Search B&B in Southold

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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, (123)
"Beautiful for a quiet weekend getaway "
The price is NT$6,068
NT$8,063 total
includes taxes & fees
Dec 5 - Dec 6
The Sagaponack
Harpoon House
Porch
Harpoon House
3.0 star property
8.2 out of 10, Very Good, (109)
"The place and the room were great and extremely well equipped. This was an independent stay, but staff was very efficient and friendly in checking us in."
The price is NT$5,561
NT$6,347 total
includes taxes & fees
Nov 27 - Nov 28
Harpoon House
The Captain Stannard B&B Country Inn
Front of property
The Captain Stannard B&B Country Inn
3.0 star property
9.6 out of 10, Exceptional, (213)
"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$7,644
NT$8,484 total
includes taxes & fees
Dec 5 - Dec 6
The Captain Stannard B&B Country 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!"
Carole's Place B & B
The Huntting Inn
Exterior
The Huntting Inn
3.5 star property
8.6 out of 10, Excellent, (86)
"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$11,635
NT$13,603 total
includes taxes & fees
Dec 5 - Dec 6
The Huntting Inn
Mill House Inn
Front of property - evening/night
Mill House Inn
5.0 star property
8.8 out of 10, Excellent, (58)
"Lovely building. Our room was great. Staff were very nice and accommodating. We would definitely return."
The price is NT$8,124
NT$10,199 total
includes taxes & fees
Dec 3 - Dec 4
Mill House Inn
Vine & Sand
Interior entrance
Vine & Sand
3.0 star property
10.0 out of 10, Exceptional, (6)
"My husband and I escaped to Long Island for a beautiful fall weekend and thoroughly enjoyed our stay at Vine + Sand. The hosts were very friendly and helpful with restaurant reservations and offered great tips for local activities. The accommodations were eco-friendly, modern and super comfortable and the breakfast in the morning offered delicious pastries and other homemade foods from local bakeries and markets which were a great touch. The location was private yet close enough to get to town...
Vine & Sand
The Scranton Seahorse Inn
Staircase
The Scranton Seahorse Inn
3.0 star property
9.0 out of 10, Wonderful, (233)
"This B and B Inn was a top tier find! The room was large, bed soft, pillows perfect! Michael our host was and extraordinary cook. The frittata was tasty and fluffy. He was also a truly friendly gentleman. "
The price is NT$6,879
NT$7,636 total
includes taxes & fees
Dec 6 - Dec 7
The Scranton Seahorse 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, (70)
"Great area , Great people,"
The price is NT$9,139
NT$10,145 total
includes taxes & fees
Dec 23 - Dec 24
The Homestead
Westbrook Inn B&B
Terrace/patio
Westbrook Inn B&B
3.0 star property
10.0 out of 10, Exceptional, (140)
"It was wonderful "
The price is NT$6,996
NT$7,765 total
includes taxes & fees
Nov 24 - Nov 25
Westbrook Inn B&B
434 on Main
Reception hall
434 on Main
4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
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$9,822
NT$14,801 total
includes taxes & fees
Dec 3 - Dec 4
James Pharmacy Bed & 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
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
Stirling House Bed & Breakfast
Dock
Stirling House Bed & Breakfast
3.0 star property
9.8 out of 10, Exceptional, (22)
"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."
The price is NT$8,203
NT$9,362 total
includes taxes & fees
Dec 17 - Dec 18
Stirling House Bed & Breakfast
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, (60)
"Beautiful grounds, pool and hot tub! Beautiful breakfast!"
The price is NT$13,750
NT$15,692 total
includes taxes & fees
Nov 25 - Nov 26
East Hampton Art House Bed & Breakfast
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
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
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, (262)
"smooth check in, very clean place, via text comunication extremely effective, we also loved the small kitchen in the room, ideal for some coffee making or warming ubp a bite we simply loved the place."
The price is NT$4,103
NT$5,389 total
includes taxes & fees
Dec 3 - Dec 4
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (206)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
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. Harpoon House: 9 rooms. Situated 12.4 mi (19.9 km) from the heart of Southold. Enjoy the bars and unique décor. 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. Mill House Inn: 10 rooms. Located 14.3 mi (23.1 km) from the core of Southold. Enjoy the free cooked breakfast and designer toiletries.
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 Corey Creek Winery 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.