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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Southold bed & breakfast

A staircase with a white railing, a white chandelier, and framed artwork on the walls.

1. Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (210 reviews)
"Wonderful place great location I definitely recommend!"
United States
Yuliya V
The price is SAR 551
SAR 630 total
includes taxes & fees
14 Nov - 15 Nov
Harpoon House
Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.

2. The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (298 reviews)
"We loved the 1 bedroom bungalow! One could sleep while the other read or watched TV. The bed was very comfortable. The kitchenette was very convenient. While there was a little road noise, the thoughtfully provided sound machine canceled that out. The best part for us was the location; right in the middle of the Hamptons, Montauck and Sag Harbor. Would definitely stay here again!"
United States
PAUL
The price is SAR 772
SAR 1,032 total
includes taxes & fees
15 Nov - 16 Nov
The Sagaponack
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
9.8 out of 10, Exceptional, (286 reviews)
"An excellent choice for our brief stay in Old Saybrook. Clean, comfortable and very well maintained."
United States
Siegfried
The price is SAR 683
SAR 758 total
includes taxes & fees
15 Nov - 16 Nov
The Captain Stannard
A round outdoor fire pit with flames, surrounded by wicker furniture and a white cushion.

4. Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (206 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 SAR 779
SAR 864 total
includes taxes & fees
18 Nov - 19 Nov
Westbrook Inn B&B
A beach with a lifeguard tower, sandy dunes, and the ocean.

5. The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (134 reviews)
"Good location"
Canada
Josie
The price is SAR 1,344
SAR 1,573 total
includes taxes & fees
29 Nov - 30 Nov
The Huntting Inn
Interior

6. The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.4 out of 10, Exceptional, (253 reviews)
"A lovely stay at a classic New England B & B. Perfect location for a visit to Madison."
United States
Tracy
The price is SAR 881
SAR 978 total
includes taxes & fees
16 Nov - 17 Nov
The Scranton Seahorse Inn
A deck with a wicker sofa and cushions, surrounded by a white fence and trees.

7. Large Room w use of pool/tennis in Spacious home

Large Room w use of pool/tennis in Spacious home
Sag Harbor
The price is SAR 2,145
SAR 2,939 total
includes taxes & fees
14 Nov - 15 Nov
Large Room w use of pool/tennis in Spacious home
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.

8. The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (114 reviews)
"Beautiful and unique inn with great staff."
United States
Anita C
The price is SAR 801
SAR 889 total
includes taxes & fees
23 Nov - 24 Nov
The Homestead
A house with a sloped roof, large windows, and a pathway leading to the entrance.

9. Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (90 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 SAR 1,220
SAR 1,763 total
includes taxes & fees
17 Nov - 18 Nov
Mill House Inn
A large, multi-story building with a swimming pool, outdoor seating, and a well-maintained garden.

10. 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 SAR 1,697
SAR 1,939 total
includes taxes & fees
23 Nov - 24 Nov
East Hampton Art House Bed & Breakfast
A dark-colored SUV parked on a paved surface with a wooded area in the background.

11. Lux Southampton B&B: Pool, Tennis, Gym & Bikes

Lux Southampton B&B: Pool, Tennis, Gym & Bikes
Southampton
The price is SAR 1,201
SAR 1,710 total
includes taxes & fees
13 Dec - 14 Dec
Lux Southampton B&B: Pool, Tennis, Gym & Bikes
A dark blue SUV parked on a paved surface with a wooded area in the background.

12. Less Than 2 Miles from Shinnecock Hills Golf Club

Less Than 2 Miles from Shinnecock Hills Golf Club
Southampton
Less Than 2 Miles from Shinnecock Hills Golf Club
A bedroom with a large bed, two bedside lamps, a nightstand, a potted plant, and two framed pictures on the wall.

13. B&B Near Shinnecock: Pool, Tennis, Beach Access

B&B Near Shinnecock: Pool, Tennis, Beach Access
Southampton
The price is SAR 1,201
SAR 1,479 total
includes taxes & fees
14 Dec - 15 Dec
B&B Near Shinnecock: Pool, Tennis, Beach Access
A dark blue SUV parked on a paved area with trees in the background.

14. Luxury B&B: Pool, Tennis, Free Local Rides

Luxury B&B: Pool, Tennis, Free Local Rides
Southampton
The price is SAR 1,220
SAR 1,514 total
includes taxes & fees
15 Nov - 16 Nov
Luxury B&B: Pool, Tennis, Free Local Rides
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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Learn more about Southold

Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip.

See all hotels in Southold
A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.

Top reviews in Southold

A living room with a stone fireplace, grey sofas, and a coffee table.
The Captain Stannard

The Captain Stannard

The Captain Stannard
Westbrook Center

10/10 Excellent

The Captain Stannard house is a true gem in Westbrook. There are many restaurants, shops, parks, and beaches close by. The property has a private yard and a large rear porch for relaxation. My room was impeccably clean and spacious for being the smallest one in the house. Dianne was incredibly sweet and went out of her way to help all the guests.
United States
Julie
Reviewed May 27, 2024
The Captain Stannard

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, 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 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 Hedges Inn: 12 rooms. 14.4 mi (23.1 km) from the heart of downtown. Enjoy the free cooked breakfast and designer toiletries. The Homestead: 10 rooms. Located 17.8 mi (28.6 km) from the core of Southold. Enjoy the deli and unique décor.

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 Croteaux Vineyards. You might 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?

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.