20 Best B&B in Southold, NY - Bed and Breakfast from ￥27,374

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. Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower : 1.3 mi (2.1 km) from the downtown core. Enjoy the in-room fireplace and hot tub. The Sagaponack : Situated 12 mi (19.3 km) from the heart of Southold. Harpoon House : 9 rooms. 12.4 mi (19.9 km) from the heart of downtown. Enjoy the bars and unique décor. 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.

Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod.

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Our top choices for Southold bed & breakfast

Vine & Sand

Southold

Judy

￥56,740 total

includes taxes & fees

Mar 18 - Mar 19

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Southold

￥63,810 total

includes taxes & fees

Mar 18 - Mar 19

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Southold

"Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great...

Jessica P.

￥70,264 total

includes taxes & fees

Mar 18 - Mar 19

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Southold

Mark L.

￥63,810 total

includes taxes & fees

Mar 18 - Mar 19

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Southold

￥71,901 total

includes taxes & fees

Mar 30 - Mar 31

Harpoon House

Southampton

Keith

￥27,374 total

includes taxes & fees

Mar 18 - Mar 19

Westbrook Inn B&B

Westbrook Center

Michael

￥33,090 total

includes taxes & fees

Mar 30 - Mar 31

The Captain Stannard

Westbrook Center

John

￥38,017 total

includes taxes & fees

Apr 16 - Apr 17

The Sagaponack

Wainscott

Gina

￥34,455 total

includes taxes & fees

Mar 18 - Mar 19

Graybarn Cottage | Frette Italian sheets, premium bedding, down comforters, pillowtop beds

Mill House Inn

Pantigo Road Historic District

Eliane

￥50,000 total

includes taxes & fees

Mar 22 - Mar 23

Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board

James Pharmacy Bed & Breakfast

Old Saybrook Center

Isolde

￥53,359 total

includes taxes & fees

Apr 16 - Apr 17

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

The Homestead

Madison Center

Anthony

￥49,866 total

includes taxes & fees

Mar 26 - Mar 27

The Huntting Inn

Egypt Lane Historic District

Valerie

￥70,785 total

includes taxes & fees

Mar 18 - Mar 19

Large Room w use of pool/tennis in Spacious home

Sag Harbor

￥129,297 total

includes taxes & fees

Mar 18 - Mar 19

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Top Southold Hotel Reviews

Saybrook Point Resort & Marina

10/10 Excellent

"Our group of 6 girlfriends had an amazing stay at Saybrook Point Resort & Marina. From the moment we arrived, we knew the weekend was going to be very special. The staff was always warm & welcoming. Shoutout to Scott at reception for ensuring a perfect stay! Dinner at Fresh Salt was delicious & the atmosphere was lively. Shuttle into town was a great option. Can’t wait to book another visit!"

Spark by Hilton Guilford

6/10 Okay

"The room was great and staff was friendly. My issue was at checkout. I stayed for a week for work but need to extended for an additional week. My daughter and her car was in the room with me. I paid an additional fee for her car. When I extended my stay, no I did no check out and book a different room, I extended my stay in the same room, they charged me an additional pet fee and another “incidentals” fee. As if I checked out and requested a different room but I didn’t."

Find out more about Southold

Southold B&B information

Number of reviews	1,113
Accommodation	38 B&B
Lowest Price	￥27,374
Highest Price	￥129,297

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, Horton Lane Beach and McCabe's 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. Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower: 1.3 mi (2.1 km) from the downtown core. Enjoy the in-room fireplace and hot tub. The Sagaponack: Situated 12 mi (19.3 km) from the heart of Southold. Harpoon House: 9 rooms. 12.4 mi (19.9 km) from the heart of downtown. Enjoy the bars and unique décor. 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 Croteaux Vineyards and Osprey's Dominion. You might put Horton Lane Beach and Sannino's Bella Vita Vineyard 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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