Bed and Breakfast in Southold

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Check prices for these dates

Next weekend
12 Sept - 14 Sept
In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

Featured B&B in Southold

Our top choices for Southold bed & breakfast

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (174)
"Great stay!"
The price is NZ$533
includes taxes & fees
6 Oct - 7 Oct
The Sagaponack
The Huntting Inn
Garden

The Huntting Inn

3.5 star property
8.8 out of 10, Excellent, (101)
"Great property."
The price is NZ$948
includes taxes & fees
5 Oct - 6 Oct
The Huntting Inn
Harpoon House
Porch

Harpoon House

3.0 star property
8.4 out of 10, Very good, (135)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
Harpoon House
The Captain Stannard
IPod dock, MP3 dock

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (244)
"Everything was fantastic, will stay again!"
The Captain Stannard
The Hedges Inn
Room One: Large Queen Guestroom

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (71)
"Great staff "
The price is NZ$785
includes taxes & fees
7 Sept - 8 Sept
The Hedges Inn
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (162)
"Beautiful place and wonderful staff"
The price is NZ$401
includes taxes & fees
28 Sept - 29 Sept
Westbrook Inn B&B
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
The price is NZ$949
includes taxes & fees
1 Oct - 2 Oct
Mill House Inn
The Homestead
Room, 1 King Bed, Patio, Ground Floor (7)

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (85)
"This is our 2nd year staying at the Homestead B & B. We absolutely love it here! Great food, amenities galore, and just an awesome getaway!"
The Homestead
James Pharmacy Bed & Breakfast
Miss Anna James Room

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (18)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
The price is NZ$614
includes taxes & fees
2 Oct - 3 Oct
James Pharmacy Bed & Breakfast
Carole's Place B & B
Property grounds

Carole's Place B & B

3.0 star property
9.8 out of 10, Exceptional, (53)
"It’s a very charming place and well located."
Carole's Place B & B
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (64)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
The price is NZ$1,106
includes taxes & fees
1 Oct - 2 Oct
East Hampton Art House Bed & Breakfast
West Neck Guesthouse
Deluxe Room, 1 King Bed

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very good, (37)
"Great property! Close to beach and super clean. "
The price is NZ$608
includes taxes & fees
9 Sept - 10 Sept
West Neck Guesthouse
Vine & Sand
Interior entrance

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (10)
"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. "
Vine & Sand
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (36)
"Great hosts"
434 on Main
Harbor Knoll Bed & Breakfast
Living area

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (10)
"Beautiful bed and breakfast with gorgeous views. Close to shops and restaurants but far enough to be private and quiet. Will definitely be coming back"
Harbor Knoll Bed & Breakfast
Arbor View House B&B
Exterior

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (15)
"Two mid age couples just had a good and relaxing time with great hospitality. "
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, (24)
"Our stay was only 2 nights but felt like 5. Well rested 3 days. Would return in a Heart Beat. Clay was awesome and the breakfasts were over the top !"
Stirling House Bed & Breakfast
The 1708 House
Exterior

The 1708 House

3.0 star property
10.0 out of 10, Exceptional, (2)
"We absolutely loved our stay here. The house is stunning, the service is fabulous. The best bed ever to sleep in! Great location and a fabulous breakfast. Thank you. "
The 1708 House
Head of Pond House
Exterior

Head of Pond House

3.0 star property
Head of Pond House
Historical Bed and breakfast<br>
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Historical Bed and breakfast<br>

8.8 out of 10, Excellent, (5)
"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>
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

Find out more about Southold

Find out more about Southold

Southold B&B information

Number of reviews
Accommodation
38 B&B
Lowest Price
NZ$401
Highest Price
NZ$1,106

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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, McCabe's Beach and Horton Lane 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. The Captain Stannard: 11 rooms. Situated 15.2 mi (24.4 km) from the heart of Southold. Enjoy the private garden and unique decor. Harpoon House: 9 rooms. 12.4 mi (19.9 km) from the city centre. Enjoy the bars and unique decor. East Hampton Art House Bed & Breakfast: 2 rooms. Located 13.9 mi (22.3 km) from the core of Southold. Enjoy the free full breakfast and fitness centre.
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 Osprey's Dominion 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.