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Check prices for these dates

Next weekend
9 Jan - 11 Jan
In two weeks
16 Jan - 18 Jan
In one month
30 Jan - 1 Feb
In two months
27 Feb - 1 Mar

Our top choices for Southold bed & breakfast

Interior entrance
Vine & Sand

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
Vine & Sand
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

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)
"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 HK$2,603
HK$3,374 total
includes taxes & fees
4 Jan - 5 Jan 2026
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

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)
"Great experience. Wonderful hosts. "
United States
Mark L.
The price is HK$2,358
HK$3,058 total
includes taxes & fees
4 Jan - 5 Jan 2026
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Exterior
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

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Southold
The price is HK$2,440
HK$3,036 total
includes taxes & fees
1 Jan - 2 Jan 2026
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 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

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Southold
The price is HK$2,603
HK$3,374 total
includes taxes & fees
4 Jan - 5 Jan 2026
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

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (259)
"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
Terrace/patio
Westbrook Inn B&B

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (178)
"Our stay was amazing! All the staff were so accommodating and kind. The inn has a rustic charm and was so festive for the holidays! Rooms are a good size, clean, and have everything you need. The breakfast was delicious and they even had free tea/coffee/cookies for all guests to enjoy :) "
United States
Chewon
The price is HK$1,672
HK$1,856 total
includes taxes & fees
30 Dec - 31 Dec
Westbrook Inn B&B
Exterior
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (216)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is HK$1,189
HK$1,670 total
includes taxes & fees
8 Jan - 9 Jan 2026
The Sagaponack
Seasonal outdoor pool
Head of Pond House

Head of Pond House

Head of Pond House
3.0 star property
Water Mill
10.0 out of 10, Exceptional, (3)
"Beautiful place with a very kind host. Highly recommend this place!"
United States
Michèle
The price is HK$3,847
HK$4,395 total
includes taxes & fees
5 Jan - 6 Jan 2026
Head of Pond House
Front of property – evening/night
Mill House Inn

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (75)
"the rooms are outdated and the front desk staff was overbearing the location is great but it’s noisy the breakfast was awesome as was the chef "
United States
Sharon
The price is HK$3,691
HK$4,639 total
includes taxes & fees
31 Dec - 1 Jan 2026
Mill House Inn
Beach/ocean view
Stirling House Bed & Breakfast

Stirling House Bed & Breakfast

Stirling House Bed & Breakfast
3.0 star property
Greenport
9.8 out of 10, Exceptional, (24)
"Our stay was only 2 nights but felt like 5. Well rested 3 days. Would return in a Heart Beat. Clay was awesome and the breakfasts were over the top !"
United States
Adam
The price is HK$2,602
HK$2,973 total
includes taxes & fees
23 Jan - 24 Jan 2026
Stirling House Bed & Breakfast
Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds
The Homestead

The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (91)
"Beautiful property- wonderful staff- clean, comfortable and relaxed feeling with a lovely breakfast 😄"
United States
Anthony
The price is HK$2,186
HK$2,426 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Homestead
Porch
Harpoon House

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (148)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
United States
Karissa
Harpoon House
Garden
The Huntting Inn

The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (104)
"Staff and management was very welcoming!"
United States
Sanailer
The price is HK$2,973
HK$3,474 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Huntting Inn
Outdoor dining
Large Room w use of pool/tennis in Spacious home

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 HK$4,441
HK$6,406 total
includes taxes & fees
30 Dec - 31 Dec
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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Top Southold Hotel Reviews

Residence Inn by Marriott New York Long Island East End

Residence Inn by Marriott New York Long Island East End

10/10 Excellent
"Excellent "
Meiqiong 1-night trip
Posted 3 days ago
Residence Inn by Marriott New York Long Island East End

Find out more about Southold

Southold B&B information

Number of reviews
1,103
Accommodation
38 B&B
Lowest Price
HK$1,670
Highest Price
HK$6,406

Frequently asked questions

Searching for B&Bs in Southold?
If you're interested in something a little more offbeat than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your getaway. If you'd like to spend some time by the water during your time in Southold, McCabe's Beach and Horton Lane 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 socialise with other guests and of course a full breakfast to start the day, B&Bs offer a truly one-of-a-kind 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 city centre. The Captain Stannard: 11 rooms. Situated 15.2 mi (24.4 km) from the heart of Southold. Enjoy the private garden and unique decor. Harpoon House: 9 rooms. 12.4 mi (19.9 km) from the city centre. Enjoy the bars and unique decor. 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 centre.
How many bed & breakfasts will I find in Southold?
Expedia has 5 B&Bs for your time in Southold.
When is the best time to 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 temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Southold is 1452 mm.
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 should put Croteaux Vineyards and Custer Institute and Observatory on your list if you want to see more of the area.
How can I get to and around Southold?
Mapping out your trip in and around Southold is easy with these transportation options. Fly into East Hampton, NY (HTO), which is located 11.8 mi (18.9 km) from the heart of the city. Otherwise, you can search for flights to Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away. If you'd like to venture out around the area, consider renting a car to explore more sights.

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