Search B&B in Southold

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare 31 B&B in Southold with updated reviews, rates, and availability.

The Sagaponack
Room

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (133)
"The property was beautiful, and had everything I needed in the room. It was also very clean and easy to control the heat. I loved the location, and I really liked the sheets and room layout. I would suggest providing publications of near by restaurants/bars and activities; Also the staff was very helpful, but its hard to get someone to answer the phone during the day - I had to call more than 6x before someone finally picked up, and its a little concerning that there is no staff after 6pm on the...
The price is AED 585
AED 796 total
includes taxes & fees
6 Feb - 7 Feb
The Sagaponack
Mill House Inn
Front of property

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (65)
"Wonderful stay in a beautiful, historic inn. The staff was always very helpful. My room (I actually got upgraded to an available suite) was gorgeous. Breakfast options were great as well. Thank you again! "
The price is AED 918
AED 1,153 total
includes taxes & fees
9 Feb - 10 Feb
Mill House Inn
The Scranton Seahorse Inn
Front of property

The Scranton Seahorse Inn

3.0 star property
9.0 out of 10, Wonderful, (235)
"Amazing experience!"
The price is AED 992
AED 1,102 total
includes taxes & fees
6 Feb - 7 Feb
The Scranton Seahorse Inn
Carole's Place B & B
Front of property

Carole's Place B & B

3.0 star property
9.6 out of 10, Exceptional, (67)
"We stayed with Carole for two nights, and we absolutely loved her place! The location was perfect for us—central and convenient. From the moment we arrived, we felt right at home. She has created such a warm and cozy space, and her hospitality made all the difference. We truly appreciated her kindness and how welcoming she was. Without a doubt, we’ll be staying with her again the next time we visit Long Island!"
Carole's Place B & B
The Homestead
Exterior

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (76)
"Excellent in every regard. They even have their furnishings listed on line so you can go get for yourself if you want. Staff friendly but not intrusive. Peaceful rooms. Pleasant breakfast. All around very, very nice."
The price is AED 837
AED 929 total
includes taxes & fees
20 Feb - 21 Feb
The Homestead
Westbrook Inn B&B
Dock

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (144)
"Beautiful bed and breakfast with plush robes and slippers, super clean, would stay again!"
The price is AED 789
AED 876 total
includes taxes & fees
5 Feb - 6 Feb
Westbrook Inn B&B
The Huntting Inn
Exterior

The Huntting Inn

3.5 star property
8.6 out of 10, Excellent, (87)
"One of the very few options in East Hampton that offered a one night stay, most have a 2-night minimum. An old, charming inn that was very welcoming and clean. Our king bed room was spacious enough and decorated nicely. The bathroom was very clean and modernized. We did have to walk up a flight of stairs with our luggage which wasn’t difficult for us but may be for some."
The price is AED 1,315
AED 1,538 total
includes taxes & fees
16 Feb - 17 Feb
The Huntting Inn
Harpoon House
Reception

Harpoon House

3.0 star property
8.2 out of 10, Very Good, (109)
"The place and the room were great and extremely well equipped. This was an independent stay, but staff was very efficient and friendly in checking us in."
The price is AED 527
AED 601 total
includes taxes & fees
6 Feb - 7 Feb
Harpoon House
The Captain Stannard B&B Country Inn
Exterior

The Captain Stannard B&B Country Inn

3.0 star property
9.6 out of 10, Exceptional, (214)
"We had a wonderful time and the owner was great. We had a fun time talking about history of both inn’s. Look forward to returning and doing more next time"
The price is AED 862
AED 957 total
includes taxes & fees
13 Feb - 14 Feb
The Captain Stannard B&B Country Inn
434 on Main
Front of property

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
West Neck Guesthouse
Property grounds

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very Good, (32)
"Very convenient location next to Cresent Beach and Leon 1909 restaurant which is fantastic! "
West Neck Guesthouse
The Hedges Inn
Front of property

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (68)
"Super friendly staff, very accommodating! We can’t wait to return. "
The Hedges Inn
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (60)
"Beautiful grounds, pool and hot tub! Beautiful breakfast!"
The price is AED 1,551
AED 1,771 total
includes taxes & fees
3 Feb - 4 Feb
East Hampton Art House Bed & Breakfast
Arbor View House B&B
Room

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (13)
"This house was old but beautiful and decorated nicely inside. "
Arbor View House B&B
Stirling House Bed & Breakfast
Beach/ocean view

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (22)
"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."
The price is AED 1,024
AED 1,169 total
includes taxes & fees
10 Feb - 11 Feb
Stirling House Bed & Breakfast
James Pharmacy Bed & Breakfast
Room

James Pharmacy Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (14)
"We loved staying in the historic pharmacy. We stayed in the Ann Petry room and it is well appointed, clean and charming. The property sits on the town's main street and is very walkable to shopping and dining. We look forward to our next stay. "
The price is AED 1,272
AED 1,852 total
includes taxes & fees
9 Feb - 10 Feb
James Pharmacy Bed & Breakfast
Vine & Sand
Room

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (6)
"My husband and I escaped to Long Island for a beautiful fall weekend and thoroughly enjoyed our stay at Vine + Sand. The hosts were very friendly and helpful with restaurant reservations and offered great tips for local activities. The accommodations were eco-friendly, modern and super comfortable and the breakfast in the morning offered delicious pastries and other homemade foods from local bakeries and markets which were a great touch. The location was private yet close enough to get to town...
Vine & Sand
Historical Bed and breakfast<br>
Exterior

Historical Bed and breakfast<br>

8.6 out of 10, Excellent, (4)
"Very great house , Owner was amazing and was very easy to contact and gave us early check in . Would definitely do it agian"
Historical Bed and breakfast<br>
The Baker House 1650
Exterior

The Baker House 1650

4.5 star property
9.4 out of 10, Exceptional, (33)
"Absolutely best place to stay in East Hampton! Charming B&B with incredible staff. "
The Baker House 1650
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
The bedoom

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
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.
Don't see what you're looking for?
See all available properties in Southold
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Southold

North Fork Dream Getaway, Walk to Private Beach & New In-Ground Pool!
Pool

North Fork Dream Getaway, Walk to Private Beach & New In-Ground Pool!

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved walking down to the beach in the mornings. The house was spacious and clean! Really enjoyed our time! Thank you!"
North Fork Dream Getaway, Walk to Private Beach & New In-Ground Pool!
Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (268)
"Was a winter wonderland. Quiet and clean. Staff were very helpful and kind!"
The price is AED 484
AED 632 total
includes taxes & fees
3 Feb - 4 Feb
Windward Shores Ocean Resort
Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!
Pool

Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!

10.0 out of 10, Exceptional, (34)
"This home is quintessentially charming! I arrived late at night, alone. It has a charming curved drive in and there sat the wood home with a large front porch and Forrest behind it. It seemed like little house on a prairie with the porch and dormer windows. The motion lights went on immediately, which I was grateful for. There is a narrow stairwell up to 3 bedrooms, as is customary in older style homes. High ceilings and windows everywhere enhance this property. When I woke there was a family of...
Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!
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.

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 your ideal vacation to Southold includes spending lots of time outside, Horton Point Park is a good spot to enjoy the scenery.
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. Mill House Inn: 10 rooms. Situated 14.3 mi (23.1 km) from the heart of Southold. Enjoy the free cooked breakfast and designer toiletries. The Baker House 1650: 13 rooms. 14.3 mi (23 km) from the heart of downtown. Enjoy the free full breakfast and designer toiletries.
How many Bed & Breakfasts will I be able to find in Southold?
Expedia has 6 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 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?
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.