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Compare 39 B&B in Southold with updated reviews, rates, and availability.

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (149)
"Great experience at a great resort. We loved our cottage and will be back!"
The price is AED 820
AED 1,125 total
includes taxes & fees
7 May - 8 May
The Sagaponack

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (221)
"Wonderful welcome and impeccable property. We will plan to go again!"
The price is AED 723
AED 803 total
includes taxes & fees
7 May - 8 May
The Captain Stannard

Harpoon House

3.0 star property
8.2 out of 10, Very Good, (116)
"Our stay was spectacular!"
The price is AED 1,355
AED 1,548 total
includes taxes & fees
7 May - 8 May
Harpoon House

Carole's Place B & B

3.0 star property
9.6 out of 10, Exceptional, (69)
"Great location and excellent breakfast!"
Carole's Place B & B

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (68)
"Great experience at a wonderful property!"
The price is AED 1,377
AED 1,731 total
includes taxes & fees
8 May - 9 May
Mill House Inn

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (150)
"It is beautiful and comfortable. The breakfast was great. And the bed was extremely comfortable."
The price is AED 711
AED 789 total
includes taxes & fees
7 May - 8 May
Westbrook Inn B&B

The 1708 House

3.0 star property
10.0 out of 10, Exceptional, (2)
"We absolutely loved our stay here. The house is stunning, the service is fabulous. The best bed ever to sleep in! Great location and a fabulous breakfast. Thank you. "
The 1708 House

The Huntting Inn

3.5 star property
8.8 out of 10, Excellent, (88)
"Very reasonably priced, clean, friendly, but basic."
The price is AED 1,674
AED 1,949 total
includes taxes & fees
19 May - 20 May
The Huntting Inn

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (77)
"Wonderful rooms, exceptional staff, and convenient location"
The price is AED 1,136
AED 1,261 total
includes taxes & fees
19 May - 20 May
The Homestead

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! "
The price is AED 703
AED 803 total
includes taxes & fees
22 May - 23 May
West Neck Guesthouse

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (7)
"Bedding, linen breakfasts "
Vine & Sand

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (68)
"Absolutely fabulous homely and beautifully decorated Conveniently located between downtown and the beach so easy to walk"
The Hedges Inn

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (61)
"The hosts were really nice and the breakfast is excellent!"
The price is AED 1,528
AED 1,746 total
includes taxes & fees
12 May - 13 May
East Hampton Art House Bed & Breakfast

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main

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. "
Stirling House Bed & Breakfast

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
The price is AED 1,110
AED 1,673 total
includes taxes & fees
7 May - 8 May
James Pharmacy Bed & Breakfast

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (13)
"Two mid age couples just had a good and relaxing time with great hospitality. "
Arbor View House B&B

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>

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (9)
"Charming bed and breakfast in a great location right on the water…perfect for a romantic getaway!"
Harbor Knoll Bed & Breakfast

Large Room w use of pool/tennis in Spacious home

The price is AED 1,084
AED 1,679 total
includes taxes & fees
7 May - 8 May
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

3.0 star property
9.4 out of 10, Exceptional, (3)
"Nice property, extremely helpful Owner. Great kitchen"
North Fork 7 Bedroom Farmhouse Escape

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (283)
"Love the ocean view from the balcony"
The price is AED 565
AED 725 total
includes taxes & fees
7 May - 8 May
Windward Shores Ocean Resort

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (212)
"Very beautiful location and the room unforgettable ocean view will definitely come back"
The price is AED 638
AED 889 total
includes taxes & fees
7 May - 8 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 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.