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

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Check prices for these dates

Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4
In one month
Oct 16 - Oct 18
In two months
Nov 13 - Nov 15

Our top choices for Southold bed & breakfast

Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, WiFi (free), bed sheets

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 ￥49,182
￥56,191 total
includes taxes & fees
Oct 1 - Oct 2
West Neck Guesthouse
Property entrance

2. The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (288 reviews)
"everything about the hotel was excellent, prices fair for the Hamptons!"
United States
Jane
The price is ￥35,942
￥47,338 total
includes taxes & fees
Sep 28 - Sep 29
The Sagaponack
Interior detail

3. Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (192 reviews)
"Staff was very courteous and the location was perfect. We would book this venue again for our next trip to the hamptons."
United States
Kim
The price is ￥38,013
￥43,430 total
includes taxes & fees
Oct 7 - Oct 8
Harpoon House
Living area

4. The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (282 reviews)
"Had a great stay. Everything was fantastic."
United States
Deborah
The price is ￥34,129
￥37,883 total
includes taxes & fees
Sep 22 - Sep 23
The Captain Stannard
Fireplace

5. 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 ￥42,988
￥47,716 total
includes taxes & fees
Oct 1 - Oct 2
Westbrook Inn B&B
Room, 1 King Bed, Patio, Ground Floor (2) | Terrace/patio

6. The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (105 reviews)
"Charming Inn with great staff and an amazing breakfast."
United States
Sherry
The price is ￥37,800
￥41,957 total
includes taxes & fees
Sep 23 - Sep 24
The Homestead
Terrace/patio

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 ￥89,657
￥129,319 total
includes taxes & fees
Sep 26 - Sep 27
Large Room w use of pool/tennis in Spacious home
Traditional Cottage, 2 Bedrooms, Lake View (Pet not allowed) | Desk, laptop workspace, iron/ironing board, WiFi (free)

8. Head of Pond House

Head of Pond House
3.0 star property
Water Mill
10.0 out of 10, Exceptional, (14 reviews)
"What a wonderful little gem in the heart of Watermill. This was our favorite Hamptons B&B stay and we can’t wait to comeback!"
United States
Liz
The price is ￥100,045
￥114,302 total
includes taxes & fees
Sep 24 - Sep 25
Head of Pond House
Interior

9. The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.0 out of 10, Wonderful, (249 reviews)
"The owner Michael and staff were awesome. Michael makes delicious breakfast. We will definitely stay again. Andersens"
United States
Vicki
The price is ￥54,972
￥61,019 total
includes taxes & fees
Sep 29 - Sep 30
The Scranton Seahorse Inn
Beach nearby

10. The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (130 reviews)
"Good location"
Canada
Josie
The price is ￥69,860
￥81,383 total
includes taxes & fees
Oct 4 - Oct 5
The Huntting Inn
Beach nearby, sun loungers, beach umbrellas, beach towels

11. The Hedges Inn

The Hedges Inn
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (80 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 ￥56,002
￥73,183 total
includes taxes & fees
Sep 21 - Sep 22
The Hedges Inn
Aerial view

12. 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 ￥107,419
￥122,727 total
includes taxes & fees
Sep 28 - Sep 29
East Hampton Art House Bed & Breakfast
Property grounds

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

Luxury B&B: Pool, Tennis, Free Local Rides
Southampton
The price is ￥46,005
￥60,045 total
includes taxes & fees
Oct 4 - Oct 5
Luxury B&B: Pool, Tennis, Free Local Rides
Front of property - evening/night

14. Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (89 reviews)
"Couldn't have been nicer. Dawn and Tiffany were grcious and accomodating."
Canada
Ronald
The price is ￥136,456
￥197,216 total
includes taxes & fees
Sep 21 - Sep 22
Mill House Inn
Property grounds

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

Lux Southampton B&B: Pool, Tennis, Gym & Bikes
Southampton
The price is ￥58,481
￥75,880 total
includes taxes & fees
Sep 21 - Sep 22
Lux Southampton B&B: Pool, Tennis, Gym & Bikes
Smart TV, offices

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

Private B&B w/ Pool, Gym, Tennis & Biocharger
Southampton
The price is ￥54,583
￥71,271 total
includes taxes & fees
Sep 22 - Sep 23
Private B&B w/ Pool, Gym, Tennis & Biocharger
Smart TV, video games, offices

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

B&B Near Shinnecock: Pool, Tennis, Beach Access
Southampton
The price is ￥54,583
￥70,716 total
includes taxes & fees
Sep 21 - Sep 22
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

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Nice property clean rooms unique having room right on the ocean front was surprised by a pretty nice breakfast many choices food coffee which is always important overall the property is well located to visit surrounding farms and vineyards and short car ride to restaurants and water front"
William B 1-night trip
Posted 3 hours ago
Sound View Greenport

Find out more about Southold

Southold B&B information

Number of reviews
376
Accommodation
46 B&B
Lowest Price
￥37,883
Highest Price
￥197,216

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.

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