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

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Southold bed & breakfast

Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.

1. The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (295 reviews)
"everything about the hotel was excellent, prices fair for the Hamptons!"
United States
Jane
The price is SAR 775
SAR 1,035 total
includes taxes & fees
2 Dec - 3 Dec
The Sagaponack
A living room with a stone fireplace, grey sofas, and a coffee table.

2. The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (285 reviews)
"An excellent choice for our brief stay in Old Saybrook. Clean, comfortable and very well maintained."
United States
Siegfried
The price is SAR 825
SAR 916 total
includes taxes & fees
22 Nov - 23 Nov
The Captain Stannard
A staircase with a white railing, a white chandelier, and framed artwork on the walls.

3. 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 889
SAR 1,016 total
includes taxes & fees
3 Nov - 4 Nov
Harpoon House
A large, white building with a green awning, surrounded by well-maintained lawns and colorful flower beds.

4. The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (133 reviews)
"Good location"
Canada
Josie
The price is SAR 1,344
SAR 1,573 total
includes taxes & fees
16 Nov - 17 Nov
The Huntting Inn
Interior

5. The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.4 out of 10, Exceptional, (252 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
3 Nov - 4 Nov
The Scranton Seahorse Inn
A deck with a wicker sofa and cushions, surrounded by a white fence and trees.

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

Large Room w use of pool/tennis in Spacious home
Sag Harbor
Large Room w use of pool/tennis in Spacious home
A house with a sloped roof, large windows, and a pathway leading to the entrance.

7. 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
3 Nov - 4 Nov
Mill House Inn
A large, multi-story building with a swimming pool, outdoor seating, and a well-maintained garden.

8. 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
3 Nov - 4 Nov
East Hampton Art House Bed & Breakfast
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.

9. The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (112 reviews)
"Charming Inn with great staff and an amazing breakfast."
United States
Sherry
The price is SAR 848
SAR 941 total
includes taxes & fees
9 Nov - 10 Nov
The Homestead
A patio with Adirondack chairs, a fire pit, and a view of a lake.

10. Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (205 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 1,057
SAR 1,173 total
includes taxes & fees
3 Dec - 4 Dec
Westbrook Inn B&B
A dark blue SUV parked on a paved area with trees in the background.

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

Luxury B&B: Pool, Tennis, Free Local Rides
Southampton
Luxury B&B: Pool, Tennis, Free Local Rides
A spacious living room with a large sofa, a coffee table, and a television mounted on the wall.

12. Garden Oasis B&B w/ Pool & Bikes in Southampton

Garden Oasis B&B w/ Pool & Bikes in Southampton
Southampton
Garden Oasis B&B w/ Pool & Bikes in Southampton
A dark-colored SUV parked on a paved surface with a wooded area in the background.

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

Lux Southampton B&B: Pool, Tennis, Gym & Bikes
Southampton
Lux Southampton B&B: Pool, Tennis, Gym & Bikes
A bedroom with a large bed, two bedside lamps, a nightstand, a potted plant, and two framed pictures on the wall.

14. 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
3 Dec - 4 Dec
B&B Near Shinnecock: Pool, Tennis, Beach Access
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

Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"This was my first time at the Hilton Garden Inn. It was clean and the staff was very helpful. Convenient to have breakfast and dinner served at the hotel."
Regina 2-night trip
Posted 5 hours ago
Hilton Garden Inn Riverhead

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.