Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA

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Check prices for these dates

Next weekend
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul
In one month
17 Jul - 19 Jul
In two months
14 Aug - 16 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, (266 reviews)
"Very clean, easy check-in, lovely owners."
United States
GAIL
The price is AED 780
AED 865 total
includes taxes & fees
28 Jun - 29 Jun
The Captain Stannard
Deluxe Room, 1 King Bed | 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, (39 reviews)
"Great property! Close to beach and super clean. "
United States
Leslie
The price is AED 804
AED 919 total
includes taxes & fees
22 Jun - 23 Jun
West Neck Guesthouse
Fireplace

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (194 reviews)
"Breakfast was amazing! Staff was so kind, and place was very clean. "
United States
Ashley
The price is AED 1,115
AED 1,238 total
includes taxes & fees
25 Jun - 26 Jun
Westbrook Inn B&B
Interior detail

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very Good, (161 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 AED 1,308
AED 1,494 total
includes taxes & fees
23 Jun - 24 Jun
Harpoon House
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 AED 1,300
AED 1,443 total
includes taxes & fees
22 Jun - 23 Jun
The Scranton Seahorse Inn
Property entrance

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (263 reviews)
"Staff - room - coffee was excellent! Would highly recommend!"
United States
Michael
The price is AED 1,312
AED 1,866 total
includes taxes & fees
23 Jun - 24 Jun
The Sagaponack
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, (85 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 AED 2,568
AED 3,920 total
includes taxes & fees
22 Jun - 23 Jun
Mill House Inn
Beach nearby

The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (110 reviews)
"Amazing location, right on Main Street in East Hampton, great staff, rooms and breakfast"
United States
EDUARD
The price is AED 2,213
AED 2,565 total
includes taxes & fees
6 Jul - 7 Jul
The Huntting Inn
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 AED 1,282
AED 1,423 total
includes taxes & fees
22 Jun - 23 Jun
The Homestead
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 AED 2,641
AED 3,234 total
includes taxes & fees
22 Jun - 23 Jun
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 AED 1,451
AED 2,065 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 AED 1,818
AED 2,543 total
includes taxes & fees
12 Jul - 13 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 AED 1,888
AED 2,631 total
includes taxes & fees
12 Jul - 13 Jul
Pool tennis gym Bikes all included & <2m’s fr/ all
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

Sound View Greenport

Sound View Greenport

10/10 Excellent
"The Soundview is one of my favorite hotels in greenport ( favorite) we had an amazing room I never wanted to leave!!"
robyn 2-night trip
Posted 12 hours ago
Sound View Greenport

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 The Old Field 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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