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Compare 28 B&B in Southold with updated reviews, rates, and availability.

The Wainscott Inn
Front of property
The Wainscott Inn
3.0 star property
8.6 out of 10, Excellent, (94)
"new remodel is very nice"
The price is AED 1,796
AED 2,177 total
includes taxes & fees
23 Jun - 24 Jun
The Wainscott Inn
Captain Stannard B&B Country Inn
Exterior
Captain Stannard B&B Country Inn
3.0 star property
9.6 out of 10, Exceptional, (177)
"We had a wonderful time. The place was so cute and the staff and owners were so helpful and nice. We only stayed 1 night but I wish we stayed longer. We will definitely be back."
The price is AED 731
AED 811 total
includes taxes & fees
20 Jun - 21 Jun
Captain Stannard B&B Country Inn
Carole's Place B & B
Front of property
Carole's Place B & B
3.0 star property
9.4 out of 10, Exceptional, (40)
"I loved my stay here! Carole is lovely and the property is great."
Carole's Place B & B
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Harpoon House
Reception
Harpoon House
3.0 star property
8.2 out of 10, Very Good, (103)
"very friendly host "
The price is AED 1,826
AED 2,074 total
includes taxes & fees
23 Jun - 24 Jun
Harpoon House
The Scranton Seahorse Inn
Front of property
The Scranton Seahorse Inn
3.0 star property
9.0 out of 10, Wonderful, (218)
"The Seashore is a special INN. It is very quaint, inviting and comfortable. I’d return again."
The price is AED 893
AED 974 total
includes taxes & fees
8 Jul - 9 Jul
The Scranton Seahorse Inn
Vine & Sand
Exterior
Vine & Sand
5.0 star property
Vine & Sand
434 on Main
Front of property
434 on Main
4.0 star property
10.0 out of 10, Exceptional, (34)
"Great hosts"
434 on Main
East Hampton Art House Bed & Breakfast
Aerial view
East Hampton Art House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (55)
"The hosts were really nice and the breakfast is excellent!"
The price is AED 2,797
AED 3,192 total
includes taxes & fees
20 Jun - 21 Jun
East Hampton Art House Bed & Breakfast
Mill House Inn
Front of property
Mill House Inn
5.0 star property
8.8 out of 10, Excellent, (52)
"Excellent facility and excellent service. Highly recommend. "
The price is AED 2,553
AED 3,205 total
includes taxes & fees
20 Jun - 21 Jun
Mill House Inn
The Homestead
Exterior
The Homestead
3.0 star property
10.0 out of 10, Exceptional, (63)
"Excellent accommodations and Host. "
The price is AED 1,538
AED 1,707 total
includes taxes & fees
20 Jun - 21 Jun
The Homestead
Westbrook Inn B&B
Dock
Westbrook Inn B&B
3.0 star property
10.0 out of 10, Exceptional, (136)
"Always an excellent stay! "
The price is AED 908
AED 990 total
includes taxes & fees
23 Jun - 24 Jun
Westbrook Inn B&B
The Hedges Inn
Front of property
The Hedges Inn
3.5 star property
9.6 out of 10, Exceptional, (66)
"Beautiful location and lovely accommodation."
The Hedges Inn
James Pharmacy Bed & Breakfast
Room
James Pharmacy Bed & Breakfast
4.0 star property
9.6 out of 10, Exceptional, (8)
"Near nice shops and restaurants "
The price is AED 1,431
AED 2,008 total
includes taxes & fees
27 Jun - 28 Jun
James Pharmacy Bed & Breakfast
West Neck Guesthouse
Property grounds
West Neck Guesthouse
3.5 star property
7.6 out of 10, Good, (25)
"The walk to the main house was further than noted. Breakfast was sparse compared to other B&B's."
The price is AED 873
AED 996 total
includes taxes & fees
20 Jun - 21 Jun
West Neck Guesthouse
Stirling House Bed & Breakfast
Beach/ocean view
Stirling House Bed & Breakfast
3.0 star property
9.8 out of 10, Exceptional, (21)
"This was a great place to stay with old word charm. If you are looking for a quiet getaway with a beautiful view of the ocean this is it. The breakfast that we had were much better that what you could get in town. My wife and I can't wait to go back."
Stirling House Bed & Breakfast
Historical Bed and breakfast<br>
Exterior
Historical Bed and breakfast<br>
8.0 out of 10, Very Good, (3)
"Thomas was the best vacation rental host we have ever had. So flexible. So responsive—before and during our stay. Very thoughtful and accommodating—he went the extra mile to make our stay great. He met us when we arrived, showed us around the house, and gave us great recommendations in the area. He brought us a blender and cooler when we asked if he had one. The house is awesome—big and nice yard, amazing pool, fun/interesting details inside, comfortable and nice, big/plenty of room for a big...
Historical Bed and breakfast<br>
Harbor Knoll Bed & Breakfast
Exterior
Harbor Knoll Bed & Breakfast
3.0 star property
9.8 out of 10, Exceptional, (6)
"Beautiful, private oceanfront property right next to all the restaurants in town. "
Harbor Knoll Bed & Breakfast
The Farmhouse Bed and Breakfast
Front of property
The Farmhouse Bed and Breakfast
3.5 star property
10.0 out of 10, Exceptional, (5)
"The Farmhouse was a perfect stay for a relaxing weekend in beautiful surroundings. The Farmhouse is charming and impeccably kept. The hosts are friendly and amazing cooks. Added plus : a destination charger for our Tesla! Definitely recommend!"
The Farmhouse Bed and Breakfast
Arbor View House B&B
Room
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
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
The bedoom
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
Don't see what you're looking for?
See all available properties in Southold
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.

Other property types in Southold

Windward Shores Ocean Resort
Property grounds
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (240)
"Access to the beach. "
The price is AED 1,250
AED 1,507 total
includes taxes & fees
23 Jun - 24 Jun
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Room
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (185)
"Had issue with check in. Nothing sent to phone as stated because of limited cell service in area. Had to go to office to get room and code. They have wrong room and had to go back for correct room. This was frustrating because it was after the check in time, which is later than most properties. The unit was fine, bare bones with decor etc. shower in one bathroom was leaking. I have stayed on property few times. This time was definitely less impressive."
The price is AED 1,196
AED 1,525 total
includes taxes & fees
18 Jul - 19 Jul
Cliffside Resort Condominiums
North Fork Escape Near Wineries, Beaches And Hamptons
Room
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
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.
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 Croteaux Vineyards and Sparkling Pointe. 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.

Recent reviews of Southold hotels
Expedia verified reviews

The Bentley Hotel Southampton

The Bentley Hotel Southampton

5/5 Excellent
"After our hotel cancelled on us last minute, we rerouted to the Bentley Hotel. I’m glad we did. Staff were friendly, room was huge and grounds were well maintained. My family had a great Father’s Day weekend at this hotel. "
A verified traveler from Syosset stayed at The Bentley Hotel Southampton
Posted 2 days ago
The Bentley Hotel Southampton