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Check prices for these dates

Next weekend
20 Feb - 22 Feb
In two weeks
27 Feb - 1 Mar
In one month
13 Mar - 15 Mar
In two months
10 Apr - 12 Apr

Our top choices for Southold bed & breakfast

Interior

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful stay"
United States
Judy
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
Southold
10.0 out of 10, Exceptional, (1 review)
"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$2,782
HK$3,634 total
includes taxes & fees
15 Feb - 16 Feb
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
Southold
10.0 out of 10, Exceptional, (1 review)
"Great experience. Wonderful hosts. "
United States
Mark L.
The price is HK$2,536
HK$3,255 total
includes taxes & fees
16 Feb - 17 Feb
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Interior

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$2,536
HK$3,317 total
includes taxes & fees
15 Feb - 16 Feb
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
Southold
The price is HK$2,782
HK$3,634 total
includes taxes & fees
15 Feb - 16 Feb
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
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (260 reviews)
"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
Fireplace

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (178 reviews)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is HK$1,480
HK$1,643 total
includes taxes & fees
25 Feb - 26 Feb
Westbrook Inn B&B
Property entrance

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (224 reviews)
"The property and room was clean, easily accessible, and staff were very friendly. We would stay here again!"
United States
Daren
The price is HK$1,129
HK$1,564 total
includes taxes & fees
15 Mar - 16 Mar
The Sagaponack
Frette Italian sheets, premium bedding, down duvets, pillow-top beds

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (78 reviews)
"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$1,954
HK$2,456 total
includes taxes & fees
15 Mar - 16 Mar
Mill House Inn
Interior detail

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (148 reviews)
"Great spot!"
United States
Keith
Harpoon House
Terrace/patio

The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (91 reviews)
"Beautiful property- wonderful staff- clean, comfortable and relaxed feeling with a lovely breakfast 😄"
United States
Anthony
The price is HK$2,198
HK$2,440 total
includes taxes & fees
19 Feb - 20 Feb
The Homestead
Beach nearby

The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (105 reviews)
"Inn has been newly renovated. Room was spotless. Staff were wonderful. Had an excellent stay. Highly recommend! "
United States
Valerie
The price is HK$2,799
HK$3,275 total
includes taxes & fees
16 Mar - 17 Mar
The Huntting Inn
Terrace/patio

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$4,467
HK$6,443 total
includes taxes & fees
14 Feb - 15 Feb
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

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return! "
Pamela 2-night trip
Posted 7 days ago
The Harbor Front Inn

Find out more about Southold

Southold B&B information

Number of reviews
1,093
Accommodation
38 B&B
Lowest Price
HK$1,564
Highest Price
HK$6,443

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, Horton Lane Beach and McCabe's 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. Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub: 1.3 mi (2.1 km) from the city centre. Enjoy the in-room fireplace and outdoor swimming pool. The Sagaponack: Situated 12 mi (19.3 km) from the heart of Southold. Harpoon House: 9 rooms. 12.4 mi (19.9 km) from the city centre. Enjoy the bars and unique decor. James Pharmacy Bed & Breakfast: 3 rooms. Located 15.5 mi (25 km) from the core of Southold. Enjoy the local cuisine breakfast and designer toiletries.
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 Croteaux Vineyards. You should 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?
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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