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Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan
Interior entrance
Vine & Sand

Vine & Sand

3.0 star property
Southold
9.6 out of 10, Exceptional, (13)
"My husband and I escaped to Long Island for a beautiful fall weekend and thoroughly enjoyed our stay at Vine + Sand. The hosts were very friendly and helpful with restaurant reservations and offered great tips for local activities. The accommodations were eco-friendly, modern and super comfortable and the breakfast in the morning offered delicious pastries and other homemade foods from local bakeries and markets which were a great touch. The location was private yet close enough to get to town...
United States
Heather
Vine & Sand
Exterior
The Sagaponack

The Sagaponack

3.0 star property
Wainscott
8.8 out of 10, Excellent, (205)
"The room was spotless and had everything that you would need. Would stay here again."
United States
Marjorie
The price is HK$1,282
HK$1,776 total
includes taxes & fees
16 Nov - 17 Nov
The Sagaponack
Front of property – evening/night
Mill House Inn

Mill House Inn

5.0 star property
North Main Street Historic District
9.0 out of 10, Wonderful, (71)
"Delightful property and even more delightful staff. love staying here! "
United States
Brittany
The price is HK$2,331
HK$2,930 total
includes taxes & fees
8 Dec - 9 Dec
Mill House Inn
Terrace/patio
Westbrook Inn B&B

Westbrook Inn B&B

3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (175)
"Beautiful place and wonderful staff"
United States
Rebecca
The price is HK$1,690
HK$1,876 total
includes taxes & fees
18 Nov - 19 Nov
Westbrook Inn B&B
Aerial view
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)
"Very profesional, very good experiencia , the host the best , the property beatiful 100 porcent recomended"
United States
Yasmani
The price is HK$3,055
HK$3,490 total
includes taxes & fees
19 Nov - 20 Nov
East Hampton Art House Bed & Breakfast
Individually decorated, individually furnished, iron/ironing board
James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4.0 star property
Old Saybrook Center
9.2 out of 10, Wonderful, (20)
"Beautiful property in a great location, convenient to everything.Our room was clean and comfortable."
United States
Ray
The price is HK$2,347
HK$2,606 total
includes taxes & fees
26 Nov - 27 Nov
James Pharmacy Bed & Breakfast
IPod dock, MP3 dock
The Captain Stannard

The Captain Stannard

3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (256)
"Clean, friendly and delicious continental breakfast "
United States
Miriam
The Captain Stannard
Porch
Harpoon House

Harpoon House

3.0 star property
Southampton
8.4 out of 10, Very good, (147)
"Great spot!"
United States
Keith
Harpoon House
Seasonal outdoor pool
Head of Pond House

Head of Pond House

3.0 star property
Water Mill
10.0 out of 10, Exceptional, (2)
"Beautiful place with a very kind host. Highly recommend this place!"
United States
Michèle
The price is HK$4,091
HK$4,675 total
includes taxes & fees
24 Nov - 25 Nov
Head of Pond House
Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds
The Homestead

The Homestead

3.0 star property
Madison Center
10.0 out of 10, Exceptional, (87)
"This is our 2nd year staying at the Homestead B & B. We absolutely love it here! Great food, amenities galore, and just an awesome getaway!"
United States
Cynthia
The price is HK$2,085
HK$2,314 total
includes taxes & fees
15 Dec - 16 Dec
The Homestead
Garden
The Huntting Inn

The Huntting Inn

3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (104)
"Staff and management was very welcoming!"
United States
Sanailer
The price is HK$2,972
HK$3,474 total
includes taxes & fees
7 Dec - 8 Dec
The Huntting Inn
Outdoor dining
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 HK$4,441
HK$6,344 total
includes taxes & fees
15 Nov - 16 Nov
Large Room w use of pool/tennis in Spacious home
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
"Beautiful and unique property. We really enjoyed our weekend getaway "
Caryn 1-night trip
Posted 17 hours ago
Sound View Greenport

Find out more about Southold

Southold B&B information

Number of reviews
1,133
Accommodation
38 B&B
Lowest Price
HK$1,776
Highest Price
HK$6,344

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. Mill House Inn: 10 rooms. Situated 14.3 mi (23.1 km) from the heart of Southold. Enjoy the free cooked breakfast and designer toiletries. The Captain Stannard: 11 rooms. 15.2 mi (24.4 km) from the city centre. Enjoy the private garden and unique decor. Harpoon House: 9 rooms. Located 12.4 mi (19.9 km) from the core of Southold. Enjoy the bars and unique decor.
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 The Old Field Vineyards. You should put Horton Point Park and Sannino's Bella Vita Vineyard 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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