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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 39 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, (145)
"Sara at the front desk was helpful. I had a cottage and it was noisy. I could hear the persons television next door and the cars from the street all night. There was snacks at night. The breakfast was just continental. "
The price is AED 673
AED 958 total
includes taxes & fees
8 Apr - 9 Apr
The Sagaponack
The Captain Stannard
Standard Room, 1 Bedroom, Private Bathroom | Free WiFi, bed sheets

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (217)
"Clean, classic, charming seaside New England inn. Unique in that it isn’t really staffed in the traditional sense but provided much more than we expected - 24 hour guest pantry, beautiful common spaces to relax, fresh cookies upon arrival, and basic breakfast. This will be our new go-to when we’re in the area. "
The price is AED 615
AED 682 total
includes taxes & fees
8 Apr - 9 Apr
The Captain Stannard
Harpoon House
Porch

Harpoon House

3.0 star property
8.2 out of 10, Very Good, (115)
"Place was great! Love the area and place was also very clean and quiet. Great stay and would definitely come back."
The price is AED 1,202
AED 1,373 total
includes taxes & fees
10 Apr - 11 Apr
Harpoon House
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 AED 496
AED 567 total
includes taxes & fees
8 Apr - 9 Apr
Carole's Place B & B
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (68)
"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 AED 1,194
AED 1,500 total
includes taxes & fees
8 Apr - 9 Apr
Mill House Inn
The Scranton Seahorse Inn
Staircase

The Scranton Seahorse Inn

3.0 star property
9.0 out of 10, Wonderful, (236)
"Amazing and too short. Loveliest little B&B with one of the best breakfasts I've ever had. Incredibly clean with updated bathroom(s). So quiet, even though almost full. Will be going back, regularly!"
The price is AED 943
AED 1,047 total
includes taxes & fees
21 Apr - 22 Apr
The Scranton Seahorse Inn
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (148)
"It is beautiful and comfortable. The breakfast was great. And the bed was extremely comfortable."
The price is AED 680
AED 755 total
includes taxes & fees
8 Apr - 9 Apr
Westbrook Inn B&B
The 1708 House
Exterior

The 1708 House

3.0 star property
10.0 out of 10, Exceptional, (1)
The price is AED 1,093
AED 1,276 total
includes taxes & fees
26 Apr - 27 Apr
The 1708 House
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 AED 1,495
AED 1,744 total
includes taxes & fees
4 May - 5 May
The Huntting Inn
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 AED 930
AED 1,032 total
includes taxes & fees
20 Apr - 21 Apr
The Homestead
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
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 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 AED 1,552
AED 1,773 total
includes taxes & fees
8 Apr - 9 Apr
East Hampton Art House Bed & Breakfast
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
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 AED 1,230
AED 1,405 total
includes taxes & fees
8 Apr - 9 Apr
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 AED 1,110
AED 1,673 total
includes taxes & fees
8 Apr - 9 Apr
James Pharmacy 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
Historical Bed and breakfast<br>
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Historical Bed and breakfast<br>

8.6 out of 10, Excellent, (4)
"Very great house , Owner was amazing and was very easy to contact and gave us early check in . Would definitely do it agian"
Historical Bed and breakfast<br>
Large Room w use of pool/tennis in Spacious home
Outdoor dining

Large Room w use of pool/tennis in Spacious home

The price is AED 826
AED 1,339 total
includes taxes & fees
8 Apr - 9 Apr
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.
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Other property types in Southold

North Fork 7 Bedroom Farmhouse Escape
Beach nearby

North Fork 7 Bedroom Farmhouse Escape

3.0 star property
9.4 out of 10, Exceptional, (3)
"We were in town for a wedding with small children in tow- the house was perfectly located for us to get to wedding events in under 10 minutes but do be aware that it’s on a busy road. The house is set back so there wasn’t too much traffic noise, especially with the window AC units going. You could walk to the beach, but be aware that it’s down the busy road as someone else mentioned. It wasn’t luxurious, but everything was clean and comfortable. I appreciated that towels and linens were provided...
North Fork 7 Bedroom Farmhouse Escape
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (282)
"2nd loft bedroom/bath was especially nice"
The price is AED 484
AED 633 total
includes taxes & fees
8 Apr - 9 Apr
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 AED 529
AED 764 total
includes taxes & fees
30 Apr - 1 May
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: 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. The Captain Stannard: 11 rooms. Situated 15.2 mi (24.4 km) from the heart of Southold. Mill House Inn: 10 rooms. 14.3 mi (23.1 km) from the heart of downtown. Enjoy the free cooked breakfast and designer toiletries. East Hampton Art House Bed & Breakfast: 2 rooms. Located 13.9 mi (22.3 km) from the core of Southold. Enjoy the free full breakfast and fitness center.
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 Corey Creek Winery 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.