & fees

Sep 20 - Sep 21

3. Harpoon House

Southampton

Kim

₩445,860 total

includes taxes & fees

Sep 1 - Sep 2

4. The Sagaponack

Wainscott

Jane

₩616,869 total

includes taxes & fees

Aug 30 - Aug 31

5. Westbrook Inn B&B

Westbrook Center

Diane

₩455,944 total

includes taxes & fees

Sep 23 - Sep 24

6. The Scranton Seahorse Inn

Madison Center

Krishna

₩575,100 total

includes taxes & fees

Sep 24 - Sep 25

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

7. The Homestead

Madison Center

Sherry

₩387,644 total

includes taxes & fees

Sep 2 - Sep 3

8. The Huntting Inn

Egypt Lane Historic District

James Patrick

₩908,830 total

includes taxes & fees

Sep 23 - Sep 24

9. East Hampton Art House Bed & Breakfast

Clearwater Beach

IVAN

₩1,299,041 total

includes taxes & fees

Sep 8 - Sep 9

Beach nearby, sun loungers, beach umbrellas, beach towels

10. The Hedges Inn

East Hampton

Lauren

₩932,483 total

includes taxes & fees

Sep 21 - Sep 22

11. Mill House Inn

Pantigo Road Historic District

Ronald

₩1,747,211 total

includes taxes & fees

Sep 8 - Sep 9

Traditional Cottage, 2 Bedrooms, Lake View (Pet not allowed) | Desk, laptop workspace, iron/ironing board, WiFi (free)

12. Head of Pond House

Water Mill

Liz

₩3,334,454 total

includes taxes & fees

Sep 9 - Sep 10

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Top Southold Hotel Reviews

The Shoals Suites and Slips

10/10 Excellent

"Beautiful spacious rooms with great rocking chairs on the balcony with a water view. Property was immaculate. Lovely continental breakfast. Great outdoor food truck for a snack and adult beverage!"

Zey Hotel

8/10 Good

"Staff was accommodating and kind. The coffee and tea is a nice touch. Great location and nice common areas. Free parking. The room was a little shoddy, especially the bathroom but products were nice. They really need to dilute the cleaning products though. Way too strong of a smell in the linens and the room. We had to keep the doors open to air it out."

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Absolute gem really cool giant picnic table in the middle of the room, which is great for kids are just getting work done. The staff is absolutely wonderful. The view is gorgeous. If you stay on the backside of the hotel cannot recommend this place enough. What a surprise incredible bargain."

Budget Host East End

8/10 Good

"We came for the pool and enjoyed every minute of a few relaxing days poolside. Lush green grounds provided some shady picnic tables when it was time to get out of the sun. If you are looking for an inexpensive stay not far from the Hamptons or North Fork this is your place. Staff, especially, front desk, very nice, friendly and informative. Rooms had a mini fridge and comfy bed. A/C worked great. Try to get a poolside room. Hotel includes continental breakfast on weekends. Multiple excellent restaurant options nearby on Main Street. We would recommend Olga's for breakfast, offers outdoor/indoor seating. For dinner there is Cliff's Rendezvous steak house. Call and go when they offer their steak special night. Jerry and the Mermaid for seafood, also has outdoor/indoor seating by the water. There is Tweed's where you can try Buffalo. And a few hidden gems with great water views and outdoor seating -Turkuaz (Turkish food ) and Country Farm Kitchen. There is Atlantis Aquarium nearby, that also offers boat tours of the Peconic by day and booze cruises weekend eves. Suffolk Theatre offers well known artists in concert on the weekends. There are at least 4 breweries a short drive away and homemade ice cream at Snowflake and homemade chocolate at North Fork Chocolate & Eatery. Polish Town is nearby if you want Polish food try the Birchwood Restaurant or groceries from the town's deli's."

Find out more about Southold

Southold B&B information

Number of reviews	945
Accommodation	32 B&B
Lowest Price	₩358,737
Highest Price	₩3,334,454

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. 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 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 Mattebella Vineyards. You might put Croteaux Vineyards and McCabe's Beach 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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