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

Search Southold Bed & Breakfast

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
18 Sept - 20 Sept
In two weeks
25 Sept - 27 Sept
In one month
9 Oct - 11 Oct
In two months
6 Nov - 8 Nov

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, (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 AU$500
includes taxes & fees
15 Sept - 16 Sept
West Neck Guesthouse
Interior detail

2. Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (191 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 AU$382
includes taxes & fees
14 Sept - 15 Sept
Harpoon House
Property entrance

3. The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (286 reviews)
"everything about the hotel was excellent, prices fair for the Hamptons!"
United States
Jane
The price is AU$474
includes taxes & fees
12 Oct - 13 Oct
The Sagaponack
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 AU$362
includes taxes & fees
14 Sept - 15 Sept
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 AU$422
includes taxes & fees
29 Sept - 30 Sept
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 AU$389
includes taxes & fees
14 Sept - 15 Sept
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 AU$1,234
includes taxes & fees
26 Sept - 27 Sept
Large Room w use of pool/tennis in Spacious home
Interior

8. 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 AU$546
includes taxes & fees
23 Sept - 24 Sept
The Scranton Seahorse Inn
Aerial view

9. 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 AU$1,091
includes taxes & fees
28 Sept - 29 Sept
East Hampton Art House Bed & Breakfast
Beach nearby

10. The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (128 reviews)
"Good location"
Canada
Josie
The price is AU$724
includes taxes & fees
4 Oct - 5 Oct
The Huntting Inn
Traditional Cottage, 2 Bedrooms, Lake View (Pet not allowed)

11. Head of Pond House

Head of Pond House
3.0 star property
Water Mill
10.0 out of 10, Exceptional, (13 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 AU$1,717
includes taxes & fees
14 Sept - 15 Sept
Head of Pond House
Smart TV, stereo, offices

12. Azur East, southampton

Azur East, southampton
Southampton
The price is AU$921
includes taxes & fees
14 Sept - 15 Sept
Azur East, southampton
Beach nearby, sun-loungers, beach umbrellas, beach towels

13. The Hedges Inn

The Hedges Inn
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (79 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 AU$798
includes taxes & fees
14 Sept - 15 Sept
The Hedges Inn
Property grounds

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

Pool tennis gym Bikes all included & <2m’s fr/ all
Southampton
The price is AU$567
includes taxes & fees
15 Sept - 16 Sept
Pool tennis gym Bikes all included & <2m’s fr/ all
Front of property – evening/night

15. 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 AU$1,764
includes taxes & fees
14 Sept - 15 Sept
Mill House Inn
Smart TV, offices

16. Pool Gym Biocharger Tennis Private bath All New BR

Pool Gym Biocharger Tennis Private bath All New BR
Southampton
The price is AU$1,012
includes taxes & fees
14 Sept - 15 Sept
Pool Gym Biocharger Tennis Private bath All New BR
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 AU$1,094
includes taxes & fees
14 Sept - 15 Sept
Free ride to Shinnecock Golf, SH Town or SH beache
Smart TV, video games, offices

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

Home 2 mins. from Shinnecock Golf town SH beaches
Southampton
The price is AU$1,106
includes taxes & fees
14 Sept - 15 Sept
Home 2 mins. from Shinnecock Golf town SH beaches
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southold Hotel Reviews

Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
"This looks like a motel from the outside but don't let that fool you. It's actually a beautifully done property inside the rooms. Very chic, new and modern features. I would definitely stay again and again"
Tiffany 1-night trip
Posted 10 hours ago
Greenview Inn Riverhead

Find out more about Southold

Southold B&B information

Number of reviews
311
Accommodation
46 B&B
Lowest Price
AU$362
Highest Price
AU$1,764

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 Huntting Inn: 19 rooms. Located 14.4 mi (23.1 km) from the core of Southold. Enjoy the fireplace in reception and bar/lounge.
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.

Explore a world of travel with Expedia