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

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Check prices for these dates

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov

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
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, (197 reviews)
"Wonderful place great location I definitely recommend!"
United States
Yuliya V
The price is SAR 915
SAR 1,046 total
includes taxes & fees
4 Oct - 5 Oct
Harpoon House
Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.

3. The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (291 reviews)
"everything about the hotel was excellent, prices fair for the Hamptons!"
United States
Jane
The price is SAR 754
SAR 1,011 total
includes taxes & fees
1 Nov - 2 Nov
The Sagaponack
A living room with a stone fireplace, grey sofas, and a coffee table.

4. The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (284 reviews)
"Had a great stay. Everything was fantastic."
United States
Deborah
The price is SAR 747
SAR 829 total
includes taxes & fees
1 Nov - 2 Nov
The Captain Stannard
A dining area with a wooden table, chairs, and a view of greenery through large windows.

5. Carole's Place B & B

Carole's Place B & B
3.0 star property
East Quogue
9.8 out of 10, Exceptional, (87 reviews)
"I really enjoyed our stay here!"
United States
carolyn
The price is SAR 638
SAR 729 total
includes taxes & fees
23 Oct - 24 Oct
Carole's Place B & B
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
The price is SAR 2,146
SAR 3,095 total
includes taxes & fees
2 Oct - 3 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.

7. Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (204 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 1,113
SAR 1,235 total
includes taxes & fees
11 Oct - 12 Oct
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.

8. The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (109 reviews)
"Charming Inn with great staff and an amazing breakfast."
United States
Sherry
The price is SAR 899
SAR 998 total
includes taxes & fees
7 Oct - 8 Oct
The Homestead
Interior

9. The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.0 out of 10, Wonderful, (251 reviews)
"The owner Michael and staff were awesome. Michael makes delicious breakfast. We will definitely stay again. Andersens"
United States
Vicki
The price is SAR 1,148
SAR 1,274 total
includes taxes & fees
1 Nov - 2 Nov
The Scranton Seahorse Inn
A house with a sloped roof, large windows, and a pathway leading to the entrance.

10. 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 1,764 total
includes taxes & fees
14 Oct - 15 Oct
Mill House Inn
A beach with a lifeguard tower, sandy dunes, and the ocean.

11. The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (131 reviews)
"Good location"
Canada
Josie
The price is SAR 1,672
SAR 1,948 total
includes taxes & fees
8 Oct - 9 Oct
The Huntting 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
9.8 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 1,686
SAR 2,148 total
includes taxes & fees
5 Oct - 6 Oct
The Hedges Inn
A large, multi-story building with a swimming pool, outdoor seating, and a well-maintained garden.

13. 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 2,316
SAR 2,646 total
includes taxes & fees
1 Nov - 2 Nov
East Hampton Art House Bed & Breakfast
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 2,910
SAR 3,788 total
includes taxes & fees
1 Nov - 2 Nov
Garden Oasis B&B w/ Pool & Bikes in Southampton
A bedroom with a bed, a window, a desk, and a small table.

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

B&B Near Shinnecock: Pool, Tennis, Beach Access
Southampton
The price is SAR 1,408
SAR 1,827 total
includes taxes & fees
4 Oct - 5 Oct
B&B Near Shinnecock: Pool, Tennis, Beach Access
A dark-colored SUV parked on a paved surface with a wooded area in the background.

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

Lux Southampton B&B: Pool, Tennis, Gym & Bikes
Southampton
The price is SAR 1,577
SAR 2,033 total
includes taxes & fees
13 Oct - 14 Oct
Lux Southampton B&B: Pool, Tennis, Gym & Bikes
A dark blue SUV parked on a paved area with trees in the background.

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

Luxury B&B: Pool, Tennis, Free Local Rides
Southampton
The price is SAR 1,314
SAR 1,716 total
includes taxes & fees
4 Oct - 5 Oct
Luxury B&B: Pool, Tennis, Free Local Rides
A spacious living room with a large sofa, a coffee table, a fireplace, and a television mounted on the wall.

18. Private B&B w/ Pool, Gym, Tennis & Biocharger

Private B&B w/ Pool, Gym, Tennis & Biocharger
Southampton
The price is SAR 1,859
SAR 2,411 total
includes taxes & fees
13 Oct - 14 Oct
Private B&B w/ Pool, Gym, Tennis & Biocharger
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

Zey Hotel

Zey Hotel

10/10 Excellent
"We loved our stay here! The hotel was super cute. We had a room with a beautiful balcony. The location was perfect - right in town walkable to all stores and restaurants. The had parking in the back which was so convenient. We would definitely visit again."
Melissa 2-night trip
Posted less than an hour ago
Zey Hotel

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.