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

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Check prices for these dates

Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov
In one month
20 Nov - 22 Nov
In two months
18 Dec - 20 Dec

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, (292 reviews)
"everything about the hotel was excellent, prices fair for the Hamptons!"
United States
Jane
The price is SAR 723
SAR 976 total
includes taxes & fees
19 Nov - 20 Nov
The Sagaponack
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, (205 reviews)
"Wonderful place great location I definitely recommend!"
United States
Yuliya V
The price is SAR 861
SAR 984 total
includes taxes & fees
27 Oct - 28 Oct
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
9.8 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 799
SAR 887 total
includes taxes & fees
29 Oct - 30 Oct
The Captain Stannard
A dining area with a wooden table, chairs, and a view of greenery through large windows.

4. Carole's Place B & B

Carole's Place B & B
3.0 star property
East Quogue
9.8 out of 10, Exceptional, (90 reviews)
"I really enjoyed our stay here!"
United States
carolyn
The price is SAR 563
SAR 643 total
includes taxes & fees
8 Nov - 9 Nov
Carole's Place B & B
A beach chair with a striped cushion and a bag with a floral design.

5. The Hedges Inn

The Hedges Inn
3.5 star property
East Hampton
9.8 out of 10, Exceptional, (83 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 SAR 1,198
SAR 1,590 total
includes taxes & fees
25 Oct - 26 Oct
The Hedges Inn
Three bicycles parked on a lawn with baskets and bags attached, in front of a house with a well-maintained garden and a pathway leading to the entrance.

6. The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (132 reviews)
"Good location"
Canada
Josie
The price is SAR 1,527
SAR 1,782 total
includes taxes & fees
2 Nov - 3 Nov
The Huntting Inn
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
20 Oct - 21 Oct
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
2 Nov - 3 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, (111 reviews)
"Charming Inn with great staff and an amazing breakfast."
United States
Sherry
The price is SAR 875
SAR 971 total
includes taxes & fees
26 Oct - 27 Oct
The Homestead
A deck with a wicker sofa and cushions, surrounded by a white fence and trees.

10. 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 3,093 total
includes taxes & fees
20 Oct - 21 Oct
Large Room w use of pool/tennis in Spacious home
A round outdoor fire pit with flames, surrounded by wicker furniture and a white cushion.

11. 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 1,068
SAR 1,185 total
includes taxes & fees
19 Nov - 20 Nov
Westbrook Inn B&B
Interior

12. The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.0 out of 10, Wonderful, (251 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 SAR 1,058
SAR 1,175 total
includes taxes & fees
2 Nov - 3 Nov
The Scranton Seahorse Inn
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
The price is SAR 1,201
SAR 1,800 total
includes taxes & fees
20 Oct - 21 Oct
Lux Southampton B&B: Pool, Tennis, Gym & Bikes
A spacious living room with a large sofa, a coffee table, and a television mounted on the wall.

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

Garden Oasis B&B w/ Pool & Bikes in Southampton
Southampton
The price is SAR 2,908
SAR 3,785 total
includes taxes & fees
1 Nov - 2 Nov
Garden Oasis B&B w/ Pool & Bikes in Southampton
A bedroom with a bed, a window with blinds, a headboard, a painting of a landscape, and a nightstand with a vase of flowers.

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

B&B Near Shinnecock: Pool, Tennis, Beach Access
Southampton
The price is SAR 1,201
SAR 1,556 total
includes taxes & fees
20 Oct - 21 Oct
B&B Near Shinnecock: Pool, Tennis, Beach Access
A dark blue SUV parked on a paved area with trees in the background.

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

Luxury B&B: Pool, Tennis, Free Local Rides
Southampton
The price is SAR 1,220
SAR 1,595 total
includes taxes & fees
20 Oct - 21 Oct
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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Top Southold Hotel Reviews

The Hampton Maid

The Hampton Maid

10/10 Excellent
"Property and room was incredible. However, didn’t like the restaurant food. It was lacking flavor and the dessert choices weren’t good. Lastly, the pillows weren’t the best."
Delise 2-night trip
Posted 8 hours ago
The Hampton Maid

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.