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

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Check prices for these dates

Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18

Our top choices for Southold bed & breakfast

Premium bedding, iron/ironing board, WiFi (free), bed sheets

1. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.4 out of 10, Very Good, (44 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 P19,274
P22,021 total
includes taxes & fees
Aug 31 - Sep 1
West Neck Guesthouse
Living area

2. The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.6 out of 10, Exceptional, (277 reviews)
"This is a very tastefully decorated B&B in an idyllic location. 6 minute walk to West Beach and near all the famous CT shoreline restaurants and attractions."
United Kingdom
Jessica
The price is P14,381
P15,963 total
includes taxes & fees
Aug 20 - Aug 21
The Captain Stannard
Interior detail

3. Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very Good, (183 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 P17,795
P20,331 total
includes taxes & fees
Sep 1 - Sep 2
Harpoon House
Exterior

4. Arbor View House B&B

Arbor View House B&B
3.5 star property
East Marion
9.4 out of 10, Exceptional, (16 reviews)
"Wonderful stay! Will definitely be back!"
United States
Lekecia
The price is P37,393
P44,046 total
includes taxes & fees
Sep 3 - Sep 4
Arbor View House B&B
Property entrance

5. The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (282 reviews)
"Clean room, great staff, pool is nice and pet friendly."
United States
liliana
The price is P22,787
P29,108 total
includes taxes & fees
Sep 17 - Sep 18
The Sagaponack
Fireplace

6. Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (202 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 P19,846
P22,029 total
includes taxes & fees
Aug 31 - Sep 1
Westbrook Inn B&B
Terrace/patio

7. The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (100 reviews)
"Very enjoyable stay! Love the “house” guitar available to guests."
United States
Mary
The price is P16,137
P17,912 total
includes taxes & fees
Aug 31 - Sep 1
The Homestead
Interior

8. The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.0 out of 10, Wonderful, (246 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 P19,686
P21,851 total
includes taxes & fees
Aug 20 - Aug 21
The Scranton Seahorse Inn
Beach nearby

9. The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (124 reviews)
"Very nice, great place."
United States
James Patrick
The price is P35,034
P40,645 total
includes taxes & fees
Sep 1 - Sep 2
The Huntting Inn
Aerial view

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 P50,596
P57,805 total
includes taxes & fees
Sep 16 - Sep 17
East Hampton Art House Bed & Breakfast
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, (77 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 P38,871
P48,056 total
includes taxes & fees
Sep 13 - Sep 14
The Hedges Inn
Front of property - evening/night

12. 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 P53,795
P77,748 total
includes taxes & fees
Sep 13 - Sep 14
Mill House Inn
Desk, laptop workspace, iron/ironing board, WiFi (free)

13. Head of Pond House

Head of Pond House
3.0 star property
Water Mill
10.0 out of 10, Exceptional, (12 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 P130,128
P148,671 total
includes taxes & fees
Sep 9 - Sep 10
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

The Chequit

The Chequit

10/10 Excellent
"Everything was great ! Wish we had been there when restaurant was open."
Kathleen 1-night trip
Posted 13 hours ago
The Chequit

Find out more about Southold

Southold B&B information

Number of reviews
528
Accommodation
32 B&B
Lowest Price
P15,963
Highest Price
P148,671

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. Mill House Inn: 10 rooms. Located 14.4 mi (23.1 km) from the core of Southold. Enjoy the free cooked breakfast and designer toiletries.
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 Mattebella Vineyards. You might put Croteaux Vineyards and McCabe's Beach 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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