A calm lake with a forest in the background during sunset.

Search B&B in Southold

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul
In one month
31 Jul - 2 Aug
In two months
28 Aug - 30 Aug

Our top choices for Southold bed & breakfast

IPod dock, MP3 dock

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (267 reviews)
"Very clean, easy check-in, lovely owners."
United States
GAIL
The price is HK$1,834
HK$2,036 total
includes taxes & fees
8 Jul - 9 Jul
The Captain Stannard
Interior detail

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (167 reviews)
"Hotel staff were more than a accommodating, the rooms were unique ,warm and welcoming, Voss waters and expresso in the room . Bedding was marvelous and the bright walk-in glass showers were clean and spacious. The hotel is Steps away from delicious food options while youe neighborhood Starbucks and CVS around the corner. Definitely would stay again ! Amazing place. Full of charm you would expect from a 400 year old property."
United States
VINCENT M
The price is HK$3,444
HK$3,934 total
includes taxes & fees
22 Jul - 23 Jul
Harpoon House
Fireplace

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (195 reviews)
"Breakfast was amazing! Staff was so kind, and place was very clean. "
United States
Ashley
The price is HK$2,531
HK$2,809 total
includes taxes & fees
22 Jul - 23 Jul
Westbrook Inn B&B
Interior

The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.0 out of 10, Wonderful, (243 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 HK$2,776
HK$3,081 total
includes taxes & fees
2 Jul - 3 Jul
The Scranton Seahorse Inn
Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (41 reviews)
"Great property! Close to beach and super clean. "
United States
Leslie
The price is HK$2,458
HK$2,808 total
includes taxes & fees
16 Jul - 17 Jul
West Neck Guesthouse
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 HK$2,902
HK$3,221 total
includes taxes & fees
12 Jul - 13 Jul
The Homestead
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, (86 reviews)
"Proximity to East Hampton stores - so close you can walk to most things, biggest asset of this property. Room was nice, bedding excellent."
United States
Rhett
The price is HK$7,089
HK$10,387 total
includes taxes & fees
16 Jul - 17 Jul
Mill House Inn
Property entrance

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (270 reviews)
"Staff - room - coffee was excellent! Would highly recommend!"
United States
Michael
The price is HK$3,913
HK$4,862 total
includes taxes & fees
20 Jul - 21 Jul
The Sagaponack
Beach nearby

The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (113 reviews)
"Amazing location, right on Main Street in East Hampton, great staff, rooms and breakfast"
United States
EDUARD
The price is HK$5,002
HK$5,793 total
includes taxes & fees
7 Jul - 8 Jul
The Huntting Inn
Beach nearby, sun-loungers, beach umbrellas, beach towels

The Hedges Inn

The Hedges Inn
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (73 reviews)
"Excellent place"
United States
Miguel
The price is HK$7,050
HK$8,517 total
includes taxes & fees
7 Jul - 8 Jul
The Hedges Inn
Smart TV, video games, offices

Home 2 mins. from Shinnecock Golf town SH beaches

Home 2 mins. from Shinnecock Golf town SH beaches
Southampton
The price is HK$3,294
HK$5,995 total
includes taxes & fees
13 Jul - 14 Jul
Home 2 mins. from Shinnecock Golf town SH beaches
Property grounds

Free ride to Shinnecock Golf, SH Town or SH beache

Free ride to Shinnecock Golf, SH Town or SH beache
Southampton
The price is HK$4,893
HK$8,428 total
includes taxes & fees
26 Jul - 27 Jul
Free ride to Shinnecock Golf, SH Town or SH beache
Property grounds

Pool tennis gym Bikes all included & <2m’s fr/ all

Pool tennis gym Bikes all included & <2m’s fr/ all
Southampton
The price is HK$3,098
HK$5,773 total
includes taxes & fees
26 Jul - 27 Jul
Pool tennis gym Bikes all included & <2m’s fr/ all
Property grounds

2 minute free ride to Shinnecock Golf US Open

2 minute free ride to Shinnecock Golf US Open
Southampton
The price is HK$6,885
HK$19,740 total
includes taxes & fees
6 Jul - 7 Jul
2 minute free ride to Shinnecock Golf US Open
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southold Hotel Reviews

The Bentley Hotel Southampton

The Bentley Hotel Southampton

8/10 Good
"We love to stay at this location due to the location and size of the room. We will be going back for sure!"
Jeremy 1-night trip
Posted less than an hour ago
The Bentley Hotel Southampton

Find out more about Southold

Southold B&B information

Number of reviews
1,126
Accommodation
47 B&B
Lowest Price
HK$2,036
Highest Price
HK$19,740

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. The Huntting Inn: 19 rooms. 14.4 mi (23.1 km) from the city centre. Enjoy the fireplace in reception 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 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.

Explore a world of travel with Expedia