Bed and Breakfast in Southold

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Check prices for these dates

Next weekend
27 Mar - 29 Mar
In two weeks
3 Apr - 5 Apr
In one month
17 Apr - 19 Apr
In two months
15 May - 17 May

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 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 NZ$691
includes taxes & fees
22 Mar - 23 Mar
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 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 NZ$759
includes taxes & fees
22 Mar - 23 Mar
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 NZ$691
includes taxes & fees
22 Mar - 23 Mar
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 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 NZ$759
includes taxes & fees
22 Mar - 23 Mar
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Interior detail

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (149 reviews)
"Great spot!"
United States
Keith
Harpoon House
Fireplace

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (180 reviews)
"Delicious breakfast, wonderful service and beautiful accommodations."
United States
Beth
The price is NZ$363
includes taxes & fees
23 Mar - 24 Mar
Westbrook Inn B&B
IPod dock, MP3 dock

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (261 reviews)
"Classic inn- great breakfast"
United States
John
The Captain Stannard
Property entrance

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (229 reviews)
"Very charming, I stayed in one of the cottages, comfortable and well equipped."
United States
Gina
The price is NZ$377
includes taxes & fees
23 Mar - 24 Mar
The Sagaponack
Graybarn Cottage

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (81 reviews)
"It is a very nice place, the staff is very friendly and the breakfast is very good. Also they have delicious teas, coffee, hot cider and snacks. We definitely recommend this hotel "
United States
Eliane
The price is NZ$543
includes taxes & fees
22 Mar - 23 Mar
Mill House Inn
Miss Anna James Room

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23 reviews)
"Cute B&B, very nice room, check-in worked well"
United States
Isolde
The price is NZ$579
includes taxes & fees
1 Apr - 2 Apr
James Pharmacy Bed & Breakfast
Room, 1 King Bed, Patio, Ground Floor (2) | 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 NZ$539
includes taxes & fees
26 Mar - 27 Mar
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 NZ$766
includes taxes & fees
23 Mar - 24 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 NZ$1,369
includes taxes & fees
20 Mar - 21 Mar
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 Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"By far one of the best hotels I’ve ever stayed at. The bed was heaven, the room was huge and decorated so well! "
Jessica 1-night trip
Posted 1 day ago
The Bentley Hotel Southampton

Find out more about Southold

Southold B&B information

Number of reviews
1,112
Accommodation
38 B&B
Lowest Price
NZ$363
Highest Price
NZ$1,369

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. The Sagaponack: 12 mi (19.3 km) from the city centre. Harpoon House: 9 rooms. Situated 12.4 mi (19.9 km) from the heart of Southold. Enjoy the bars and unique decor. Mill House Inn: 10 rooms. 14.4 mi (23.1 km) from the city centre. Enjoy the free cooked breakfast and designer toiletries. Carole's Place B & B: 2 rooms. Located 17.2 mi (27.7 km) from the core of Southold. Enjoy the free full breakfast and outdoor pool.
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 Croteaux Vineyards and Osprey's Dominion. 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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