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
The price is HK$2,459
HK$2,810 total
includes taxes & fees
1 Oct - 2 Oct
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, (195 reviews)
"Wonderful place great location I definitely recommend!"
United States
Yuliya V
The price is HK$1,912
HK$2,185 total
includes taxes & fees
1 Oct - 2 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, (289 reviews)
"everything about the hotel was excellent, prices fair for the Hamptons!"
United States
Jane
The price is HK$1,889
HK$2,472 total
includes taxes & fees
1 Oct - 2 Oct
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 HK$1,835
HK$2,037 total
includes taxes & fees
30 Sept - 1 Oct
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 HK$1,333
HK$1,524 total
includes taxes & fees
23 Oct - 24 Oct
Carole's Place B & B
A round outdoor fire pit with flames, surrounded by wicker furniture and a white cushion.

6. Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (203 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 HK$2,325
HK$2,581 total
includes taxes & fees
1 Oct - 2 Oct
Westbrook Inn B&B
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 HK$4,483
HK$6,063 total
includes taxes & fees
30 Sept - 1 Oct
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, (109 reviews)
"Charming Inn with great staff and an amazing breakfast."
United States
Sherry
The price is HK$1,892
HK$2,100 total
includes taxes & fees
7 Oct - 8 Oct
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, (89 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 HK$2,549
HK$3,684 total
includes taxes & fees
13 Oct - 14 Oct
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 HK$5,371
HK$6,136 total
includes taxes & fees
30 Sept - 1 Oct
East Hampton Art House Bed & Breakfast
A beach chair with a striped cushion and a bag with a floral design.

11. The Hedges Inn

The Hedges Inn
3.5 star property
East Hampton
9.8 out of 10, Exceptional, (82 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 HK$3,131
HK$4,040 total
includes taxes & fees
26 Oct - 27 Oct
The Hedges Inn
A beach with a lifeguard tower, sandy dunes, and the ocean.

12. 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 HK$3,493
HK$4,069 total
includes taxes & fees
4 Oct - 5 Oct
The Huntting Inn
Interior

13. 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 HK$2,777
HK$3,082 total
includes taxes & fees
6 Oct - 7 Oct
The Scranton Seahorse Inn
A spacious living room with a large sofa, a coffee table, a fireplace, and a television mounted on the wall.

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

B&B Near Shinnecock: Pool, Tennis, Beach Access
Southampton
The price is HK$2,942
HK$3,602 total
includes taxes & fees
30 Sept - 1 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.

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

Lux Southampton B&B: Pool, Tennis, Gym & Bikes
Southampton
The price is HK$3,294
HK$4,041 total
includes taxes & fees
30 Sept - 1 Oct
Lux Southampton B&B: Pool, Tennis, Gym & Bikes
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 HK$3,530
HK$4,356 total
includes taxes & fees
30 Sept - 1 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.

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

Private B&B w/ Pool, Gym, Tennis & Biocharger
Southampton
The price is HK$3,883
HK$4,759 total
includes taxes & fees
30 Sept - 1 Oct
Private B&B w/ Pool, Gym, Tennis & Biocharger
A two-story house with a steeply pitched roof, green shutters, and a brick entrance.

18. Head of Pond House

Head of Pond House
3.0 star property
Water Mill
10.0 out of 10, Exceptional, (16 reviews)
"Excellent European B&B experience not often found in the States. A quaint well-managed property with hidden charm. The bedrooms were spacious , comfortable and nicely designed with taste and simplicity."
United States
neil
Head of Pond House
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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Although a budget property, staff was helpful and the property is well-maintained. We were pleasantly surprised by the quality of our stay."
Michael 1-night trip
Posted less than an hour ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Southold

Southold B&B information

Number of reviews
887
Accommodation
46 B&B
Lowest Price
HK$1,524
Highest Price
HK$6,136

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.
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 city centre. Harpoon House: 9 rooms. Situated 12.4 mi (19.9 km) from the heart of Southold. Enjoy the bars and unique decor. The Hedges Inn: 12 rooms. 14.4 mi (23.1 km) from the city centre. 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 snack bar/deli and unique decor.
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 The Old Field Vineyards 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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