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Check prices for these dates

Next weekend
Oct 31 - Nov 2
In two weeks
Nov 7 - Nov 9
In one month
Nov 21 - Nov 23
In two months
Dec 19 - Dec 21

B&B in Southold

Exterior
The Sagaponack
The Sagaponack
3.0 star property
8.8 out of 10, Excellent, (194)
"The room was spotless and had everything that you would need. Would stay here again."
United States
Marjorie
The price is ￥23,740
￥33,198 total
includes taxes & fees
Oct 30 - Oct 31
The Sagaponack
IPod dock, MP3 dock
The Captain Stannard
The Captain Stannard
3.0 star property
9.6 out of 10, Exceptional, (252)
"Amazing stay! Everything was perfect and it is clear that the owners love their jobs and their inn. Can't wait to go back! "
United States
Julie
The Captain Stannard
Property grounds
Carole's Place B & B
Carole's Place B & B
3.0 star property
9.8 out of 10, Exceptional, (60)
"Small B&B with a charming old school vibe. Second time we’ve stayed there and we will return."
United States
Frank
The price is ￥22,889
￥26,150 total
includes taxes & fees
Oct 26 - Oct 27
Carole's Place B & B
Front of property - evening/night
Mill House Inn
Mill House Inn
5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
United States
Brian
The price is ￥49,371
￥62,048 total
includes taxes & fees
Oct 30 - Oct 31
Mill House Inn
Terrace/patio
Westbrook Inn B&B
Westbrook Inn B&B
3.0 star property
9.8 out of 10, Exceptional, (173)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is ￥33,190
￥36,841 total
includes taxes & fees
Oct 30 - Oct 31
Westbrook Inn B&B
Aerial view
East Hampton Art House Bed & Breakfast
East Hampton Art House Bed & Breakfast
4.0 star property
9.6 out of 10, Exceptional, (65)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
United States
Dan
The price is ￥57,695
￥65,916 total
includes taxes & fees
Oct 30 - Oct 31
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
9.2 out of 10, Wonderful, (19)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
United States
Rachel
The price is ￥46,093
￥51,164 total
includes taxes & fees
Oct 26 - Oct 27
James Pharmacy Bed & Breakfast
Room, 1 King Bed, Patio, Ground Floor (7) | Egyptian cotton sheets, premium bedding, down comforters
The Homestead
The Homestead
3.0 star property
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 ￥45,490
￥50,493 total
includes taxes & fees
Oct 26 - Oct 27
The Homestead
Exterior
Head of Pond House
Head of Pond House
3.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful place with a very kind host. Highly recommend this place!"
United States
Michèle
The price is ￥79,980
￥91,378 total
includes taxes & fees
Oct 26 - Oct 27
Head of Pond House
Garden
The Huntting Inn
The Huntting Inn
3.5 star property
9.0 out of 10, Wonderful, (103)
"What a wonderful place to stay! The room was beautiful. The bed was comfortable and the staff were welcoming and helpful. We loved how close it was to town. We also enjoyed the breakfast every morning. The Palm restaurant downstairs was nice to have on property and the food was great. We will definitely stay again!"
United States
Dena
The price is ￥58,106
￥67,904 total
includes taxes & fees
Nov 6 - Nov 7
The Huntting Inn
Porch
Harpoon House
Harpoon House
3.0 star property
8.4 out of 10, Very Good, (146)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
United States
Karissa
The price is ￥48,945
￥55,920 total
includes taxes & fees
Nov 9 - Nov 10
Harpoon House
Outdoor dining
Large Room w use of pool/tennis in Spacious home
Large Room w use of pool/tennis in Spacious home
The price is ￥86,817
￥125,223 total
includes taxes & fees
Oct 25 - Oct 26
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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Very nice staff, amenities great, an older place, but well kept. Wish there was more than 1 window, a bit stuffy. Felt safe in parking lot and in my room."
Michelle 3-night trip
Posted 3 days ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Southold

Southold B&B information

Number of reviews
1,158
Accommodation
38 B&B
Lowest Price
￥26,150
Highest Price
￥125,223

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. East Hampton Art House Bed & Breakfast: 2 rooms. Situated 13.9 mi (22.3 km) from the heart of Southold. Enjoy the free full breakfast and fitness center. Mill House Inn: 10 rooms. 14.3 mi (23.1 km) from the heart of downtown. Enjoy the free cooked breakfast and designer toiletries. 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 Croteaux Vineyards. You might put Osprey's Dominion 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.

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