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

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Check prices for these dates

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

Our top choices for Southold bed & breakfast

Deluxe Room, 1 King Bed

1. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (45 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 £263
includes taxes & fees
31 Aug - 1 Sept
West Neck Guesthouse
Living area

2. The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.6 out of 10, Exceptional, (279 reviews)
"Very Friendly staff, very clean everywhere, TVs in main living room and no TVs in rooms which we found awesome actually had time for personal time which we enjoyed"
United States
Joseph
The price is £185
includes taxes & fees
22 Sept - 23 Sept
The Captain Stannard
Exterior

3. 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
Arbor View House B&B
Interior detail

4. Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (184 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 £236
includes taxes & fees
8 Sept - 9 Sept
Harpoon House
Property entrance

5. The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (284 reviews)
"everything about the hotel was excellent, prices fair for the Hamptons!"
United States
Jane
The price is £347
includes taxes & fees
20 Sept - 21 Sept
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 £242
includes taxes & fees
24 Aug - 25 Aug
Westbrook Inn B&B
Interior

7. 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 £287
includes taxes & fees
31 Aug - 1 Sept
The Scranton Seahorse Inn
Room, 1 King Bed, Patio, Ground Floor (2) | Terrace/patio

8. The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (100 reviews)
"Charming Inn with great staff and an amazing breakfast."
United States
Sherry
The price is £203
includes taxes & fees
31 Aug - 1 Sept
The Homestead
Beach

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 £482
includes taxes & fees
1 Sept - 2 Sept
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 £689
includes taxes & fees
7 Sept - 8 Sept
East Hampton Art House Bed & Breakfast
Beach

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 £495
includes taxes & fees
21 Sept - 22 Sept
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 £927
includes taxes & fees
7 Sept - 8 Sept
Mill House Inn
Living area

13. Azur East, southampton

Azur East, southampton
Southampton
The price is £693
includes taxes & fees
1 Sept - 2 Sept
Azur East, southampton
Traditional Cottage, 2 Bedrooms, Lake View (Pet not allowed)

14. 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 £1,763
includes taxes & fees
9 Sept - 10 Sept
Head of Pond House
Property grounds

15. Pool tennis gym Bikes all included & <2m’s fr/ all

Pool tennis gym Bikes all included & <2m’s fr/ all
Southampton
The price is £646
includes taxes & fees
23 Aug - 24 Aug
Pool tennis gym Bikes all included & <2m’s fr/ all
Living area

16. Home 2 mins. from Shinnecock Golf town SH beaches

Home 2 mins. from Shinnecock Golf town SH beaches
Southampton
The price is £680
includes taxes & fees
24 Aug - 25 Aug
Home 2 mins. from Shinnecock Golf town SH beaches
Property grounds

17. Free ride to Shinnecock Golf, SH Town or SH beache

Free ride to Shinnecock Golf, SH Town or SH beache
Southampton
The price is £802
includes taxes & fees
24 Aug - 25 Aug
Free ride to Shinnecock Golf, SH Town or SH beache
Living area

18. Pool Gym Biocharger Tennis Private bath All New BR

Pool Gym Biocharger Tennis Private bath All New BR
Southampton
The price is £768
includes taxes & fees
23 Aug - 24 Aug
Pool Gym Biocharger Tennis Private bath All New BR
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

Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
"Unexpectedly clean and great place. complimentary breakfast was great too. very spacious bathroom a great plus"
Feruza 1-night trip
Posted 2 hours ago
Greenview Inn Riverhead

Find out more about Southold

Southold B&B information

Number of reviews
852
Accommodation
46 B&B
Lowest Price
£185
Highest Price
£1,763

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. 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 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 Mattebella Vineyards. You should 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?
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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