Find a Bed and Breakfast in Southold from CA $327

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Check prices for these dates

Next weekend
May 15 - May 17
In two weeks
May 22 - May 24
In one month
Jun 5 - Jun 7
In two months
Jul 3 - Jul 5

Our top choices for Southold bed & breakfast

Interior

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (16 reviews)
"Wonderful stay"
United States
Judy
The price is CA $574
CA $656 total
includes taxes & fees
May 18 - May 19
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 CA $438
CA $569 total
includes taxes & fees
May 11 - May 12
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 CA $477
CA $620 total
includes taxes & fees
May 11 - May 12
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 CA $438
CA $569 total
includes taxes & fees
May 11 - May 12
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 CA $477
CA $620 total
includes taxes & fees
May 11 - May 12
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
9.6 out of 10, Exceptional, (263 reviews)
"Very clean, easy check-in, lovely owners."
United States
GAIL
The price is CA $294
CA $327 total
includes taxes & fees
May 26 - May 27
The Captain Stannard
Interior

The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.0 out of 10, Wonderful, (242 reviews)
"We had a wonderful stay. Perfect location, great staff, and check-in process, and our room was delightful."
United States
Brian
The price is CA $414
CA $459 total
includes taxes & fees
May 25 - May 26
The Scranton Seahorse Inn
Interior detail

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (150 reviews)
"Room was clean. Bathroom was refinished. "
United States
robert
The price is CA $356
CA $406 total
includes taxes & fees
May 11 - May 12
Harpoon House
Property entrance

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (256 reviews)
"Room was very clean and staff very friendly!"
United States
Dawn
The price is CA $409
CA $515 total
includes taxes & fees
Jun 8 - Jun 9
The Sagaponack
Fireplace

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (191 reviews)
"Breakfast was amazing! Staff was so kind, and place was very clean. "
United States
Ashley
The price is CA $406
CA $451 total
includes taxes & fees
May 25 - May 26
Westbrook Inn B&B
Front of property - evening/night

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (84 reviews)
"The breakfast is amazing, beds super comfortable and grounds stunning. Location was perfect and staff wonderful. Also the tub in our room was incredible. Only suggestion would be for coffee in the room in the morning. Otherwise it was a literal perfect stay "
United States
Jessica
The price is CA $615
CA $774 total
includes taxes & fees
May 21 - May 22
Mill House Inn
Deluxe Room, 1 King Bed

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.0 out of 10, Very good, (37 reviews)
"Great property! Close to beach and super clean. "
United States
Leslie
The price is CA $299
CA $342 total
includes taxes & fees
May 31 - Jun 1
West Neck Guesthouse
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, (92 reviews)
"Beautiful property- wonderful staff- clean, comfortable and relaxed feeling with a lovely breakfast 😄"
United States
Anthony
The price is CA $491
CA $545 total
includes taxes & fees
May 12 - May 13
The Homestead
Outdoor dining

Stirling House Bed & Breakfast

Stirling House Bed & Breakfast
3.0 star property
Greenport
9.8 out of 10, Exceptional, (24 reviews)
"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."
United States
steve
The price is CA $688
CA $786 total
includes taxes & fees
May 15 - May 16
Stirling House Bed & Breakfast
Beach nearby

The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (105 reviews)
"Rooms are wonderful, quiet and the location cannot be beat. "
United States
Sophie
The price is CA $625
CA $727 total
includes taxes & fees
May 13 - May 14
The Huntting Inn
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

Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

6/10 Okay
"Other than the housekeeping staff and the bartender everyone else was not welcoming and seemed annoyed when asked a question. "
Daisy 2-night trip
Posted 2 hours ago
Hilton Garden Inn Riverhead

Find out more about Southold

Southold B&B information

Number of reviews
1,286
Accommodation
34 B&B
Lowest Price
CA $327
Highest Price
CA $786

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 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 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. The Huntting Inn: 19 rooms. 14.4 mi (23.1 km) from the heart of downtown. Enjoy the fireplace in the lobby and bar/lounge. Mill House Inn: 10 rooms. Located 14.4 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 5 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 Mattebella Vineyards. You might put Croteaux Vineyards and Horton Lane Beach 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.

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