Bed and Breakfast in Southold

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Featured B&B in Southold

The Sagaponack
3.0 star property
8.6 out of 10, Excellent, (110)
"Nicely renovated property inbetween Bridgehampton and Southampton. Nice well equipped room. Free snacks, beach access and beach parking pass. "
The price is NZ$345
includes taxes & fees
27 Oct - 28 Oct
The Sagaponack
Harpoon House
3.0 star property
8.2 out of 10, Very good, (107)
"Eclectic, small guest house. The carpeting definitely needed an upgrade but the room was clean very spacious, large bathroom bed was very comfortable. There was a covered deck with large couches which was good for lounging. Wonderful location right in the middle of the town. "
The price is NZ$361
includes taxes & fees
29 Sept - 30 Sept
Harpoon House
The Captain Stannard B&B Country Inn
3.0 star property
9.6 out of 10, Exceptional, (205)
"I had a wonderful and peaceful stay. Loved walking on the beach in the evening and morning. The breakfast was delicious and everything was great!"
The price is NZ$488
includes taxes & fees
27 Sept - 28 Sept
The Captain Stannard B&B Country Inn
The Huntting Inn
3.5 star property
8.6 out of 10, Excellent, (81)
"It was a great location."
The price is NZ$802
includes taxes & fees
13 Oct - 14 Oct
The Huntting Inn
Carole's Place B & B
3.0 star property
9.4 out of 10, Exceptional, (62)
"place was clean. Owner was friendly. Nice experience."
The price is NZ$273
includes taxes & fees
9 Oct - 10 Oct
Carole's Place B & B
The Scranton Seahorse Inn
3.0 star property
9.0 out of 10, Wonderful, (227)
"I would highly recommend the Scranton seahorse in. You will be made to feel like family. And Michael is an extraordinary chef so don’t miss the breakfast."
The price is NZ$431
includes taxes & fees
10 Oct - 11 Oct
The Scranton Seahorse Inn
West Neck Guesthouse
3.5 star property
8.0 out of 10, Very good, (31)
"Very convenient location next to Cresent Beach and Leon 1909 restaurant which is fantastic! "
West Neck Guesthouse
East Hampton Art House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (59)
"Beautiful grounds, pool and hot tub! Beautiful breakfast!"
The price is NZ$1,155
includes taxes & fees
30 Sept - 1 Oct
East Hampton Art House Bed & Breakfast
The Homestead
3.0 star property
10.0 out of 10, Exceptional, (66)
"Fabulous, uniquely decorated B&B with accommodating hosts. Luxurious beds and bedsheets, corner to corner squeaky clean. Will definitely return."
The price is NZ$494
includes taxes & fees
23 Oct - 24 Oct
The Homestead
Mill House Inn
5.0 star property
8.8 out of 10, Excellent, (55)
"Incredible stay at this property with five star service and amazing staff. Every detail was thought through and they truly want to make it the best experience for all their guests. Walking distance to town and nearby shops and restaurants and easy to access other towns and areas from the location. Would highly reccomend!!"
The price is NZ$652
includes taxes & fees
27 Oct - 28 Oct
Mill House Inn
Westbrook Inn B&B
3.0 star property
10.0 out of 10, Exceptional, (139)
"Such a gorgeous Inn! Will definitely return! The rooms are decorated impeccably - large group and each individual bedroom witnessed. I can't wait to dine at breakfast and take a quick trip to the beach before check out. "
The price is NZ$423
includes taxes & fees
8 Oct - 9 Oct
Westbrook Inn B&B
Harbor Knoll Bed & Breakfast
3.0 star property
8.8 out of 10, Excellent, (8)
"Charming bed and breakfast in a great location right on the water…perfect for a romantic getaway!"
Harbor Knoll Bed & Breakfast
434 on Main
4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
Vine & Sand
3.0 star property
10.0 out of 10, Exceptional, (5)
"Johnny and Mark are wonderful hosts! The property was beautifully appointed and maintained, and the breakfast spread was as beautiful as it was delicious complete with fresh eggs from their chickens and fresh tomatoes from their garden. Our room was lovely, and the towels were wonderfully plush. All of the amenities and extra touches made the entire experience extra special."
Vine & Sand
James Pharmacy Bed & Breakfast
4.0 star property
9.6 out of 10, Exceptional, (12)
"This inn provides the traveler with everything they would need and want. Cleanliness, great bedding, great mattress, security, and charming decor."
The price is NZ$728
includes taxes & fees
1 Oct - 2 Oct
James Pharmacy Bed & Breakfast
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."
Stirling House Bed & Breakfast
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
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
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 Farmhouse Bed and Breakfast
4.0 star property
10.0 out of 10, Exceptional, (10)
"Lovely B&B run by a lovely couple"
The Farmhouse Bed and Breakfast
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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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Other property types in Southold

Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (252)
"Very nice place to spend a weekend with friends."
The price is NZ$275
includes taxes & fees
14 Oct - 15 Oct
Windward Shores Ocean Resort
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (202)
"Beautiful condo Convienent Spacious Only issue check in 4 pm Checkout at 10 am "
The price is NZ$638
includes taxes & fees
29 Sept - 30 Sept
Cliffside Resort Condominiums
Gorgeous private Hamptons house with pool and volleyball court
8.6 out of 10, Excellent, (13)
"The house was very spacious, clean and all amenities listed were available to use. Only thing I'd mention is that one of the showers weren't working and we were not able to connect to the wifi but, the host was very responsive during our stay. Late to respond prior to booking but, overall my group had a great experience, the surrounding area is beautiful. The pool and backyard area was nice, I would definitely recommend staying here if you are looking to have a large group gathering with friends...
Gorgeous private Hamptons house with pool and volleyball court
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 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 your ideal holiday 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 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. East Hampton Art House Bed & Breakfast: 2 rooms. Situated 13.9 mi (22.3 km) from the heart of Southold. Enjoy the free full breakfast and fitness centre. Harpoon House: 9 rooms. 12.4 mi (19.9 km) from the city centre. Enjoy the bars and unique decor. The Captain Stannard B&B Country Inn: 11 rooms. Located 15.2 mi (24.4 km) from the core of Southold.
How many bed & breakfasts will I find in Southold?
Expedia has 6 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 Sannino’s Bella Vita Vineyard and The Old Field Vineyards 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.