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

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Check prices for these dates

Next weekend
31 July - 2 Aug
In two weeks
7 Aug - 9 Aug
In one month
21 Aug - 23 Aug
In two months
18 Sept - 20 Sept

Our top choices for Southold bed & breakfast

Deluxe Room, 1 King Bed

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (42 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$513
includes taxes & fees
26 July - 27 July
West Neck Guesthouse
Living area

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (268 reviews)
"Loved the beautiful porch and closeness to beach. The bed and linens were so comfortable."
United States
Judith
The price is AU$361
includes taxes & fees
3 Aug - 4 Aug
The Captain Stannard
Property entrance

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (276 reviews)
"Clean room, great staff, pool is nice and pet friendly."
United States
liliana
The price is AU$808
includes taxes & fees
26 July - 27 July
The Sagaponack
Fireplace

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (200 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$457
includes taxes & fees
27 July - 28 July
Westbrook Inn B&B
Interior detail

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (173 reviews)
"Not really any amenities but the location is unbeatable."
United States
Barbara
The price is AU$568
includes taxes & fees
21 July - 22 July
Harpoon House
Room, 1 King Bed, Patio, Ground Floor (2) | Terrace/patio

The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (95 reviews)
"Very enjoyable stay! Love the “house” guitar available to guests."
United States
Mary
The price is AU$420
includes taxes & fees
21 July - 22 July
The Homestead
Interior

The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.0 out of 10, Wonderful, (244 reviews)
"We had a wonderful stay. Perfect location, great staff, and check-in process, and our room was delightful."
United States
Brian
The price is AU$563
includes taxes & fees
21 July - 22 July
The Scranton Seahorse Inn
Beach nearby

The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (117 reviews)
"Amazing location, right on Main Street in East Hampton, great staff, rooms and breakfast"
United States
EDUARD
The price is AU$980
includes taxes & fees
2 Aug - 3 Aug
The Huntting Inn
Beach nearby, sun-loungers, beach umbrellas, beach towels

The Hedges Inn

The Hedges Inn
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (73 reviews)
"Excellent place"
United States
Miguel
The price is AU$1,261
includes taxes & fees
26 July - 27 July
The Hedges Inn
Front of property – evening/night

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (88 reviews)
"Couldn't have been nicer. Dawn and Tiffany were grcious and accomodating."
Canada
Ronald
The price is AU$1,791
includes taxes & fees
22 July - 23 July
Mill House Inn
Property grounds

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$1,560
includes taxes & fees
19 Aug - 20 Aug
Free ride to Shinnecock Golf, SH Town or SH beache
Property grounds

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$1,556
includes taxes & fees
19 Aug - 20 Aug
Pool tennis gym Bikes all included & <2m’s fr/ all
Smart TV, video games, offices

Home 2 mins. from Shinnecock Golf town SH beaches

Home 2 mins. from Shinnecock Golf town SH beaches
Southampton
The price is AU$1,475
includes taxes & fees
19 Aug - 20 Aug
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.
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Top Southold Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"rooms very dated but clean and roomy. location was excellent. staff very nice"
cindy 1-night trip
Posted 2 hours ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Southold

Southold B&B information

Number of reviews
1,403
Accommodation
46 B&B
Lowest Price
AU$361
Highest Price
AU$1,791

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. Mill House Inn: 10 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 on-site dining.
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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