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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

B&B in Southold

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 AED 612
AED 846 total
includes taxes & fees
17 Nov - 18 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 AED 1,102
AED 1,385 total
includes taxes & fees
1 Dec - 2 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 AED 799
AED 887 total
includes taxes & fees
20 Nov - 21 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 AED 1,444
AED 1,650 total
includes taxes & fees
17 Nov - 18 Nov
East Hampton Art House Bed & Breakfast
Miss Anna James Room | 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 AED 1,110
AED 1,232 total
includes taxes & fees
16 Nov - 17 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 AED 1,934
AED 2,209 total
includes taxes & fees
16 Nov - 17 Nov
Head of Pond House
Room, 1 King Bed, Patio, Ground Floor (7) | Egyptian cotton sheets, premium bedding, down comforters
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 AED 986
AED 1,094 total
includes taxes & fees
1 Dec - 2 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 AED 1,405
AED 1,642 total
includes taxes & fees
30 Nov - 1 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 AED 2,099
AED 2,998 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

Madison Beach Hotel

Madison Beach Hotel

10/10 Excellent
"Everything was perfect!!!!!"
Evelyn 2-night trip
Posted 3 days ago
Madison Beach Hotel

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. 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 heart of downtown. Enjoy the private yard and unique décor. Harpoon House: 9 rooms. Located 12.4 mi (19.9 km) from the core of Southold. Enjoy the bars and unique décor.
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 The Old Field Vineyards. You might 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?
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.