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Check prices for these dates

Next weekend
Mar 14 - Mar 16
In two weeks
Mar 21 - Mar 23
In one month
Apr 4 - Apr 6
In two months
May 2 - May 4

Compare 25 B&B in Southold with updated reviews, rates, and availability.

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (138)
"Great place to stay. Great location. Clean and the room has everything you would need. Will definitely be back!"
The price is NT$5,116
NT$7,157 total
includes taxes & fees
Mar 24 - Mar 25
The Sagaponack
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (67)
"What a lovely space and wonderful thoughtful staff! Absolutely loved everything about it, and the breakfast was beyond excellence! Hats off to the chef you can tell she cooked with ❤️ love. Highly Recommend you experience it for yourself. "
The price is NT$8,228
NT$10,340 total
includes taxes & fees
Mar 9 - Mar 10
Mill House Inn
The Scranton Seahorse Inn
Staircase

The Scranton Seahorse Inn

3.0 star property
9.0 out of 10, Wonderful, (235)
"This was a one night stay. The property is an older house in the city center. We were here to help a friend celebrate a birthday. The B&B was very close to the party making it easy to come and go. The room was small but comfortable. The bed was very comfortable. Breakfast was fantastic. "
The price is NT$8,419
NT$9,345 total
includes taxes & fees
Apr 1 - Apr 2
The Scranton Seahorse Inn
Carole's Place B & B
Property grounds

Carole's Place B & B

3.0 star property
9.6 out of 10, Exceptional, (67)
"We stayed with Carole for two nights, and we absolutely loved her place! The location was perfect for us—central and convenient. From the moment we arrived, we felt right at home. She has created such a warm and cozy space, and her hospitality made all the difference. We truly appreciated her kindness and how welcoming she was. Without a doubt, we’ll be staying with her again the next time we visit Long Island!"
The price is NT$4,919
NT$5,620 total
includes taxes & fees
Apr 3 - Apr 4
Carole's Place B & B
The Homestead
Room, 1 King Bed, Patio, Ground Floor (7) | Egyptian cotton sheets, premium bedding, down comforters

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (77)
"Charming in every aspect. Highly recommend, Hosts are wonderful people."
The price is NT$8,301
NT$9,214 total
includes taxes & fees
Apr 1 - Apr 2
The Homestead
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (145)
"Meri and her staff were exceptionally welcoming, providing us with a wonderful B&B experience. We will return to the Westbrook Inn!"
The price is NT$6,101
NT$6,772 total
includes taxes & fees
Mar 9 - Mar 10
Westbrook Inn B&B
The Huntting Inn
Exterior

The Huntting Inn

3.5 star property
8.6 out of 10, Excellent, (87)
"One of the very few options in East Hampton that offered a one night stay, most have a 2-night minimum. An old, charming inn that was very welcoming and clean. Our king bed room was spacious enough and decorated nicely. The bathroom was very clean and modernized. We did have to walk up a flight of stairs with our luggage which wasn’t difficult for us but may be for some."
The price is NT$16,711
NT$19,421 total
includes taxes & fees
Apr 6 - Apr 7
The Huntting Inn
Harpoon House
Porch

Harpoon House

3.0 star property
8.2 out of 10, Very Good, (113)
"Our stay was spectacular!"
The price is NT$5,739
NT$6,557 total
includes taxes & fees
Mar 13 - Mar 14
Harpoon House
The Captain Stannard B&B Country Inn
Standard Room, 1 Bedroom, Private Bathroom | Free WiFi, bed sheets

The Captain Stannard B&B Country Inn

3.0 star property
9.6 out of 10, Exceptional, (214)
"We had a wonderful time and the owner was great. We had a fun time talking about history of both inn’s. Look forward to returning and doing more next time"
The price is NT$4,666
NT$5,179 total
includes taxes & fees
Mar 10 - Mar 11
The Captain Stannard B&B Country Inn
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
West Neck Guesthouse
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very Good, (32)
"Very convenient location next to Cresent Beach and Leon 1909 restaurant which is fantastic! "
West Neck Guesthouse
The Hedges Inn
Room One: Large Queen Guestroom | Egyptian cotton sheets, premium bedding, in-room safe

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (68)
"Super friendly staff, very accommodating! We can’t wait to return. "
The Hedges Inn
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (61)
"What a beautiful, quiet, peaceful place to stay, even in the dead of winter. The home itself is modern, welcoming, bright, everything you could dream of. The hosts are very active and successful artists who all but gave us a private master class in how their work is imagined and created. I don’t know when we’ve had a more delightful weekend. The walks to the beach were lovely, too. "
The price is NT$13,853
NT$15,827 total
includes taxes & fees
Apr 3 - Apr 4
East Hampton Art House Bed & Breakfast
Arbor View House B&B
Exterior

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (13)
"This house was old but beautiful and decorated nicely inside. "
Arbor View House B&B
Stirling House Bed & Breakfast
Dock

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (23)
"Very comfortable king size bed. Excellent gourmet breakfast, discreet host. Older house, but all the comforts. Absolutely every need provided for. "
The price is NT$11,021
NT$12,592 total
includes taxes & fees
Mar 11 - Mar 12
Stirling House Bed & Breakfast
James Pharmacy Bed & Breakfast
Garden

James Pharmacy Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (14)
"We loved staying in the historic pharmacy. We stayed in the Ann Petry room and it is well appointed, clean and charming. The property sits on the town's main street and is very walkable to shopping and dining. We look forward to our next stay. "
The price is NT$9,947
NT$14,991 total
includes taxes & fees
Apr 1 - Apr 2
James Pharmacy Bed & Breakfast
Vine & Sand
Interior entrance

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (7)
"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. "
Vine & Sand
The Baker House 1650
Indoor pool, seasonal outdoor pool, sun loungers

The Baker House 1650

4.5 star property
9.4 out of 10, Exceptional, (33)
"Absolutely best place to stay in East Hampton! Charming B&B with incredible staff. "
The Baker House 1650
The Farmhouse Bed and Breakfast
Garden

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (10)
"Lovely B&B run by a lovely couple"
The Farmhouse Bed and Breakfast
Harbor Knoll Bed & Breakfast
Living area

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (9)
"We stayed here for our mini moon and couldn't have asked for a better weekend! We loved hanging out at the inn and getting to know Leueen and the other guests. The inn is walking distance to the main streets and the train. Will definitely visit again!"
Harbor Knoll Bed & Breakfast
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Southold

Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (275)
"Great cozy place"
The price is NT$4,321
NT$5,649 total
includes taxes & fees
Mar 9 - Mar 10
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
The price is NT$5,682
NT$7,916 total
includes taxes & fees
Mar 30 - Mar 31
Cliffside Resort Condominiums
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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 your ideal vacation to Southold includes spending lots of time outside, Horton Point Park is a good spot to enjoy the scenery.
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: The Sagaponack: 12 mi (19.3 km) from the heart of Southold. Enjoy the outdoor pool and free beach shuttle. Harpoon House: 9 rooms. 12.4 mi (19.9 km) from the downtown core. Enjoy the bars and unique décor. Mill House Inn: 10 rooms. Situated 14.3 mi (23.1 km) from the heart of Southold. Enjoy the free cooked breakfast and designer toiletries. East Hampton Art House Bed & Breakfast: 2 rooms. 13.9 mi (22.3 km) from the heart of downtown. Enjoy the free full breakfast and fitness center. The Captain Stannard B&B Country Inn: 11 rooms. Located 15.2 mi (24.4 km) from the core of Southold.
How many Bed & Breakfasts will I be able to find in Southold?
Expedia has 6 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 The Old Field Vineyards. You might put Croteaux Vineyards and Corey Creek Winery 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.