Search B&B in Southold

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
13 Mar - 15 Mar
In two weeks
20 Mar - 22 Mar
In one month
3 Apr - 5 Apr
In two months
1 May - 3 May

Our top choices for Southold bed & breakfast

Interior

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful stay"
United States
Judy
Vine & Sand
Interior

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

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Southold
The price is AED 1,153
AED 1,498 total
includes taxes & fees
8 Mar - 9 Mar
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Interior

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

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Southold
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Jessica P.
The price is AED 1,269
AED 1,647 total
includes taxes & fees
8 Mar - 9 Mar
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Interior

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

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Southold
10.0 out of 10, Exceptional, (1 review)
"Great experience. Wonderful hosts. "
United States
Mark L.
The price is AED 1,153
AED 1,498 total
includes taxes & fees
8 Mar - 9 Mar
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Interior

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

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Southold
The price is AED 1,269
AED 1,647 total
includes taxes & fees
8 Mar - 9 Mar
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
IPod dock, MP3 dock

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (260 reviews)
"The Inn and staff were warm and welcoming, the facility exceptionally clean. Breakfast exceeded my expectations for a continental breakfast! Would absolutely stay again! "
United States
Lisa
The Captain Stannard
Fireplace

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (179 reviews)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is AED 703
AED 781 total
includes taxes & fees
19 Mar - 20 Mar
Westbrook Inn B&B
Interior detail

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very Good, (149 reviews)
"Great spot!"
United States
Keith
Harpoon House
Property entrance

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (226 reviews)
"The property and room was clean, easily accessible, and staff were very friendly. We would stay here again!"
United States
Daren
The price is AED 590
AED 802 total
includes taxes & fees
8 Mar - 9 Mar
The Sagaponack
Graybarn Cottage | Frette Italian sheets, premium bedding, down comforters, pillowtop beds

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (81 reviews)
"Great place to stay. Very walkable, lovely room and comfortable bed. "
Australia
Alex
The price is AED 918
AED 1,154 total
includes taxes & fees
8 Mar - 9 Mar
Mill House Inn
Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23 reviews)
"Cute B&B, very nice room, check-in worked well"
United States
Isolde
The price is AED 1,110
AED 1,232 total
includes taxes & fees
1 Apr - 2 Apr
James Pharmacy Bed & Breakfast
Beach nearby

The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (105 reviews)
"Inn has been newly renovated. Room was spotless. Staff were wonderful. Had an excellent stay. Highly recommend! "
United States
Valerie
The price is AED 1,315
AED 1,539 total
includes taxes & fees
23 Mar - 24 Mar
The Huntting Inn
Room, 1 King Bed, Patio, Ground Floor (2) | Terrace/patio

The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (91 reviews)
"Beautiful property- wonderful staff- clean, comfortable and relaxed feeling with a lovely breakfast 😄"
United States
Anthony
The price is AED 1,033
AED 1,147 total
includes taxes & fees
8 Mar - 9 Mar
The Homestead
Terrace/patio

Large Room w use of pool/tennis in Spacious home

Large Room w use of pool/tennis in Spacious home
Sag Harbor
The price is AED 2,099
AED 2,986 total
includes taxes & fees
7 Mar - 8 Mar
Large Room w use of pool/tennis in Spacious home
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.
View all properties

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southold Hotel Reviews

Holiday Inn Express Hotel & Suites Long Island-East End by IHG

Holiday Inn Express Hotel & Suites Long Island-East End by IHG

2/10 Terrible
"We stayed on the property from February 19 to the 22nd. We were across from people who were continuously loud all night till two 3 AM in the morning partying I contacted Security and the front desk and they didn't handle it very well. I ended up having a confrontation with these people that stayed across the hallway from us she threatened my life. Wanted to beat me up and made it very uncomfortable to be at that hotel. I want to be reimbursed for my stay that every night stunk I wanted to stay longer, but I had to go to a different hotel because I was kind of worried that I was gonna be followed from these people that were not handled properly from the staff at Holiday Inn express in Riverhead Long Island. "
Jeanine 3-night trip
Posted 8 hours ago
Holiday Inn Express Hotel & Suites Long Island-East End by IHG

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. 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. James Pharmacy Bed & Breakfast: 3 rooms. 15.5 mi (25 km) from the heart of downtown. Enjoy the local cuisine 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 the lobby and bar/lounge.
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 The Old Field Vineyards and Croteaux Vineyards. You might put Horton Lane Beach and Osprey's Dominion 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.

Explore a world of travel with Expedia