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

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Check prices for these dates

Next weekend
4 Sep - 6 Sep
In two weeks
11 Sep - 13 Sep
In one month
25 Sep - 27 Sep
In two months
23 Oct - 25 Oct

Our top choices for Southold bed & breakfast

A bedroom with a bed, bedside tables, a lamp, a window, and a door.

1. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (46 reviews)
"It was great! The location was perfect, plenty of amenities close by as well. Easy ferry access depending on time of day. Room was very clean. Will be staying again!"
United States
Allie
The price is 8.182.977 ₫
9.349.214 ₫ total
includes taxes & fees
9 Sept - 10 Sept
West Neck Guesthouse
A staircase with a white railing, a white chandelier, and framed artwork on the walls.

2. Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (186 reviews)
"Staff was very courteous and the location was perfect. We would book this venue again for our next trip to the hamptons."
United States
Kim
The price is 7.350.323 ₫
8.397.743 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Harpoon House
A living room with a stone fireplace, grey sofas, and a coffee table.

3. The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.6 out of 10, Exceptional, (280 reviews)
"Very Friendly staff, very clean everywhere, TVs in main living room and no TVs in rooms which we found awesome actually had time for personal time which we enjoyed"
United States
Joseph
The price is 6.105.754 ₫
6.777.387 ₫ total
includes taxes & fees
8 Sept - 9 Sept
The Captain Stannard
Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.

4. The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (285 reviews)
"everything about the hotel was excellent, prices fair for the Hamptons!"
United States
Jane
The price is 8.901.304 ₫
11.474.839 ₫ total
includes taxes & fees
13 Sept - 14 Sept
The Sagaponack
A round outdoor fire pit with flames, surrounded by wicker furniture and a white cushion.

5. Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (202 reviews)
"This place is always the best love the rooms. The staff is excellent place is so clean always feel so comfortable here."
United States
Diane
The price is 8.425.726 ₫
9.352.555 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Westbrook Inn B&B
A red door with a 'Gone to the Beach' sign, a wicker chair, a table with a plate of food and drinks, and a potted plant.

6. The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (101 reviews)
"Charming Inn with great staff and an amazing breakfast."
United States
Sherry
The price is 6.977.065 ₫
7.744.464 ₫ total
includes taxes & fees
14 Sept - 15 Sept
The Homestead
A large, multi-story building with a swimming pool, outdoor seating, and a well-maintained garden.

7. East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
4.0 star property
Clearwater Beach
9.6 out of 10, Exceptional, (65 reviews)
"The hosts were really nice and the breakfast is excellent!"
United States
IVAN
The price is 19.845.873 ₫
22.673.764 ₫ total
includes taxes & fees
27 Sept - 28 Sept
East Hampton Art House Bed & Breakfast

8. The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.0 out of 10, Wonderful, (247 reviews)
"Excellent B&B. Great breakfast. Lovely area. Walk around to local stores and restaurants. And beach is nearby."
United States
Krishna
The price is 9.788.250 ₫
10.864.957 ₫ total
includes taxes & fees
9 Sept - 10 Sept
The Scranton Seahorse Inn
A beach with a lifeguard tower, sandy dunes, and the ocean.

9. The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (124 reviews)
"Very nice, great place."
United States
James Patrick
The price is 14.799.573 ₫
17.169.896 ₫ total
includes taxes & fees
27 Sept - 28 Sept
The Huntting Inn
A two-story house with a steeply pitched roof, green shutters, and a brick entrance.

10. Head of Pond House

Head of Pond House
3.0 star property
Water Mill
10.0 out of 10, Exceptional, (13 reviews)
"What a wonderful little gem in the heart of Watermill. This was our favorite Hamptons B&B stay and we can’t wait to comeback!"
United States
Liz
The price is 55.002.402 ₫
62.840.244 ₫ total
includes taxes & fees
9 Sept - 10 Sept
Head of Pond House
A house with a sloped roof, large windows, and a pathway leading to the entrance.

11. Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (89 reviews)
"Couldn't have been nicer. Dawn and Tiffany were grcious and accomodating."
Canada
Ronald
The price is 22.839.250 ₫
33.008.850 ₫ total
includes taxes & fees
10 Sept - 11 Sept
Mill House Inn
A beach chair with a striped cushion and a bag with a floral design.

12. The Hedges Inn

The Hedges Inn
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (77 reviews)
"The staff was warm, welcoming, knowledgeable & helpful! The food was superb! The room was impeccable from cleanliness to the amenities provided! We absolutely loved our stay and cannot wait to return. "
United States
Lauren
The price is 14.071.588 ₫
17.616.762 ₫ total
includes taxes & fees
21 Sept - 22 Sept
The Hedges Inn
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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Just an outstanding hotel in a breathtakingly beautiful setting!! I couldn’t be more impressed & look forward to returning! 10 stars!!"
Joan 2-night trip
Posted 14 hours ago
Water's Edge Resort & Spa

Find out more about Southold

Southold B&B information

Number of reviews
945
Accommodation
30 B&B
Lowest Price
6.777.387 ₫
Highest Price
62.840.244 ₫

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.
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 Sannino's Bella Vita Vineyard and Custer Institute and Observatory 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.

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